Amy's Guidebook
Food scene
This bakery is located downtown, and has excellent coffees, pastries, and breads. And some excellent (even though pre-made) sandwiches. I particularly love their Iced Chai!
37 habitants recommandent
Evergrain Bread Company
201 High StThis bakery is located downtown, and has excellent coffees, pastries, and breads. And some excellent (even though pre-made) sandwiches. I particularly love their Iced Chai!
I know it is hard to believe, but this family is making some really delicious wine - right here in Maryland! All of their wines are dry, and I can recommend all of them - whites, rose, and reds. And if you are looking for something a little more unique, definitely check out their Vermouth. It is nice to sip on either a hot or cold day! They also have a nice selection of tapas.
13 habitants recommandent
Casa Carmen Wines
312 Cannon StI know it is hard to believe, but this family is making some really delicious wine - right here in Maryland! All of their wines are dry, and I can recommend all of them - whites, rose, and reds. And if you are looking for something a little more unique, definitely check out their Vermouth. It is nice to sip on either a hot or cold day! They also have a nice selection of tapas.
This is a gorgeous space downtown. They make excellent cocktails, and he has quite the whiskey collection! Oysters are often served. While they have a limited and seasonal menu, whatever they serve is always tasty.
9 habitants recommandent
LTO
337 1/2 High StThis is a gorgeous space downtown. They make excellent cocktails, and he has quite the whiskey collection! Oysters are often served. While they have a limited and seasonal menu, whatever they serve is always tasty.
The Kitchen is a nice old hotel with a small bar and nice dining. The chef creates excellent meals and strives to keep the cost as low as he can. They also have a back patio when the weather is nice.
20 habitants recommandent
The Kitchen at the Imperial
208 High StThe Kitchen is a nice old hotel with a small bar and nice dining. The chef creates excellent meals and strives to keep the cost as low as he can. They also have a back patio when the weather is nice.
Luisa’s is known for reliably turning out absolutely delicious Italian food. If you are in the mood for Italian, you can’t go wrong in this shopping center-located restaurant.
27 habitants recommandent
Luisa's Cucina Italiana
849 Washington AveLuisa’s is known for reliably turning out absolutely delicious Italian food. If you are in the mood for Italian, you can’t go wrong in this shopping center-located restaurant.
At the far end of Chestertown, Cafe Sado is located in a gorgeously renovated old mill. The ambiance is peaceful and serene, and if you want sushi and/or Asian food, this is the place for you.
49 habitants recommandent
Cafe Sado
205 Tackle CirAt the far end of Chestertown, Cafe Sado is located in a gorgeously renovated old mill. The ambiance is peaceful and serene, and if you want sushi and/or Asian food, this is the place for you.
Phat Daddy’s is located in a shopping center between home and downtown. The owner makes delicious BBQ meats and side dishes. A very nice man, too!
7 habitants recommandent
Phat Daddy’s BBQ Shack
205 Spring AvenuePhat Daddy’s is located in a shopping center between home and downtown. The owner makes delicious BBQ meats and side dishes. A very nice man, too!
Figg's Ordinary
207 S Cross StThis gluten-free restaurant gets high reviews!
This is a coffee shop/breakfast and lunch spot right downtown. Lots of locals. I like Evergrain’s coffee and pastries better, but the made to order sandwiches here at Sam’s are quite nice!
25 habitants recommandent
Play It Again Sam
108 S Cross StThis is a coffee shop/breakfast and lunch spot right downtown. Lots of locals. I like Evergrain’s coffee and pastries better, but the made to order sandwiches here at Sam’s are quite nice!
If you don’t mind a 30 minute drive, this restaurant has an absolutely stunning outdoor bar and tables. You will feel like you have taken a vacation to the Caribbean! The elevated deck overlooks the Georgetown Marina. Beautiful!
Deep Blue Restaurant
14028 Augustine Herman HighwayIf you don’t mind a 30 minute drive, this restaurant has an absolutely stunning outdoor bar and tables. You will feel like you have taken a vacation to the Caribbean! The elevated deck overlooks the Georgetown Marina. Beautiful!
If you go to Georgetown to go to Deep Blue at the Kitty Knight House, you might also want to stop into the Fish Whistle. This is a pretty consistently good restaurant/bar.
23 habitants recommandent
Fish Whistle
100 George StreetIf you go to Georgetown to go to Deep Blue at the Kitty Knight House, you might also want to stop into the Fish Whistle. This is a pretty consistently good restaurant/bar.
OK….if you want to indulge in a traditional Maryland crab feast, Waterman’s out in Rock Hall (about a 20 minute drive) is the place to be. You can sit outdoors if the weather is nice and enjoy watching the boats come and go. Also has a view of the Bay Bridge in the distance.
33 habitants recommandent
Waterman's Crab House
21055 W Sharp StOK….if you want to indulge in a traditional Maryland crab feast, Waterman’s out in Rock Hall (about a 20 minute drive) is the place to be. You can sit outdoors if the weather is nice and enjoy watching the boats come and go. Also has a view of the Bay Bridge in the distance.
Watershed is a high end restaurant in an absolutely gorgeous interior full of local art. Nice!
13 habitants recommandent
Watershed Chestertown
337 High StreetWatershed is a high end restaurant in an absolutely gorgeous interior full of local art. Nice!
A few short miles out of town is a farm stand that sells fresh produce, flowers, and the most delicious homemade ice cream!
Lockbriar Farms
10051 Worton RdA few short miles out of town is a farm stand that sells fresh produce, flowers, and the most delicious homemade ice cream!
Visit the Farmer’s Market right downtown every Saturday morning. Guaranteed to see lots of locals roaming the closed-off streets!
14 habitants recommandent
Marylands Chestertown Farmers & Artisans Market
118 North Cross StreetVisit the Farmer’s Market right downtown every Saturday morning. Guaranteed to see lots of locals roaming the closed-off streets!
Sightseeing
If you are looking for something a little unusual, and you are here when Dave has his shop open, you should pop into this place to see some amazing old things. Dave specializes in old light fixtures, telephones, clocks, fans, etc. If you ask him some questions, he will start to talk, and you will see and learn some cool stuff!
Chestertown Electric
324 Cannon StreetIf you are looking for something a little unusual, and you are here when Dave has his shop open, you should pop into this place to see some amazing old things. Dave specializes in old light fixtures, telephones, clocks, fans, etc. If you ask him some questions, he will start to talk, and you will see and learn some cool stuff!
Washington College has some nice buildings, and is quite pretty to walk around.
16 habitants recommandent
Washington College
300 Washington AveWashington College has some nice buildings, and is quite pretty to walk around.
One of two Grand Army of the Republic (GAR) halls left in the country. You will see displays and learn a lot of history about black soldiers during the Civil War, and also about black life here in Chestertown.
Charles Sumner Post #25
206 South Queen StreetOne of two Grand Army of the Republic (GAR) halls left in the country. You will see displays and learn a lot of history about black soldiers during the Civil War, and also about black life here in Chestertown.
The Chester River Packet offers river cruises on the Chester. Take a nice sunset cruise and appreciate the farms and homes along the river. A fantastic way to get out in the water.
12 habitants recommandent
Chester River Packet Company
The Chester River Packet offers river cruises on the Chester. Take a nice sunset cruise and appreciate the farms and homes along the river. A fantastic way to get out in the water.
Shopping
Mimi's Closet
307 High StMimi’s always has a nice selection of higher end clothing and accessories.
Houston's Dockside Emporium
315 High StDockside is packed to the gills with clothing and gifts.
Located between here and downtown, Bohemia is a nice shop for casual women’s clothing, shoes, and great gifts.
Bohemia Trading Company
7400 Church Hill RdLocated between here and downtown, Bohemia is a nice shop for casual women’s clothing, shoes, and great gifts.
Empty Hangers
110 S Cross StA fairly decent-sized consignment shop carrying mostly clothes. A few home goods.
A thrift shop that has clothing and home goods. Located right next to Fountain Park downtown.
Nearly New Shop
320 High StreetA thrift shop that has clothing and home goods. Located right next to Fountain Park downtown.
Welcome Home
107 S Cross StA kitchenwares store downtown.
This store is the place to buy your high-end cheeses and charcuteries. They also have a nice, well-priced wine selection - especially roses.
22 habitants recommandent
Chester River Wine & Cheese Co.
117 S Cross StThis store is the place to buy your high-end cheeses and charcuteries. They also have a nice, well-priced wine selection - especially roses.
Something for everyone and in every price range in this gift shop downtown.
12 habitants recommandent
Twigs & Teacups
111 S Cross StSomething for everyone and in every price range in this gift shop downtown.
Art Galleries
This upstairs (above Evergrain) art gallery is curated by Carla Massoni, and she is simply wonderful. Super easy to talk to, and has a wonderful eye for putting her shows together. She also has another art space next door to Chester River Wine and Cheese. Check them both out!
9 habitants recommandent
MassoniArt Gallery
203 High StThis upstairs (above Evergrain) art gallery is curated by Carla Massoni, and she is simply wonderful. Super easy to talk to, and has a wonderful eye for putting her shows together. She also has another art space next door to Chester River Wine and Cheese. Check them both out!
RIVERARTS GALLERY
315 High StArt and artistic gifts can be found here.
While not technically an art gallery, it is a place to see some stunning art - in the form of glass. Dave and Peggy Hegland have made a name for themselves in their retirement venture. Stop by and see their beautiful glass creations. Located in the breezeway across from RiverArts.
Hegland Glass
315 High StreetWhile not technically an art gallery, it is a place to see some stunning art - in the form of glass. Dave and Peggy Hegland have made a name for themselves in their retirement venture. Stop by and see their beautiful glass creations. Located in the breezeway across from RiverArts.