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Chestertown MD. Recommendations
33
items My recommendations for a visit to Chestertown on Maryland’s Eastern Shore, home of the annual Memorial Day weekend ‘Chestertown Tea Party’ and the annual Dickens Festival in early December.
Map
Sections
4
Outdoor Activities
Restaurants
Other Food & Drinks
Spa & salons
Outdoor Activities
Fountain ⛲️ Park is the town square of Chestertown, where events take place regularly, from music to car shows to the weekly farmers market. All visitors to Chestertown will see this park as they come through the historic district. Fountain Park, in ...
Fountain Park
The weekly farmers market on high street and in the adjoining fountain ⛲️ park and several connecting streets is open every Saturday year round. Every Saturday morning, downtown Chestertown comes alive with the sights and sounds of the Farmers Market...
Chestertown Farmers Market
This waterfront park on the Chester river is named after a long ago former mayor and has a children’s playground, a walking trail, and a large open space for activities. The annual 4th of July fireworks, the memorial weekend river raft race, and conc...
Wilmer Park
Betterton beach is a small beach at the top of Kent county a few miles north of Chestertown. The annual Betterton day & fireworks takes place in August there, with a lot of food trucks. There are other activities through the warmer months to enjo...
Betterton Beach (2025) - All You Need to Know BEFORE You Go (with Reviews)
Chestertown Historic District
The Chestertown Historic District is a National Historic Landmark in Maryland that preserves the town's colonial character as a thriving 18th-century port. Located along the Chester River, the district features a rich c...
Chestertown Historic District
Chester River Packet Company
The Chester River Packet Company offers public and private boat cruises on the scenic Chester River in Chestertown, Maryland. Operating a 65-foot, 1920s-style yacht called the River Packet, the company provides tours fro...
Chester River Packet Company
The Customs House in Chestertown, Maryland, is an 18th-century Georgian-style brick building known for its connection to colonial trade and the slave economy. Today, it is owned by Washington College and houses the C.V. Starr Center for the Study of ...
The Custom House - Chestertown
This refuge is a paradise for birdwatchers, offering miles of quiet trails through diverse habitats leading to the Chesapeake Bay. It’s a vital stopover for migratory birds.
**Tip:** Visit during spring or fall migration, and bring high-powered bin...
Eastern Neck National Wildlife Refuge
Experience maritime history firsthand by visiting the dock where the replica schooner Sultana is moored. The center often hosts educational events focused on Chesapeake Bay ecology.
**Tip:** Check their schedule for deck tours or short sailing excu...
Sultana Education Foundation
Located just south of Chestertown, CBEC features excellent boardwalk trails through marshlands and forests, showcasing local wildlife.
**Tip:** Climb the observation tower for a breathtaking 360-degree panorama of the wetlands, especially rewarding...
Chesapeake Bay Environmental Center
This park offers peaceful hiking trails winding through mature woodlands and near marsh edges. It’s a great spot for a quiet escape from town bustle.
**Tip:** Wear sturdy, water-resistant footwear, as some lower trails can be damp, and bring insect...
Radcliffe Creek canoe trail | Kent County
popular local spot offering open fields, playgrounds, and picnic areas perfect for casual recreation. It’s ideal for families looking for unstructured outdoor fun.
**Tip:** Bring kites or frisbees; the open layout is perfect for flying things on a ...
Bohemia - Maryland DNR
Famous for its vast tidal marsh landscape, this refuge is crucial for wintering waterfowl and is home to resident bald eagles.
**Tip:** Drive the 8-mile Wildlife Drive slowly, stopping frequently at designated pull-offs to use your binoculars effec...
Blackwater National Wildlife Refuge
This paved, relatively flat trail is excellent for biking, jogging, or long, leisurely walks away from vehicle traffic. It connects several small communities. **Tip:** Rent bicycles in Chestertown and ride the trail early in the morning to avoid the ...
Galena Trails and Maps - Maryland
For those seeking a slightly more rugged outdoor experience, this area offers extensive trails through diverse forests and fields suitable for hiking and nature photography.
Tip:** This area is less maintained than city parks; carry a physical map ...
Millington Wildlife Management Area
Utilize one of the public launch sites along the river to get out onto the water itself. Paddling offers a unique perspective of the shorelines
**Tip:** Rent kayaks and paddle upstream toward the smaller tributaries for a peaceful, wildlife-rich exp...
Chester River Kayak & canoe Adventures
The campus features beautiful, historic buildings surrounded by well-maintained lawns and mature trees, offering a serene atmosphere for a stroll.
**Tip:** Walk toward the back of the campus near the waterfront for quiet paths that offer lovely vie...
Washington College grounds
This small park preserves the site of an old milling operation and offers lovely views where a creek meets the Bay. It’s a great spot for a brief rest stop.
**Tip:** Look close for the historical markers detailing the area's importance to the oyster...
Parks & Recreation | Rock Hall Maryland
Restaurants
Luisa's Cucina Italiana
*Review: A beloved Chestertown staple, Luisa's serves authentic, homestyle Italian food in a cozy and welcoming setting. The portions are generous and the flavors are rich and comforting, making you feel like you're dining in ...
Luisa's Cucina Italiana
Cafe sados is located inside a refurbished historic mill and is Chestertown’s go-to for Japanese cuisine and sushi 🍱 It is a small, intimate setting, open for lunch and dinner.
Café Sado is the brain child of Chef and Founder Tony Wong. One that ha...
Cafe Sado Chestertown
Marzellas by the Bay in Betterton, MD, receives overwhelmingly positive reviews, praised for its authentic Philly-style pizza and cheesesteaks, thanks to owners who travel to the city weekly for ingredients. Patrons highlight the friendly service and...
Marzellas by the Bay | Betterton MD
**Review:A unique spot in Chestertown, Bad Alfred's combines a distillery with a brick oven pizzeria. The vibe is rustic and industrial-chic. Enjoy house-distilled spirits in creative cocktails alongside some of the best wood-fired pizza in the area....
BAD Alfred's Distilling
Watershed Alley
Watershed Alley is a refined dining restaurant in Chestertown, Maryland, that celebrates the food traditions of the Chesapeake Bay watershed. The name refers both to the Chesapeake watershed that provides its ingredients and the rest...
Watershed Alley
The Imperial
**Review:** Located in a beautifully restored historic hotel in Chestertown, The Imperial offers an upscale dining experience perfect for a special occasion. The ambiance is elegant and classic, with a menu that features sophisticated Am...
The Kitchen at the Imperial
Review:** Situated at Georgetown Yacht Basin, The Granary offers spectacular views of the Sassafras River. It provides a more upscale experience, while the adjacent Sassafras Grill is more casual. Both focus on high-quality American cuisine with an e...
The Granary
For the quintessential Maryland experience, Waterman's in Rock Hall is a must-visit. This lively, casual spot sits right on the water, offering fantastic views and even better seafood. It's the perfect place to get your hands dirty with a pile of per...
Waterman's Crab House
Harbor Shack in Rock Hall is the definition of a casual, fun, waterfront bar and grill. With live music, a sandy beach area, and a laid-back vibe, it's the spot to unwind with a cold drink and some tasty bar food after a day on the bay.
*Best Picks: ...
Harbor Shack
Other Food & Drinks
Play it again Sam is an old favorite of locals, recently moved into a much larger space to accommodate the crowd who come for coffee, treats, sandwiches, and other fare. Offers a wide variety of choices, including breakfast bagels, pastries, and glut...
Play It Again Sam
The Retriever is located in the heart of Chestertown, along with many establishments just doors away. Cocktails 🍹 Music, 🎶 oyster 🦪 nights, and meals are tops! Stop at their adjoining bottle shop for wine 🍷 and liquor 🥃 on your way out.
“Good ...
The Retriever Bar
A cornerstone of downtown Chestertown, Evergrain is a phenomenal bakery and café. The smell of fresh bread hits you at the door. It's the perfect spot for breakfast, a light lunch, or just grabbing a coffee and a world-class pastry.
*Best Picks:Almon...
Evergrain Bread Company
Sugar doodles is a recent addition to the historical district in Chestertown. This is a must-go ice cream specialty shop with out of this world ice cream 🍨 🥛 milkshakes loaded to the nines with toppings! They’re so creative!
“The menu of flavors a...
Sugar Doodles Sweet Shop
Spa & salons
Park Row Floats spa
Park Row floats is immaculate and so relaxing... a gorgeous space and lots of beautiful plants. One of the float tanks is open and one is more like an isolation capsule, but it has twinkle lights that make me feel like I am look...
Park Row Floats
Spa Angels by Tricia
a quiet, relaxing facial or massage with the place to yourself, or a fun spa get-together with friends.
Relax, Unwind & Refresh
with our AWARD winning services
Skin Care ~ Massage ~ Body Treatments ~ S...
Spa Angels by Tricia - Home