Things to Do in Chestertown MD: Eastern Shore Travel Guide

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

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 water's 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. — 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

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. — 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

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 — Stroll Chestertown’s 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.

For more waterfront dining experiences, check out Dock and Dine Kent Narrows MD.

Attend Chestertown Festivals and Events

Catch a show at the Garfield Center for the Arts at the Prince Theater housed in a beautifully restored 1920s theater or plan your visit around one of the many yearly events in Chestertown like the Chestertown Jazz Festival or the Sultana Downrigging Festival each fall which is the largest annual gathering of tall ships in North America combined with bluegrass music.

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

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 — Meet the resident cats in the Cat Colloquium’s 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, 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 their local rescue efforts.

If you’re traveling with 6 people or more, make an appointment before you go. For more tips on traveling with pets, check out our cat health tips.

Visit Lockbrier Farm for Fresh Produce and Homemade Ice Cream

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 — 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

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 — Downtown Chestertown’s 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

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 — 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.

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

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

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

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. — The award winning crab cake at The Kitchen at Imperial – a must-try when visiting Maryland’s 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

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

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 — 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.

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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

Modern Stone Age Kitchen (236 Cannon St, Chestertown, MD 21620) founded by food anthropologist and former Washington College professor Dr. Bill Schindler and author of “Eat Like a Human: Nourishing Foods and Ancient Ways of Cooking to Revolutionize Your Health,” this bakery, cafe and espresso bar open for breakfast and lunch is a one-of-a-kind edible destination.

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

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.

Inside Marleys Cottage at Brampton 1860 with king bed, cozy furnishings, red accent wall, fireplace, and French doors opening to a private patio — Inside Marley’s 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.

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: — Brampton 1860’s 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.

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 — Curl up with a book in Brampton 1860’s 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.

💡 Read our complete Brampton 1860 Review and discover Fall Fun at Brampton 1860 for seasonal activities.

Getting to Chestertown, MD

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

For more charming Eastern Shore destinations, explore Onancock, Virginia, Cape Charles, Virginia, The Oaks Waterfront Hotel, and Chincoteague.

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