Our Chestertown Guidebook
Food scene
Foodies from New York, we feared we'd be entering a food desert, but alas, Chestertown has plenty to offer, both regional flavors and those further afield.
Actually called The Retriever Bar & Decoy Bottle Shop, it’s a gorgeous whiskey-focused bar with a next door bottle shop open during the day. Food options include an oyster raw bar, tacos, and bar snacks. The corned beef taco is our favorite. Secret menu item: amazing donuts from nearby Stam's Lunchenette.
9 personas de la zona recomiendan
LTO
337 1/2 High StActually called The Retriever Bar & Decoy Bottle Shop, it’s a gorgeous whiskey-focused bar with a next door bottle shop open during the day. Food options include an oyster raw bar, tacos, and bar snacks. The corned beef taco is our favorite. Secret menu item: amazing donuts from nearby Stam's Lunchenette.
Refined yet still casual, the aptly named Watershed Alley has designed its food, setting, and tasteful architecture to highlight the remarkable resources of its local surroundings.
13 personas de la zona recomiendan
Watershed Chestertown
337 High StreetRefined yet still casual, the aptly named Watershed Alley has designed its food, setting, and tasteful architecture to highlight the remarkable resources of its local surroundings.
Serving their own local wines along with tapas, Casa Carmen's tasting room is created in the spirit of the traditional wine bodegas of Spain and South America—an unpretentious place to drink well, eat well, and enjoy good company.
13 personas de la zona recomiendan
Casa Carmen Wines
312 Cannon StServing their own local wines along with tapas, Casa Carmen's tasting room is created in the spirit of the traditional wine bodegas of Spain and South America—an unpretentious place to drink well, eat well, and enjoy good company.
Modern Stone Age Kitchen is a “foodery” that is a unique blend of a traditional restaurant, cafe, bakery, grocery store, and community-supported kitchen. On Friday evenings they offer fresh-baked pizza, which are 100% homemade (from sourdough crust to the cheese and sausage) using local ingredients.
Modern Stone Age Kitchen | Home of Rise By Brianna
236 Cannon StreetModern Stone Age Kitchen is a “foodery” that is a unique blend of a traditional restaurant, cafe, bakery, grocery store, and community-supported kitchen. On Friday evenings they offer fresh-baked pizza, which are 100% homemade (from sourdough crust to the cheese and sausage) using local ingredients.
A stellar cheese, wine, and specialty grocer, Chester River Wine and Cheese is the perfect place to stop in to get snacks or a whole meal to enjoy back at the guesthouse.
22 personas de la zona recomiendan
Chester River Wine & Cheese Co.
117 S Cross StA stellar cheese, wine, and specialty grocer, Chester River Wine and Cheese is the perfect place to stop in to get snacks or a whole meal to enjoy back at the guesthouse.
A classic American lunch counter and ice cream parlor, all the ice creams are fantastic and house-made. We are also personally partial to the homemade donuts, the best we've had anywhere.
8 personas de la zona recomiendan
Stam's Luncheonette
215 High StreetA classic American lunch counter and ice cream parlor, all the ice creams are fantastic and house-made. We are also personally partial to the homemade donuts, the best we've had anywhere.
While not in Chestertown, but rather a 20-minute drive to Rock Hall, Waterman's is "the place" in the area to grab crabs! Eat out on the dock overlooking the marina at sunset.
33 personas de la zona recomiendan
Waterman's Crab House
21055 W Sharp StWhile not in Chestertown, but rather a 20-minute drive to Rock Hall, Waterman's is "the place" in the area to grab crabs! Eat out on the dock overlooking the marina at sunset.
Sightseeing
Chester River Packet Company
All the art in the guest house came either from local artists or artists represented by the MassoniArt Gallery and in most cases both. With two locations, one on High St. above Evergrain Bakery and the other on Cross Street next to the Cheese and Wine Shop, you'll want to see them both. High Street will often have a single artist show or a group show around a theme, while Cross Street allows you to see a variety of represented artists all year round.
9 personas de la zona recomiendan
MassoniArt Gallery
203 High StAll the art in the guest house came either from local artists or artists represented by the MassoniArt Gallery and in most cases both. With two locations, one on High St. above Evergrain Bakery and the other on Cross Street next to the Cheese and Wine Shop, you'll want to see them both. High Street will often have a single artist show or a group show around a theme, while Cross Street allows you to see a variety of represented artists all year round.
Consejos para los viajeros
No te lo pierdas
Chestertown Tea Party Festival: May 26-28, 2023
The Chestertown Tea Party Festival is an annual event held in May to commemorate the 1774 Tea Party in Chestertown. The festival features a parade, reenactments, food vendors, live music, and family-friendly activities.
No te lo pierdas
National Music Festival: June 4-17, 2023
The National Music Festival is a two-week event held in June that brings together more than 100 professional musicians and advanced students to perform classical and contemporary music. The festival includes concerts, chamber music performances, and educational programs.
No te lo pierdas
Chestertown Jazz Festival: September 7-12, 2023
The Chestertown Jazz Festival is a three-day event held in September that features live jazz performances by local and nationally known musicians. The festival includes a main stage concert, a jazz brunch, and a jazz crawl through the town's bars and restaurants.