Chestertown Eateries and Cafés
Café's
Local eateries in and near town.
Great spot for bakery goods. They have great croissants and scones. My favorite treat is the Sun Bun. Evergrain also serves sandwiches for lunch. A good spot to get coffee and work or read.
37 locals recommend
Evergrain Bread Company
201 High StGreat spot for bakery goods. They have great croissants and scones. My favorite treat is the Sun Bun. Evergrain also serves sandwiches for lunch. A good spot to get coffee and work or read.
Good spot to have breakfast and lunch sandwiches. They have a good selection of bagels. In comparison to other places such as Evergrain, Sam's can toast/warm your sandwiches. It's mostly a college crowd, but everyone is welcomed to work/read while you have a treat.
25 locals recommend
Play It Again Sam
108 S Cross StGood spot to have breakfast and lunch sandwiches. They have a good selection of bagels. In comparison to other places such as Evergrain, Sam's can toast/warm your sandwiches. It's mostly a college crowd, but everyone is welcomed to work/read while you have a treat.
Figg's Ordinary
207 S Cross StGluten-free and healthy treats for breakfast and lunch.
I love this spot to get coffee and some delicious lunch sandwiches. This Café also has a great wine selection for purchase, as well as cute gifts. It's a great spot to explore nearby Rock Hall (approx. 20 minutes from Chestertown) There is a local marina and Easter Neck Nature Reserve
14 locals recommend
Java Rock
21309 E Sharp StI love this spot to get coffee and some delicious lunch sandwiches. This Café also has a great wine selection for purchase, as well as cute gifts. It's a great spot to explore nearby Rock Hall (approx. 20 minutes from Chestertown) There is a local marina and Easter Neck Nature Reserve
Food scene
Our local selection of restaurants
It is the trendiest restaurant we have in town. They have a great Sushi selection. Their Sushi is reasonably priced. They also serve Thai food.
49 locals recommend
Cafe Sado
205 Tackle CirIt is the trendiest restaurant we have in town. They have a great Sushi selection. Their Sushi is reasonably priced. They also serve Thai food.
Here you can get your classic Italian dishes. They also have a nice bar where you can get a drink before/during/and after your meal :)
The service is good and it is reasonably priced. Luisa's also serves traditional brick oven pizzas and your "regular" NY style pizza. They have two large seating/dinning areas. One is informal and the other side is a bit more formal.
27 locals recommend
Luisa's Cucina Italiana
849 Washington AveHere you can get your classic Italian dishes. They also have a nice bar where you can get a drink before/during/and after your meal :)
The service is good and it is reasonably priced. Luisa's also serves traditional brick oven pizzas and your "regular" NY style pizza. They have two large seating/dinning areas. One is informal and the other side is a bit more formal.
This is our newest restaurant in town serving standard Eastern Shore cuisines such as crab cakes and other seafood. They also have sandwiches, pizzas, and burgers. They have a nice bar and the views of the Chester River are very nice. This is where the Fish Whistle was formerly located before moving to nearby Georgetown, MD.
98 Cannon St
98 Cannon StreetThis is our newest restaurant in town serving standard Eastern Shore cuisines such as crab cakes and other seafood. They also have sandwiches, pizzas, and burgers. They have a nice bar and the views of the Chester River are very nice. This is where the Fish Whistle was formerly located before moving to nearby Georgetown, MD.
A typical pizza place with a large variety of pies. You can also get basic Italian food such as Chicken Parm Subs and Spaghetti and meatballs.
15 locals recommend
Procolino's Pizza
711 Washington AveA typical pizza place with a large variety of pies. You can also get basic Italian food such as Chicken Parm Subs and Spaghetti and meatballs.
I have never been to this bistro, but it is a popular restaurant for people in the area. It has a varied menu including steak, burgers, pizza, and more elaborate Eastern Shore dishes.
14 locals recommend
Uncle Charlie's Bistro
834 High StI have never been to this bistro, but it is a popular restaurant for people in the area. It has a varied menu including steak, burgers, pizza, and more elaborate Eastern Shore dishes.
This is a great place to get some tapas and some local Maryland wine from the boutique winery Casa Carmen. They are open Wednesday-Saturday.
13 locals recommend
Casa Carmen Wines
312 Cannon StThis is a great place to get some tapas and some local Maryland wine from the boutique winery Casa Carmen. They are open Wednesday-Saturday.
Stam's Luncheonette
215 High Street