Want to step into a living postcard? Chestertown, Maryland, has everything you want in a small coastal town: walkable historic streets, friendly people, unique eateries and indie shops that feel more like treasure hunts than retail.
Historic Chestertown Maryland
<img decoding=async class=wp image 17534 size full src=httpsonbetterlivingcomwp contentuploads202510Chestertown Maryland Waterfront B e1762372747142jpg alt=Scenic view of the Chester River waterfront in Chestertown Maryland framed by overhanging tree branches with bright green leaves A wooden park bench with ornate cast iron arms sits on a brick paver walkway in the foreground Natural landscaping with ornamental grasses and rocks lines the waters edge In the middle distance a historic tall ship with two masts is docked at a wooden pier alongside modern sailboats The river stretches wide under a brilliant blue sky filled with puffy white clouds with tree lined shores visible on the opposite bank width=1300 height=1638 srcset=httpsonbetterlivingcomwp contentuploads202510Chestertown Maryland Waterfront B e1762372747142jpg 1300w httpsonbetterlivingcomwp contentuploads202510Chestertown Maryland Waterfront B e1762372747142 238x300jpg 238w httpsonbetterlivingcomwp contentuploads202510Chestertown Maryland Waterfront B e1762372747142 952x1200jpg 952w httpsonbetterlivingcomwp contentuploads202510Chestertown Maryland Waterfront B e1762372747142 768x968jpg 768w httpsonbetterlivingcomwp contentuploads202510Chestertown Maryland Waterfront B e1762372747142 1219x1536jpg 1219w httpsonbetterlivingcomwp contentuploads202510Chestertown Maryland Waterfront B e1762372747142 500x630jpg 500w httpsonbetterlivingcomwp contentuploads202510Chestertown Maryland Waterfront B e1762372747142 293x369jpg 293w httpsonbetterlivingcomwp contentuploads202510Chestertown Maryland Waterfront B e1762372747142 770x970jpg 770w httpsonbetterlivingcomwp contentuploads202510Chestertown Maryland Waterfront B e1762372747142 390x491jpg 390w sizes=max width 1300px 100vw 1300px> Peaceful waterfront views along the Chester River in Chestertown MD with maritime charm on full display | Photo Better Living
Chestertown has a permanent spot on our must-visit list.
Nestled along the Chester River, Chestertown, on Maryland’s Eastern Shore, may be off the beaten path, but that’s exactly what makes it so special. With big character and historic colonial charm, this unique small town may be one of America’s coolest under-the-radar destinations.
Once an important port city founded in 1706 and nestled along the banks of the Chester River, today you can walk through peaceful brick-lined streets lined with 18th-century homes, visit historic landmarks, and shop your way through a town that feels like it was decorated for a Hallmark movie set. Except this one is real.
Chestertown’s downtown and historic district, listed on the National Register of Historic Places, is home to Washington College, the first college chartered in the United States in 1782.
This friendly town is full of character. And there’s plenty to do within a few square blocks. Looking for more Maryland Eastern Shore destinations? Explore nearby St. Michaels, MD and Kent Narrows.
Things to Do in Chestertown MD
<img loading=lazy decoding=async class=wp image 17587 size full src=httpsonbetterlivingcomwp contentuploads202511Chestertown Maryland Fountainjpg alt=Ornate Victorian era fountain painted in turquoise blue located in a town square in Chestertown Maryland The multi tiered cast iron fountain features elaborate scrollwork decorative flourishes and a female figure statue at the top Water flows from multiple levels into a circular basin below The fountain sits on brick pavement surrounded by a green lawn with mature trees providing dappled shade Historic buildings and parked cars are visible in the background under a clear blue sky width=1300 height=1726 srcset=httpsonbetterlivingcomwp contentuploads202511Chestertown Maryland Fountainjpg 1300w httpsonbetterlivingcomwp contentuploads202511Chestertown Maryland Fountain 226x300jpg 226w httpsonbetterlivingcomwp contentuploads202511Chestertown Maryland Fountain 904x1200jpg 904w httpsonbetterlivingcomwp contentuploads202511Chestertown Maryland Fountain 768x1020jpg 768w httpsonbetterlivingcomwp contentuploads202511Chestertown Maryland Fountain 1157x1536jpg 1157w httpsonbetterlivingcomwp contentuploads202511Chestertown Maryland Fountain 500x664jpg 500w httpsonbetterlivingcomwp contentuploads202511Chestertown Maryland Fountain 370x490jpg 370w httpsonbetterlivingcomwp contentuploads202511Chestertown Maryland Fountain 293x389jpg 293w httpsonbetterlivingcomwp contentuploads202511Chestertown Maryland Fountain 770x1022jpg 770w httpsonbetterlivingcomwp contentuploads202511Chestertown Maryland Fountain 390x518jpg 390w sizes=max width 1300px 100vw 1300px> The iconic Hebe fountain in downtown Chestertown a perfect spot to rest while exploring the historic district | Photo Better Living
Explore Historic Fountain Park
Start your day at Chestertown’s small but beautiful Fountain Park at the intersection of High and Cross Streets in the heart of town. A gathering place throughout the year, it’s also home to the Hebe Fountain, one of Chestertown’s iconic historic landmarks.
A symbol of the town’s timeless charm, it’s one of the many public art installations throughout the town.
Installed in 1899, made of cast iron, painted turquoise, and fully functional, you can’t miss it. Decorated beautifully with carved lions and swans, its standout feature is the Greek goddess of youth, Hebe, who pours “ambrosia” into a chalice at the fountain’s top.
Visit the Chestertown Farmers Market
Every Saturday from 8 to noon, here you’ll find the year-round Chestertown Farmers Market, where you can shop for local fresh produce, eggs, meat, dairy, flowers, baked goods, and artisan crafts.
Stroll the Historic Waterfront
<img loading=lazy decoding=async class=wp image 17590 size full src=httpsonbetterlivingcomwp contentuploads202511Chestertown Maryland Waterfront 3jpg alt=White wooden boardwalk pier extending over Chester River with gray railings on both sides blue sky with white clouds marina dock with boats visible in background trees lining waterfront peaceful water scene width=1300 height=979 srcset=httpsonbetterlivingcomwp contentuploads202511Chestertown Maryland Waterfront 3jpg 1300w httpsonbetterlivingcomwp contentuploads202511Chestertown Maryland Waterfront 3 300x226jpg 300w httpsonbetterlivingcomwp contentuploads202511Chestertown Maryland Waterfront 3 1200x904jpg 1200w httpsonbetterlivingcomwp contentuploads202511Chestertown Maryland Waterfront 3 768x578jpg 768w httpsonbetterlivingcomwp contentuploads202511Chestertown Maryland Waterfront 3 500x377jpg 500w httpsonbetterlivingcomwp contentuploads202511Chestertown Maryland Waterfront 3 293x221jpg 293w httpsonbetterlivingcomwp contentuploads202511Chestertown Maryland Waterfront 3 770x580jpg 770w httpsonbetterlivingcomwp contentuploads202511Chestertown Maryland Waterfront 3 390x294jpg 390w sizes=max width 1300px 100vw 1300px> Stroll Chestertowns peaceful waterfront boardwalk along the Chester River | Photo Better Living
If you’re visiting Chestertown for the first time, don’t miss the chance to stroll along its historic waterfront where you can enjoy shaded benches, river views, and a quiet place to relax with coffee or a picnic. It’s a popular birdwatching spot where ospreys, hooded mergansers, great blue herons, and other native birds make regular appearances.
Docked at the Chestertown Marina, you can also see the Schooner Sultana, a stunning replica of an 18th-century British Navy vessel. It’s often open for public sails or dockside tours during special events.
Take a River Cruise
For more time on the Chester River, book a cruise on The River Packet. This 65-foot, 1920s-style classic yacht and tour boat offers weekend brunch, dinner, sunset and casual tours April through November that leave right from the High Street Dock.
During the Christmas season, come for ‘A Dickens of a Christmas’ festival weekend where you can “step back into 1840s London and experience the holiday season as Charles Dickens imagined it.” Activities include complimentary carriage rides through historic downtown, a ticketed house tour, food vendors, an artisan village and an authentic Victorian tea time. Wearing your Victorian best is highly encouraged.
Get Cozy With Friendly Felines at the Cat Colloquium
<img loading=lazy decoding=async class=wp image 17591 size full src=httpsonbetterlivingcomwp contentuploads202511Cat Colloquium 2jpg alt=Cat Colloquium lounge interior with gray walls multiple resident cats lounging on furniture including orange tabby in pink chair and white cat on ottoman cat artwork on walls bookshelves TV screen showing aquarium cat tree and toys throughout modern space width=1300 height=1726 srcset=httpsonbetterlivingcomwp contentuploads202511Cat Colloquium 2jpg 1300w httpsonbetterlivingcomwp contentuploads202511Cat Colloquium 2 226x300jpg 226w httpsonbetterlivingcomwp contentuploads202511Cat Colloquium 2 904x1200jpg 904w httpsonbetterlivingcomwp contentuploads202511Cat Colloquium 2 768x1020jpg 768w httpsonbetterlivingcomwp contentuploads202511Cat Colloquium 2 1157x1536jpg 1157w httpsonbetterlivingcomwp contentuploads202511Cat Colloquium 2 500x664jpg 500w httpsonbetterlivingcomwp contentuploads202511Cat Colloquium 2 370x490jpg 370w httpsonbetterlivingcomwp contentuploads202511Cat Colloquium 2 293x389jpg 293w httpsonbetterlivingcomwp contentuploads202511Cat Colloquium 2 770x1022jpg 770w httpsonbetterlivingcomwp contentuploads202511Cat Colloquium 2 390x518jpg 390w sizes=max width 1300px 100vw 1300px> Meet the resident cats in the Cat Colloquiums cozy second floor lounge | Photo Better Living
Chestertown’s Cat Colloquium (215 High St #2C, Chestertown, MD 21620) run by nonprofit Kit Care Inc. is a warm, welcoming and unique spot for cat lovers. Here you can meet and snuggle up with resident cats, enjoy quiet time, or chat with their friendly volunteers.
Walk through the alley next to Stam’s Luncheonette and follow the signs to the second floor. The space is bright, peaceful and playful, with cozy seating, and cat-friendly furniture (including a life-sized cat tree).
It’s a true hidden gem and a unique experience if you’re an animal lover like us and can’t pass up an encounter with a furry friend. Visiting is free, but you can check out their blog and donation options to learn more and support them.
If you’re traveling with 6 people or more, make an appointment before you go.
Visit Lockbrier Farm for Fresh Produce and Homemade Ice Cream
<img loading=lazy decoding=async class=wp image 17592 size full src=httpsonbetterlivingcomwp contentuploads202511Lockbriar Farms Chestertown MD Fall 2025 2jpg alt=Lockbriar Farms autumn display with vintage green truck loaded with pumpkins and mums red and white striped tent canopies in background rows of colorful chrysanthemums in yellow burgundy orange and white arranged on ground fall harvest decorations with corn stalks width=1300 height=979 srcset=httpsonbetterlivingcomwp contentuploads202511Lockbriar Farms Chestertown MD Fall 2025 2jpg 1300w httpsonbetterlivingcomwp contentuploads202511Lockbriar Farms Chestertown MD Fall 2025 2 300x226jpg 300w httpsonbetterlivingcomwp contentuploads202511Lockbriar Farms Chestertown MD Fall 2025 2 1200x904jpg 1200w httpsonbetterlivingcomwp contentuploads202511Lockbriar Farms Chestertown MD Fall 2025 2 768x578jpg 768w httpsonbetterlivingcomwp contentuploads202511Lockbriar Farms Chestertown MD Fall 2025 2 500x377jpg 500w httpsonbetterlivingcomwp contentuploads202511Lockbriar Farms Chestertown MD Fall 2025 2 293x221jpg 293w httpsonbetterlivingcomwp contentuploads202511Lockbriar Farms Chestertown MD Fall 2025 2 770x580jpg 770w httpsonbetterlivingcomwp contentuploads202511Lockbriar Farms Chestertown MD Fall 2025 2 390x294jpg 390w sizes=max width 1300px 100vw 1300px> Lockbriar Farms bursts with fall colors and fresh seasonal produce | Photo Better Living
For a farm experience, an eight-minute drive from downtown Chestertown, go to Lockbrier Farm to pick berries, flowers and pumpkins, savor farm-churned ice cream, and stock up on fresh, local and seasonal produce.
Since 1993, the Lockwood family—whose farming roots stretch back to the Civil War—has opened the gates of Lockbrier Farms (10051 Worton Rd, Chestertown, MD 21620) to visitors seeking fresh air, vibrant blooms, and the joy of picking their own seasonal produce.
During our recent fall visit, they were brimming with mums, pumpkins, Indian corn and gourds in every color. Seasonally, you can pick your own fruits like strawberries, blueberries, raspberries, and blackberries. Wander through their flower and herb gardens, where you can cut your own to create your own DIY bouquet.
Then shop the farm stand and stock up on fresh produce, apple cider, jams, pickled veggies, local honey, and treats like apple butter, eggs and fresh cheese.
After exploring the farm, head over to their ice cream barn for a scoop of their incredible homemade ice cream in 28+ rotating flavors like strawberry and lemon cookie. It’s made on-site with Lockbrier’s own grown and locally sourced ingredients and is some of the best in Kent County.
Lockbrier Farm is open daily (weather permitting), May through Thanksgiving, and there’s no admission fee. Wear boots you won’t mind getting dirty if you plan to explore the fields.
Where to Shop in Chestertown MD
<img loading=lazy decoding=async class=wp image 17535 size full src=httpsonbetterlivingcomwp contentuploads202510Historic Chestertown MD Fall 2025jpg alt=Fall street scene in historic Chestertown Maryland showing The Bookplate independent bookstore with red and cream striped awning brick sidewalk with pumpkins and hay bale decorations Book Plate hanging sign neighboring shops including Twigs and Teacups autumn tree with orange leaves chalkboard sign with black cat width=1300 height=1727 srcset=httpsonbetterlivingcomwp contentuploads202510Historic Chestertown MD Fall 2025jpg 1300w httpsonbetterlivingcomwp contentuploads202510Historic Chestertown MD Fall 2025 226x300jpg 226w httpsonbetterlivingcomwp contentuploads202510Historic Chestertown MD Fall 2025 903x1200jpg 903w httpsonbetterlivingcomwp contentuploads202510Historic Chestertown MD Fall 2025 768x1020jpg 768w httpsonbetterlivingcomwp contentuploads202510Historic Chestertown MD Fall 2025 1156x1536jpg 1156w httpsonbetterlivingcomwp contentuploads202510Historic Chestertown MD Fall 2025 500x664jpg 500w httpsonbetterlivingcomwp contentuploads202510Historic Chestertown MD Fall 2025 293x389jpg 293w httpsonbetterlivingcomwp contentuploads202510Historic Chestertown MD Fall 2025 770x1023jpg 770w httpsonbetterlivingcomwp contentuploads202510Historic Chestertown MD Fall 2025 390x518jpg 390w sizes=max width 1300px 100vw 1300px> Downtown Chestertowns brick lined streets come alive with fall charm | Photo Better Living
If you’re bored with cookie-cutter tourist traps, you’ll love Chestertown’s authentically independent spirit. It has 200 locally owned shops, galleries, restaurants, bakeries, and cafes where you can take your time browsing handmade goods, rare books and discovering one-of-a-kind finds.
Twigs & Teacups
<img loading=lazy decoding=async class=wp image 17593 size full src=httpsonbetterlivingcomwp contentuploads202511Twigs Teacups Chestertown MD 1jpg alt=Twigs and Teacups gift shop interior display showing eclectic home goods including woven basket black poodle figurines in wooden bowl gold dome lamp flatware set think like a chef cookbook decorative candles orange placemats patterned mugs colorful linens and kitchen accessories arranged on counter with bookshelves visible in background width=1300 height=1727 srcset=httpsonbetterlivingcomwp contentuploads202511Twigs Teacups Chestertown MD 1jpg 1300w httpsonbetterlivingcomwp contentuploads202511Twigs Teacups Chestertown MD 1 226x300jpg 226w httpsonbetterlivingcomwp contentuploads202511Twigs Teacups Chestertown MD 1 903x1200jpg 903w httpsonbetterlivingcomwp contentuploads202511Twigs Teacups Chestertown MD 1 768x1020jpg 768w httpsonbetterlivingcomwp contentuploads202511Twigs Teacups Chestertown MD 1 1156x1536jpg 1156w httpsonbetterlivingcomwp contentuploads202511Twigs Teacups Chestertown MD 1 500x664jpg 500w httpsonbetterlivingcomwp contentuploads202511Twigs Teacups Chestertown MD 1 293x389jpg 293w httpsonbetterlivingcomwp contentuploads202511Twigs Teacups Chestertown MD 1 770x1023jpg 770w httpsonbetterlivingcomwp contentuploads202511Twigs Teacups Chestertown MD 1 390x518jpg 390w sizes=max width 1300px 100vw 1300px> Twigs Teacups overflows with whimsical gifts and unique home goods | Photo Better Living
If you only have time to go into one store in Chestertown, make it Twigs & Teacups (111 S Cross St, Chestertown, MD 21620). Everyone we asked for local recommendations said it was their favorite store.
Way bigger than it looks from the outside, this 2-story shop is filled with a curated collection of whimsical and unique gifts packed with personality, including everything from quirky kitchenware and nostalgic toys to locally made goods, stationery, books, puzzles, clothing and seasonal treasures. Give yourself plenty of time to browse, because there’s so much to see.
Pricing is affordable, and the friendly staff, which includes their resident cat Jonathan, will help you find a unique gift for any occasion.
Chester River Wine & Cheese Co.
<img loading=lazy decoding=async class=wp image 17594 size full src=httpsonbetterlivingcomwp contentuploads202511Chester River Wine Cheese Co3 e1762401397919jpg alt= Interior of Chester River Wine Cheese Co showing wire shelving filled with gourmet products including colorful pasta packages and specialty items on a turquoise shelf unit In the foreground a black wire rack displays multiple glass bottles of infused olive oils with pour spouts for sampling alongside rows of small jars containing flavored honey in golden and amber hues Additional shelves in the background hold various gourmet food products Warm yellow walls and natural light from windows create an inviting atmosphere width=1300 height=1597 srcset=httpsonbetterlivingcomwp contentuploads202511Chester River Wine Cheese Co3 e1762401397919jpg 1300w httpsonbetterlivingcomwp contentuploads202511Chester River Wine Cheese Co3 e1762401397919 244x300jpg 244w httpsonbetterlivingcomwp contentuploads202511Chester River Wine Cheese Co3 e1762401397919 977x1200jpg 977w httpsonbetterlivingcomwp contentuploads202511Chester River Wine Cheese Co3 e1762401397919 768x943jpg 768w httpsonbetterlivingcomwp contentuploads202511Chester River Wine Cheese Co3 e1762401397919 1250x1536jpg 1250w httpsonbetterlivingcomwp contentuploads202511Chester River Wine Cheese Co3 e1762401397919 500x614jpg 500w httpsonbetterlivingcomwp contentuploads202511Chester River Wine Cheese Co3 e1762401397919 293x360jpg 293w httpsonbetterlivingcomwp contentuploads202511Chester River Wine Cheese Co3 e1762401397919 770x946jpg 770w httpsonbetterlivingcomwp contentuploads202511Chester River Wine Cheese Co3 e1762401397919 390x479jpg 390w sizes=max width 1300px 100vw 1300px> Sampling the incredible selection of infused olive oils and artisan foods at Chester River Wine Cheese Co
A few doors down, foodies and wine lovers must pop into Chester River Wine & Cheese Co. (117 S Cross St, Chestertown, MD 21620) This cozy gourmet shop and local favorite offers a curated selection of wines from around the world, and cut-to-order cheeses, charcuterie, olives, pickles, jam, snacks and specialty items. Build a picnic to take to the riverfront or gather snacks for winding down later.
The staff here are happy to offer pairings or samples, and the shop often hosts tastings and seasonal events. Whether you want a new wine to try or you’re a fromage fanatic, this shop is a delicious detour.
The Bookplate
<img loading=lazy decoding=async class=wp image 17595 size full src=httpsonbetterlivingcomwp contentuploads202511Book Plate Chestertown MD 3jpg alt=Interior of The Bookplate independent bookstore in Chestertown Maryland showing white bookshelves filled with childrens books including The Three Pigs Ghostly Terrors and Halloween books with a large white decorative rabbit statue whimsical wall mural with stars and houses in background width=1300 height=1727 srcset=httpsonbetterlivingcomwp contentuploads202511Book Plate Chestertown MD 3jpg 1300w httpsonbetterlivingcomwp contentuploads202511Book Plate Chestertown MD 3 226x300jpg 226w httpsonbetterlivingcomwp contentuploads202511Book Plate Chestertown MD 3 903x1200jpg 903w httpsonbetterlivingcomwp contentuploads202511Book Plate Chestertown MD 3 768x1020jpg 768w httpsonbetterlivingcomwp contentuploads202511Book Plate Chestertown MD 3 1156x1536jpg 1156w httpsonbetterlivingcomwp contentuploads202511Book Plate Chestertown MD 3 500x664jpg 500w httpsonbetterlivingcomwp contentuploads202511Book Plate Chestertown MD 3 293x389jpg 293w httpsonbetterlivingcomwp contentuploads202511Book Plate Chestertown MD 3 770x1023jpg 770w httpsonbetterlivingcomwp contentuploads202511Book Plate Chestertown MD 3 390x518jpg 390w sizes=max width 1300px 100vw 1300px> The Bookplates charming childrens section features whimsical finds and rare titles | Photo Better Living
Book lovers should head across the street, where they can get lost in the shelves at The Bookplate (112 S Cross St, Chestertown, MD 21620).
This independent used bookstore, which also sells vintage prints and pottery, has an enormous selection with a wide variety of genres and hard to find titles. The selection here is truly one of a kind, and the books are well organized. If there’s something you want but don’t see, ask the staff, and they may have it hidden in the stacks or can special order it.
Where to Eat in Chestertown MD
With so much to do here, there’s no doubt you’ll get hungry. When you want to eat, Chestertown has a delicious mix of options, from Chesapeake seafood, farm-to-table fare, international flavors, casual eats and cozy comfort food.
Stam’s Luncheonette
<img loading=lazy decoding=async class=wp image 17596 size full src=httpsonbetterlivingcomwp contentuploads202511Stams Chestertown MDjpg alt=Stams Luncheonette exterior showing historic white two story building with black shutters curved bay windows on first floor red door entrance bright yellow metal bistro tables and chairs on brick plaza ice cream cone sign blue sky width=1300 height=1727 srcset=httpsonbetterlivingcomwp contentuploads202511Stams Chestertown MDjpg 1300w httpsonbetterlivingcomwp contentuploads202511Stams Chestertown MD 226x300jpg 226w httpsonbetterlivingcomwp contentuploads202511Stams Chestertown MD 903x1200jpg 903w httpsonbetterlivingcomwp contentuploads202511Stams Chestertown MD 768x1020jpg 768w httpsonbetterlivingcomwp contentuploads202511Stams Chestertown MD 1156x1536jpg 1156w httpsonbetterlivingcomwp contentuploads202511Stams Chestertown MD 500x664jpg 500w httpsonbetterlivingcomwp contentuploads202511Stams Chestertown MD 293x389jpg 293w httpsonbetterlivingcomwp contentuploads202511Stams Chestertown MD 770x1023jpg 770w httpsonbetterlivingcomwp contentuploads202511Stams Chestertown MD 390x518jpg 390w sizes=max width 1300px 100vw 1300px> Stams Luncheonette serves nostalgic comfort food in a restored historic soda fountain | Photo Better Living
For a casual bite, Stam’s Luncheonette (215 High Street, Chestertown, MD 21620) is a retro-style lunch counter, soda fountain and ice cream shop in a restored space that was originally Chester Pharmacy, opened by a local named John Stam about 175 years ago.
The mantra here is nostalgic charm serving up casual and classic American lunch staples like Pizza Grilled Cheese, Dill Chicken Salad sandwiches and tomato soup. Our favorite is their famous signature juicy Butter Burger served with cheddar cheese, caramelized onions, and on a buttery toasted brioche bun. It’s oh so buttery and worth every darn calorie.
A local favorite is their in-house made ice cream and sundaes made with creative rotating seasonal flavors like Oatmilk Chai and Honeycomb + Graham Cracker. They even have pints of ice cream to go. It’s a must-stop if you’re craving cozy comfort food with flavors that never go out of style.
The Kitchen at the Imperial
<img loading=lazy decoding=async class=wp image 17589 size full src=httpsonbetterlivingcomwp contentuploads202511The Kitchen Chestertown MD Crab Cake e1762380153817jpg alt=lose up of a golden brown jumbo lump crab cake with crispy edges on a white plate accompanied by a side of sautéed zucchini and corn succotash A ramekin of orange remoulade sauce and what appears to be coleslaw are visible in the background A silver fork rests on the right side of the plate The crab cake shows large chunks of premium crab meat with minimal filler and a perfectly seared crust width=1300 height=1660 srcset=httpsonbetterlivingcomwp contentuploads202511The Kitchen Chestertown MD Crab Cake e1762380153817jpg 1300w httpsonbetterlivingcomwp contentuploads202511The Kitchen Chestertown MD Crab Cake e1762380153817 235x300jpg 235w httpsonbetterlivingcomwp contentuploads202511The Kitchen Chestertown MD Crab Cake e1762380153817 940x1200jpg 940w httpsonbetterlivingcomwp contentuploads202511The Kitchen Chestertown MD Crab Cake e1762380153817 768x981jpg 768w httpsonbetterlivingcomwp contentuploads202511The Kitchen Chestertown MD Crab Cake e1762380153817 1203x1536jpg 1203w httpsonbetterlivingcomwp contentuploads202511The Kitchen Chestertown MD Crab Cake e1762380153817 500x638jpg 500w httpsonbetterlivingcomwp contentuploads202511The Kitchen Chestertown MD Crab Cake e1762380153817 293x374jpg 293w httpsonbetterlivingcomwp contentuploads202511The Kitchen Chestertown MD Crab Cake e1762380153817 770x983jpg 770w httpsonbetterlivingcomwp contentuploads202511The Kitchen Chestertown MD Crab Cake e1762380153817 390x498jpg 390w sizes=max width 1300px 100vw 1300px> The award winning crab cake at The Kitchen at Imperial a must try when visiting Marylands Eastern Shore | Photo Better Living
After 25 years in the tech world, Chef Steve Quigg traded IT consulting for culinary creativity, and is the heart behind The Kitchen at the Imperial (208 High Street, Chestertown, MD 21620). It’s one of Chestertown’s most beloved casual upscale dining spots, where every dish feels like a celebration of the Eastern Shore.
Winner of Best Chef on the Eastern Shore three years in a row, Chef Steve crafts his farm-to-table menu inspired by what’s harvested fresh from both the local farms and waterways. The menu changes here often, and everything from the dinner rolls and hand-cut fries and desserts is made in-house.
A must-try here is the Braised Lamb Shank and the signature crab cakes with absolutely no filler, packed with fresh lump crabmeat, perfectly seasoned and paired with local produce and house-made sauces for an elevated twist. They’ve won multiple awards for ‘Best Crab Cake’, including honors from What’s Up? Magazine and Chesapeake Bay Magazine. Pair it with their Rosemary Grapefruit Margarita or a glass of wine from their extensive curated international wine list.
Open for lunch, dinner and brunch on Sundays, The Kitchen at the Imperial is closed Tuesdays.
Retriever Bar
<img loading=lazy decoding=async class=wp image 17540 size full src=httpsonbetterlivingcomwp contentuploads202510The Retriever Bar House Burgerjpg alt= Retriever Bar house burger on golden brioche bun with juicy grass fed beef patty melted white cheese shredded lettuce pickles and bistro sauce served with crispy hand cut fries on white plate width=1300 height=867 srcset=httpsonbetterlivingcomwp contentuploads202510The Retriever Bar House Burgerjpg 1300w httpsonbetterlivingcomwp contentuploads202510The Retriever Bar House Burger 300x200jpg 300w httpsonbetterlivingcomwp contentuploads202510The Retriever Bar House Burger 1200x800jpg 1200w httpsonbetterlivingcomwp contentuploads202510The Retriever Bar House Burger 768x512jpg 768w httpsonbetterlivingcomwp contentuploads202510The Retriever Bar House Burger 360x240jpg 360w httpsonbetterlivingcomwp contentuploads202510The Retriever Bar House Burger 500x333jpg 500w httpsonbetterlivingcomwp contentuploads202510The Retriever Bar House Burger 1155x770jpg 1155w httpsonbetterlivingcomwp contentuploads202510The Retriever Bar House Burger 370x247jpg 370w httpsonbetterlivingcomwp contentuploads202510The Retriever Bar House Burger 770x514jpg 770w httpsonbetterlivingcomwp contentuploads202510The Retriever Bar House Burger 293x195jpg 293w httpsonbetterlivingcomwp contentuploads202510The Retriever Bar House Burger 120x80jpg 120w httpsonbetterlivingcomwp contentuploads202510The Retriever Bar House Burger 240x160jpg 240w httpsonbetterlivingcomwp contentuploads202510The Retriever Bar House Burger 390x260jpg 390w sizes=max width 1300px 100vw 1300px> The Retriever Bars House Burger features locally raised grass fed beef | Photo Better Living
The 21 and over Retriever Bar (337 1/2 High Street, Chestertown, MD 21620) blends Chesapeake flavor with a modern lounge feel and craft cocktails. Cozy up in the lounge, grab a seat at the bar, which boasts one of the most extensive spirit selections in town, including rare bourbons and whiskeys.
It’s also Chestertown’s go-to spot for raw, locally sourced Chesapeake Bay oysters, small plates like Ceviche, Warm Goat Cheese and Pickled Beets and mains like Shrimp and Grits and Lamb Birria Tacos. Whether you’re sipping something bold or nibbling on a cheese board, everything is thoughtfully crafted here.
We love the House Burger – a juicy double smash burger with locally raised, grass-fed St. Brigid’s beef, American cheese, pickles, shredded lettuce slathered with bistro sauce served on a toasted brioche roll served with fries on the side.
For dessert, try their delicious Apple Strudel with a scoop of creamy vanilla ice cream from Stam’s Luncheonette.
El Rancho Mexican Cuisine
<img loading=lazy decoding=async class=wp image 17597 size full src=httpsonbetterlivingcomwp contentuploads202511El Rancho Chestertown MDjpg alt=Three authentic Mexican street tacos on warm corn tortillas with seasoned meat diced onions and fresh cilantro on red and white checkered paper served with cucumber slices radish lime wedges and small bowl of salsa verde on wooden board width=1300 height=896 srcset=httpsonbetterlivingcomwp contentuploads202511El Rancho Chestertown MDjpg 1300w httpsonbetterlivingcomwp contentuploads202511El Rancho Chestertown MD 300x207jpg 300w httpsonbetterlivingcomwp contentuploads202511El Rancho Chestertown MD 1200x827jpg 1200w httpsonbetterlivingcomwp contentuploads202511El Rancho Chestertown MD 768x529jpg 768w httpsonbetterlivingcomwp contentuploads202511El Rancho Chestertown MD 500x345jpg 500w httpsonbetterlivingcomwp contentuploads202511El Rancho Chestertown MD 293x202jpg 293w httpsonbetterlivingcomwp contentuploads202511El Rancho Chestertown MD 770x531jpg 770w httpsonbetterlivingcomwp contentuploads202511El Rancho Chestertown MD 390x269jpg 390w sizes=max width 1300px 100vw 1300px> El Rancho serves authentic Mexican street tacos with hand pressed tortillas | Photo Better Living
For authentic Mexican flavors, El Rancho Mexican Cuisine (851 Washington Ave, Chestertown, MD 21620) is a few minutes outside downtown. Opening early (6:30 AM most days) it’s one of the few places in town where you can grab a full hot breakfast. The authentic Mexican menu offers everything from omelets and pancakes to quesadillas, burritos, fajitas, and bowls and platters.
We love the tender steak and flavorful Al Pastor Mexican Street Tacos here, which are served in warm, hand-pressed tortillas. We also ordered the chicken enchiladas, ½ red and ½ green, served with black beans. They were delicious, satisfying and really packed some heat.
See also
El Rancho is casual, affordable, and perfect for travelers craving bold flavors in a laid-back setting. Our server, Jordan, was super friendly, and we’re excited to try the spicy watermelon margarita next visit. El Rancho is open 7 days a week for breakfast, lunch and dinner.
Modern Stone Age Kitchen
<img loading=lazy decoding=async class=wp image 17598 size full src=httpsonbetterlivingcomwp contentuploads202511Modern Stoneage Kitchen 2 e1762401586938jpg alt=Behind the scenes view of Modern Stoneage Kitchen bakery showing professional bakers working at a large wooden table preparing dough Wire shelving racks in the foreground display dozens of freshly baked artisan bread loaves with golden brown crusts dusted with flour A brick oven is visible in the background along with stainless steel commercial baking equipment The industrial kitchen features polished concrete floors and bright overhead lighting width=1300 height=1310 srcset=httpsonbetterlivingcomwp contentuploads202511Modern Stoneage Kitchen 2 e1762401586938jpg 1300w httpsonbetterlivingcomwp contentuploads202511Modern Stoneage Kitchen 2 e1762401586938 298x300jpg 298w httpsonbetterlivingcomwp contentuploads202511Modern Stoneage Kitchen 2 e1762401586938 1191x1200jpg 1191w httpsonbetterlivingcomwp contentuploads202511Modern Stoneage Kitchen 2 e1762401586938 150x150jpg 150w httpsonbetterlivingcomwp contentuploads202511Modern Stoneage Kitchen 2 e1762401586938 768x774jpg 768w httpsonbetterlivingcomwp contentuploads202511Modern Stoneage Kitchen 2 e1762401586938 500x504jpg 500w httpsonbetterlivingcomwp contentuploads202511Modern Stoneage Kitchen 2 e1762401586938 293x295jpg 293w httpsonbetterlivingcomwp contentuploads202511Modern Stoneage Kitchen 2 e1762401586938 770x776jpg 770w httpsonbetterlivingcomwp contentuploads202511Modern Stoneage Kitchen 2 e1762401586938 390x393jpg 390w sizes=max width 1300px 100vw 1300px> Fresh artisan bread cooling at Modern Stoneage Kitchen in downtown Chestertown
Here you can buy sourdough breads, bagels, croissants, pastries and scratch-made meals for breakfast and lunch prepared according to ancestral food traditions made with ingredients like organic flour and lard and cooking techniques like fermentation that create the most nutrient-dense foods.
Our favorite is their delicious hand-rolled sourdough pretzels, which sell out fast. You can also grab refrigerated prepared foods to go like fermented veggies, yogurt, cheeses and house-made liverwurst.
Bakery seating is available inside, but it fills up quickly. When it’s warm, head to their pretty courtyard outside. If you’re interested, check their calendar of classes to learn ancient food prep skills like sourdough baking and fermentation.
Where to Stay in Chestertown MD
<img loading=lazy decoding=async class=wp image 17610 size full src=httpsonbetterlivingcomwp contentuploads202511Brampton Front Fall Night 2025jpg alt=Brampton 1860 historic brick inn at dusk with starry night sky showing three story red brick building with white wraparound porch glowing windows decorative fountain in manicured garden with colorful flowers trees on either side width=1300 height=1727 srcset=httpsonbetterlivingcomwp contentuploads202511Brampton Front Fall Night 2025jpg 1300w httpsonbetterlivingcomwp contentuploads202511Brampton Front Fall Night 2025 226x300jpg 226w httpsonbetterlivingcomwp contentuploads202511Brampton Front Fall Night 2025 903x1200jpg 903w httpsonbetterlivingcomwp contentuploads202511Brampton Front Fall Night 2025 768x1020jpg 768w httpsonbetterlivingcomwp contentuploads202511Brampton Front Fall Night 2025 1156x1536jpg 1156w httpsonbetterlivingcomwp contentuploads202511Brampton Front Fall Night 2025 500x664jpg 500w httpsonbetterlivingcomwp contentuploads202511Brampton Front Fall Night 2025 293x389jpg 293w httpsonbetterlivingcomwp contentuploads202511Brampton Front Fall Night 2025 770x1023jpg 770w httpsonbetterlivingcomwp contentuploads202511Brampton Front Fall Night 2025 390x518jpg 390w sizes=max width 1300px 100vw 1300px> Brampton 1860s stunning 19th century architecture glows against a starlit Eastern Shore sky | Photo Better Living
Brampton 1860
Stay longer and wake up at a luxurious historic 19th-century boutique inn on a lush private 35-acre estate, 1 mile from downtown Chestertown at Brampton 1860.
A TripAdvisor Traveler’s Choice Winner, featured on The Viewpoint with Dennis Quaid listed on the Select Registry, Brampton 1860’s (25227 Chestertown Road Chestertown, MD 21620) perfectly restored historic architecture, tranquil atmosphere, authentic hospitality and attention to detail have earned it top ratings and a loyal following.
<img loading=lazy decoding=async class=wp image 17271 size full src=httpsonbetterlivingcomwp contentuploads202509Brampton 1860 Inn Marleys Cottage 2jpg alt=Inside Marleys Cottage at Brampton 1860 with king bed cozy furnishings red accent wall fireplace and French doors opening to a private patio width=1300 height=1045 srcset=httpsonbetterlivingcomwp contentuploads202509Brampton 1860 Inn Marleys Cottage 2jpg 1300w httpsonbetterlivingcomwp contentuploads202509Brampton 1860 Inn Marleys Cottage 2 300x241jpg 300w httpsonbetterlivingcomwp contentuploads202509Brampton 1860 Inn Marleys Cottage 2 1200x965jpg 1200w httpsonbetterlivingcomwp contentuploads202509Brampton 1860 Inn Marleys Cottage 2 768x617jpg 768w httpsonbetterlivingcomwp contentuploads202509Brampton 1860 Inn Marleys Cottage 2 500x402jpg 500w httpsonbetterlivingcomwp contentuploads202509Brampton 1860 Inn Marleys Cottage 2 293x236jpg 293w httpsonbetterlivingcomwp contentuploads202509Brampton 1860 Inn Marleys Cottage 2 770x619jpg 770w httpsonbetterlivingcomwp contentuploads202509Brampton 1860 Inn Marleys Cottage 2 390x314jpg 390w sizes=max width 1300px 100vw 1300px> Inside Marleys Cottage at Brampton 1860 | Photo Better Living
Wake up in one of the seven thoughtfully appointed rooms and suites in the main house or six private cottages scattered throughout the property. Each has luxurious amenities like spa tubs, fireplaces, luxurious Comphy™ linens, smart TVs and free Wi-Fi.
Each morning, enjoy a freshly prepared multi-course gourmet à la carte breakfast in their sunlit dining room with menu options like Lemon Croissant French Toast and Apple Pancakes that change daily. Have it served on their sprawling porch, deck or breakfast room. Seasonal ingredients, homemade pastries, and warm hospitality are always included.
<img loading=lazy decoding=async class=wp image 17543 size full src=httpsonbetterlivingcomwp contentuploads202510Brampton Fall 2025 Breakfast Pancakesjpg alt=Stack of three golden buttermilk pancakes dusted with powdered sugar on white plate with blue rim garnished with fresh strawberries and blackberries served with crispy bacon strips and small bowl of maple syrup on white linen placematCaption width=1300 height=867 srcset=httpsonbetterlivingcomwp contentuploads202510Brampton Fall 2025 Breakfast Pancakesjpg 1300w httpsonbetterlivingcomwp contentuploads202510Brampton Fall 2025 Breakfast Pancakes 300x200jpg 300w httpsonbetterlivingcomwp contentuploads202510Brampton Fall 2025 Breakfast Pancakes 1200x800jpg 1200w httpsonbetterlivingcomwp contentuploads202510Brampton Fall 2025 Breakfast Pancakes 768x512jpg 768w httpsonbetterlivingcomwp contentuploads202510Brampton Fall 2025 Breakfast Pancakes 360x240jpg 360w httpsonbetterlivingcomwp contentuploads202510Brampton Fall 2025 Breakfast Pancakes 500x333jpg 500w httpsonbetterlivingcomwp contentuploads202510Brampton Fall 2025 Breakfast Pancakes 1155x770jpg 1155w httpsonbetterlivingcomwp contentuploads202510Brampton Fall 2025 Breakfast Pancakes 370x247jpg 370w httpsonbetterlivingcomwp contentuploads202510Brampton Fall 2025 Breakfast Pancakes 770x514jpg 770w httpsonbetterlivingcomwp contentuploads202510Brampton Fall 2025 Breakfast Pancakes 293x195jpg 293w httpsonbetterlivingcomwp contentuploads202510Brampton Fall 2025 Breakfast Pancakes 120x80jpg 120w httpsonbetterlivingcomwp contentuploads202510Brampton Fall 2025 Breakfast Pancakes 240x160jpg 240w httpsonbetterlivingcomwp contentuploads202510Brampton Fall 2025 Breakfast Pancakes 390x260jpg 390w sizes=max width 1300px 100vw 1300px> Brampton 1860s gourmet à la carte breakfast features daily specials like fluffy pancakes | Photo Better Living
Throughout the day, help yourself to a selection of baked goods and then return in the afternoon for their Afternoon Tea for delicious small plates, dessert, complimentary wine, coffee and tea. After breakfast, visit their flock of chickens and then walk through Brampton’s formal gardens with fruit trees, trails and wild meadows that attract birds, butterflies, and small wildlife.
At night, curl up with a book by the fireplace, do a puzzle in the library or enjoy a glass of wine in their bar and lounge. We love relaxing by the outdoor firepit where we can see tons of stars. Don’t be surprised if their cat Squeaky comes by to keep you company.
<img loading=lazy decoding=async class=wp image 17600 size full src=httpsonbetterlivingcomwp contentuploads202511Brampton Fall Library 2025jpg alt=Cozy library room at Brampton 1860 with floor to ceiling white built in bookshelves brown leather sofa with rust colored pillows arched fireplace with white mantel decorated with fall pumpkins and dried flowers oriental rug table lamps and large window with yellow curtains width=1300 height=979 srcset=httpsonbetterlivingcomwp contentuploads202511Brampton Fall Library 2025jpg 1300w httpsonbetterlivingcomwp contentuploads202511Brampton Fall Library 2025 300x226jpg 300w httpsonbetterlivingcomwp contentuploads202511Brampton Fall Library 2025 1200x904jpg 1200w httpsonbetterlivingcomwp contentuploads202511Brampton Fall Library 2025 768x578jpg 768w httpsonbetterlivingcomwp contentuploads202511Brampton Fall Library 2025 500x377jpg 500w httpsonbetterlivingcomwp contentuploads202511Brampton Fall Library 2025 293x221jpg 293w httpsonbetterlivingcomwp contentuploads202511Brampton Fall Library 2025 770x580jpg 770w httpsonbetterlivingcomwp contentuploads202511Brampton Fall Library 2025 390x294jpg 390w sizes=max width 1300px 100vw 1300px> Curl up with a book in Brampton 1860s inviting library by the fireplace | Photo Better Living
With personalized service, Brampton 1860 offers a unique experience that feels both timeless and welcoming. And you’ll have the best of both worlds: accommodations at a peaceful, luxurious, historic countryside estate and the convenience of Chestertown’s indie shops, galleries, and restaurants just 5 minutes away. Brampton is adults-only and pet-friendly. EV charging stations are available. For the best rates, book direct.
On Maryland’s Eastern Shore in Kent County, Chestertown is:
1 hour from Wilmington, DE
1.5 hours from Baltimore
1.5 hours from Washington, D.C.
1.5 hours from Philadelphia
Driving: If you’re driving, you can reach Chestertown via Route 213 or Route 301, whether you’re coming from the north or south. Flying: The nearest major airport is Baltimore/Washington International Thurgood Marshall Airport (BWI), about 70 miles away. From BWI, you can rent a car or take a shuttle service to Chestertown. Boating: Dock at the Chestertown Marina. Check slip rates here and call 410-778-3616 to book your transient slip. Parking: Once in Chestertown, parking is free and convenient. Options include on-street parking on High Street, Cross Street, and Queen Street, as well as multiple free municipal lots with time limits on Spring Street, Cannon Street, and Calvert Street. Chestertown makes the perfect addition to any Maryland Eastern Shore itinerary. Consider it as part of your day trips from Washington DC or explore more with the best day trips from Philadelphia for nature lovers.
Final Thoughts
Chestertown, Maryland, is a historic Eastern Shore town known for its brick-lined streets, colonial architecture, and scenic riverfront.
Founded in the 1700s, it offers a charming escape with over 200 independent shops, galleries, and cafes, with a variety of things to do and events.
It makes the perfect getaway or day trip if you want to discover a unique destination with tons of charm and without the crowds.
For a peaceful and luxurious retreat a few minutes from downtown Chestertown, stay at Brampton 1860.
Chestertown is compact but full of things to do!
Whether you’re planning a romantic weekend, a solo escape, or a family-friendly adventure, Chestertown offers something for everyone:
History lovers can explore colonial architecture and heritage sites
Foodies can enjoy farm-to-table dining and homemade ice cream
Browse indie boutiques for unique finds
Explore the historic waterfront or take a river cruise
Pick your own berries at Lockbriar Farms, then cool off with homemade ice cream
Support local and shop Chestertown Farmers’ Market (Saturdays, March–December) for fresh produce, flowers, and handmade goods
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