Guidebook for the Eastern Shore
Arts & Culture
Historic Theater for plays, music and much, much, more
13 locals recommend
Garfield Center for the Arts at the Prince Theatre
210 High StHistoric Theater for plays, music and much, much, more
Mainstay
5753 N Main StMusic venue in Rock Hall
RIVERARTS GALLERY
315 High StArt Gallery and so much more!
Shopping
Bayside Foods Inc
21309 Rock Hall AveGrocery Store in Rock Hall
Redner's Markets
2500 S Dupont HwyGrocery Store in Washington Plaza
ACME Markets
711 Washington AveGrocery Store in Kent Plaza in Chestertown
This is where you buy crabs, fresh fish and seafood. GPS it - it's near Rock Hall.
Read all Chester River Seafood in an article from Edible Delmarva
https://edibledelmarva.ediblecommunities.com/shop/chester-river-seafood
9 locals recommend
Chester River Seafood
4954 Ashley RdThis is where you buy crabs, fresh fish and seafood. GPS it - it's near Rock Hall.
Read all Chester River Seafood in an article from Edible Delmarva
https://edibledelmarva.ediblecommunities.com/shop/chester-river-seafood
Serving our community with natural foods, the best produce, plants, and fresh subs from our Deli!
7 locals recommend
Fresh Start Food and Garden
21318 E Sharp StServing our community with natural foods, the best produce, plants, and fresh subs from our Deli!
Parks & Nature
Cute little seashell-shaped beach on the Bay - lovely views of the sunset over the water.
9 locals recommend
Ferry Park
Cute little seashell-shaped beach on the Bay - lovely views of the sunset over the water.
Swimming pool, Rec Center, Basketball Courts, Track -- the works!
7 locals recommend
Kent County Community Center (and Pool)
11041 Worton RdSwimming pool, Rec Center, Basketball Courts, Track -- the works!
Sightseeing
"The Jewel of the Chesapeake" Lovely, sandy beach, with a bathhouse about 20 miles from Tolchester. Great restaurant overlooking the beach called Barbara's on the Bay
18 locals recommend
Betterton Beach
"The Jewel of the Chesapeake" Lovely, sandy beach, with a bathhouse about 20 miles from Tolchester. Great restaurant overlooking the beach called Barbara's on the Bay
A full-scale reproduction of a vessel that sailed the Chesapeake in the years before the American Revolution, SULTANA now voyages as the “Schoolship of the Chesapeake.”
17 locals recommend
Sultana Education Foundation
200 S Cross StA full-scale reproduction of a vessel that sailed the Chesapeake in the years before the American Revolution, SULTANA now voyages as the “Schoolship of the Chesapeake.”
Rock Hall
Little town nearby with a beach, boating and restaurants
Historic, picturesque church - built in 1620. Famously the resting place of Tallulah Bankhead.
St Paul's Kent
7579 Sandy Bottom RdHistoric, picturesque church - built in 1620. Famously the resting place of Tallulah Bankhead.
Historic, college town on the Chester River. 20 minutes from Tolchester
31 locals recommend
Chestertown
Historic, college town on the Chester River. 20 minutes from Tolchester
Eastern Neck National Wildlife Refuge
1730 Eastern Neck Island RdBeautiful, natural adventures
Ohio Community Beach - Chesapeak Bay beach - good for looking for rocks, sea glass, and views of the Bay, Boats. Also a place to launch a boat or fish.
Ohio Avenue
Ohio AvenueOhio Community Beach - Chesapeak Bay beach - good for looking for rocks, sea glass, and views of the Bay, Boats. Also a place to launch a boat or fish.
Entertainment & Activities
Group, individual or guided environmental tours and Bay wildlife observation for paddlers of all ages.
Chester River Kayak Adventures
5758 N Main StGroup, individual or guided environmental tours and Bay wildlife observation for paddlers of all ages.
Haven Charters
20846 Rock Hall AveGreat boating on the Chesapeake
Chesapeake Movies
21 Washington SquareMovies in Chestertown
Cat Colloquium
215 High StCats, Cats, Cats!
Drinks & Nightlife
Chateau Bu-De, LLC Bohemia Manor Farm
237 Bohemia Manor Farm LnGorgeous setting - superb winery.
Crow Vineyard & Winery
12441 Vansant Corner RdAmazing winery.
Food scene
Cafe Sado
205 Tackle CirAsian Cuisine and Sushi
Luisa's Cucina Italiana
849 Washington AveGreat Italian Food and Wood Fire Pizza
98 Cannon Riverfront Grille
98 Cannon StRestaurant on the Chester River
Waterman's Crab House
21055 W Sharp StCRAB SHACK!
Harbor Shack
20895 Bayside AveLively restaurant in Rock Hall
Evergrain Bread Company
201 High StCoffee, bread, cafe.
Java Rock
21309 E Sharp StCafe in Rock Hall
Uncle Charlie's Bistro
834 High StGood, comfort food. Fireplace in winter.
Play It Again Sam
108 S Cross StCoffee Shop and lunch counter
Marylands Chestertown Farmers & Artisans Market
118 North Cross StreetSaturdays from 8am - noon.
Now named The Retriever: Great bar in Chestertown, featuring oysters, plus a bottle shop.
9 locals recommend
LTO
337 1/2 High StNow named The Retriever: Great bar in Chestertown, featuring oysters, plus a bottle shop.
Marzella's By The Bay LLC
3 Howell Point RoadPizza and more in Betterton
Watershed Alley on High Street in historic downtown Chestertown
Chesapeake Bay watershed is their source.
Refined dining on Maryland’s Eastern Shore, with clean & simple, regional food.
A Watershed Moment in Chestertown
article from Edible Delmarva
https://edibledelmarva.ediblecommunities.com/eat/watershed-moment-chestertown
13 locals recommend
Watershed Chestertown
337 High StreetWatershed Alley on High Street in historic downtown Chestertown
Chesapeake Bay watershed is their source.
Refined dining on Maryland’s Eastern Shore, with clean & simple, regional food.
A Watershed Moment in Chestertown
article from Edible Delmarva
https://edibledelmarva.ediblecommunities.com/eat/watershed-moment-chestertown
Modern Stone Age Kitchen
236 Cannon Streetscratch-made, artisan food
https://modernstoneagekitchen.com/
Waterfront Dinning on the beautiful Sassafras!
Delicious Menu, Weekly Specials & Full-Service Bar.
Outdoor Waterfront Dining & Carry Out Available
23 locals recommend
Fish Whistle
100 George StreetWaterfront Dinning on the beautiful Sassafras!
Delicious Menu, Weekly Specials & Full-Service Bar.
Outdoor Waterfront Dining & Carry Out Available
Ford's Seafood in Rock Hall, Maryland offers genuine Eastern Shore dishes in a comfortable family setting. Family owned and operated, we have been serving our community fresh and local seafood dishes since 1995. Specializing in steamed Maryland Blue Crabs (often caught same day by our local waterman).
7 locals recommend
Ford's Seafood
21459 Rock Hall AvenueFord's Seafood in Rock Hall, Maryland offers genuine Eastern Shore dishes in a comfortable family setting. Family owned and operated, we have been serving our community fresh and local seafood dishes since 1995. Specializing in steamed Maryland Blue Crabs (often caught same day by our local waterman).
Healthy, Fresh, Salads, Soups and Smoothies.
Quick, Easy, Healthy, To Go (near the circle in Chestertown)
Karma Cleanse Cafe
860 High StreetHealthy, Fresh, Salads, Soups and Smoothies.
Quick, Easy, Healthy, To Go (near the circle in Chestertown)
A mixture of Austrian and Eastern Shore Cuisine located in the heart of Rock Hall MD.
HOURS:
OPEN: MONDAY-SATURDAY: 4PM-9:00PM CLOSED SUNDAYS (Temporary Hours due to COVID-19 Reopening Phases, please call to verify hours)
410-639-2000
10 locals recommend
Bay Wolf Restaurant
21270 Rock Hall AveA mixture of Austrian and Eastern Shore Cuisine located in the heart of Rock Hall MD.
HOURS:
OPEN: MONDAY-SATURDAY: 4PM-9:00PM CLOSED SUNDAYS (Temporary Hours due to COVID-19 Reopening Phases, please call to verify hours)
410-639-2000
Figg's Ordinary offers gluten and refined sugar free snacks, baked goods, breakfast, and lunch in Chestertown, MD.
https://www.figgsordinary.com/
10 locals recommend
Figg's Ordinary
207 S Cross StFigg's Ordinary offers gluten and refined sugar free snacks, baked goods, breakfast, and lunch in Chestertown, MD.
https://www.figgsordinary.com/