Guidebook for Chestertown
Shopping
Fabulous place for fun, whimsical gifts. Also sells clothing (love the Flax collection). NOTE: Twigs & Teacups' store is being completely transformed and is closed on Cross Street. However the owners have relocated the boutique around the corner (on High Street, near Stams' Luncheonette) until the big store is ready to reopen, later this fall.
12 locals recommend
Twigs & Teacups
111 S Cross StFabulous place for fun, whimsical gifts. Also sells clothing (love the Flax collection). NOTE: Twigs & Teacups' store is being completely transformed and is closed on Cross Street. However the owners have relocated the boutique around the corner (on High Street, near Stams' Luncheonette) until the big store is ready to reopen, later this fall.
Food Scene
Evergrain is a fantastic bakery, with a great eat-in ambiance along with cafe tables outside on the sidewalk. Terrific pastries (too good if you know what I mean), excellent coffee, good sandwiches.
37 locals recommend
Evergrain Bread Company
201 High StEvergrain is a fantastic bakery, with a great eat-in ambiance along with cafe tables outside on the sidewalk. Terrific pastries (too good if you know what I mean), excellent coffee, good sandwiches.
Fabulous food! It's hidden away, def. a locals place (behind the Subway sub shop), but go for the fried oysters, peanut butter/chocolate pie, ribs, reubens, anything). Decent wine list.
14 locals recommend
Uncle Charlie's Bistro
834 High StFabulous food! It's hidden away, def. a locals place (behind the Subway sub shop), but go for the fried oysters, peanut butter/chocolate pie, ribs, reubens, anything). Decent wine list.
Unfortunately, 98 Cannon Riverfront Grille, our only waterfront restaurant, had a fire last winter. Through summer and into fall, however, it's added a food truck scene and sells casual fare and cocktails (terrific beer list), with tables under a tent right by the Chester River, so it's a pleasant place to stop.
9 locals recommend
98 Cannon Riverfront Grille
98 Cannon StUnfortunately, 98 Cannon Riverfront Grille, our only waterfront restaurant, had a fire last winter. Through summer and into fall, however, it's added a food truck scene and sells casual fare and cocktails (terrific beer list), with tables under a tent right by the Chester River, so it's a pleasant place to stop.
Everything Else
This is a fabulous flea market, held every Wednesday morning (open until everything's sold). It's fabulous to just watch but you may also find a bargain.
Crumpton
This is a fabulous flea market, held every Wednesday morning (open until everything's sold). It's fabulous to just watch but you may also find a bargain.
Funky bayside town 20 minutes west of Chestertown, with good seafood joints, small boutiques, antique stores and art galleries, and even a beach for swimming.
25 locals recommend
Rock Hall
Funky bayside town 20 minutes west of Chestertown, with good seafood joints, small boutiques, antique stores and art galleries, and even a beach for swimming.
Massive bookstore, mostly secondhand books (you never know what you'll find) but also gorgeous Portuguese ceramics and local art.
6 locals recommend
Book Plate
112 S Cross StMassive bookstore, mostly secondhand books (you never know what you'll find) but also gorgeous Portuguese ceramics and local art.
It's one of our two big grocery stores, better for meats and flowers than Redner's. The latter is a warehouse market and is too new to show up on map but is about a block further north on Route 213.
13 locals recommend
ACME Markets
711 Washington AveIt's one of our two big grocery stores, better for meats and flowers than Redner's. The latter is a warehouse market and is too new to show up on map but is about a block further north on Route 213.
One of a handful of liquor stores, we like this one best for its terrific wine and beer selections, not to mention more upper end liquors. Decent prices.
Pip's Liquors
1 Washington SquareOne of a handful of liquor stores, we like this one best for its terrific wine and beer selections, not to mention more upper end liquors. Decent prices.
Small, but a good place for packaged goods. Nice gluten-free selection.
8 locals recommend
Chestertown Marina LLC
207 S Water StSmall, but a good place for packaged goods. Nice gluten-free selection.
Essentials
It's not cheap -- but it's a fantastic place for discerning cheese and wine lovers to pick up supplies.
22 locals recommend
Chester River Wine & Cheese Co.
117 S Cross StIt's not cheap -- but it's a fantastic place for discerning cheese and wine lovers to pick up supplies.
Arts & Culture
It's a fabulous art gallery; owner Carla Massoni has a great eye for interesting art, nice balance between shore-related & just gorgeous collectibles.
9 locals recommend
MassoniArt Gallery
203 High StIt's a fabulous art gallery; owner Carla Massoni has a great eye for interesting art, nice balance between shore-related & just gorgeous collectibles.
Entertainment & Activities
There's a terrific swimming pool (and snack bar). Admission, I believe, is $5 per person.
7 locals recommend
Kent County Community Center (and Pool)
11041 Worton RdThere's a terrific swimming pool (and snack bar). Admission, I believe, is $5 per person.