Shopping
This store has something for everyone for the kids and the kid in you. Small clothing selection for woman, great kitchen items, books cards, soaps. A must see & shop store.
12 locals recommend
Twigs & Teacups
111 S Cross StThis store has something for everyone for the kids and the kid in you. Small clothing selection for woman, great kitchen items, books cards, soaps. A must see & shop store.
Walk along High Street and you will discover Bee Crafty Collectibles, a store that's loaded with charm and some really fun gift for the home and yourself this store carries a very unique selection of goods.
High Street
High StreetWalk along High Street and you will discover Bee Crafty Collectibles, a store that's loaded with charm and some really fun gift for the home and yourself this store carries a very unique selection of goods.
Chestertown has a very large Acme Supermarket, save yourself the hassle of bringing everything you need with you and shop for what you need 12 minutes away from the house
13 locals recommend
ACME Markets
711 Washington AveChestertown has a very large Acme Supermarket, save yourself the hassle of bringing everything you need with you and shop for what you need 12 minutes away from the house
Great Supermarket 12 minutes from the house, why bring all those coolers and ice ? Shop when you arrive less hassle, less to pack up in the car & more time for you to enjoy your vacation with family & friends.
10 locals recommend
Redner's Markets
2500 S Dupont HwyGreat Supermarket 12 minutes from the house, why bring all those coolers and ice ? Shop when you arrive less hassle, less to pack up in the car & more time for you to enjoy your vacation with family & friends.
We think it is one of the best Farmers Markets on the eastern shore! from 8 am to 12 noon every Saturday rain or shine, this Farmers Market has some of the best local produce, bread & pastries, farm-raised meats, and artisans around.
14 locals recommend
Marylands Chestertown Farmers & Artisans Market
118 North Cross StreetWe think it is one of the best Farmers Markets on the eastern shore! from 8 am to 12 noon every Saturday rain or shine, this Farmers Market has some of the best local produce, bread & pastries, farm-raised meats, and artisans around.
biking & walking trails
https://www.traillink.com/trail-maps/wayne-gilchrest-trail/
Sweet little town, with so much to offer. Biking on the new bike trail, kayaking in the Chester river, boat tours.
31 locals recommend
Chestertown
Sweet little town, with so much to offer. Biking on the new bike trail, kayaking in the Chester river, boat tours.
located just twelve miles northwest of Chestertown Center a scenic town with few than 400 year round residents. Lying on the beach here or Fishing from the pier or just watching the sunset, great!
18 locals recommend
Betterton Beach
located just twelve miles northwest of Chestertown Center a scenic town with few than 400 year round residents. Lying on the beach here or Fishing from the pier or just watching the sunset, great!
Small beach in a small harbor settled in 1706. Small & vibrant Artistic Community. Great restaurants offering steamed crab served waterside. Fishing, boating Bird watching or hiking.
25 locals recommend
Rock Hall
Small beach in a small harbor settled in 1706. Small & vibrant Artistic Community. Great restaurants offering steamed crab served waterside. Fishing, boating Bird watching or hiking.
BAD Alfred's Distilling
323 High StFood scene
Figg's Ordinary
207 S Cross StLuisa's Cucina Italiana
849 Washington AveCasa Carmen Wine House on Cannon Street is open from Wed- Sat.
Serving wine & tapas, the Wine House is created inthe sprit of the traditional wine bodgas of Spain & South America.
13 locals recommend
Casa Carmen Wines
312 Cannon StCasa Carmen Wine House on Cannon Street is open from Wed- Sat.
Serving wine & tapas, the Wine House is created inthe sprit of the traditional wine bodgas of Spain & South America.
BAD Alfred's Distilling
323 High StCafe Sado
205 Tackle CirNot your ordinary wine & cheese shop this little gem boast, gourmet foods culinary tools & Grocery Essentials.
This shop specializes in unique, small-batch producers.
Chester River wine & cheese offers beautiful cheese boards for you & your guest to enjoy, order before your arrival & pick it up on your way to the house or after you settled in. 443 282-0220
22 locals recommend
Chester River Wine & Cheese Co.
117 S Cross StNot your ordinary wine & cheese shop this little gem boast, gourmet foods culinary tools & Grocery Essentials.
This shop specializes in unique, small-batch producers.
Chester River wine & cheese offers beautiful cheese boards for you & your guest to enjoy, order before your arrival & pick it up on your way to the house or after you settled in. 443 282-0220
Tiki Bar, Paddle Boards, Kid Friendly
jellyfish joel's
22170 Great Oak Landing RdStam's Luncheonette
215 High StreetGreat lunch spot.
Amazing ice cream combo's, Milk Shakes .
City/town information
Rock Hall