Where to Eat

Either before or after you sail on the Tall Ships, there’s a variety of great places to grab a bite to eat in Chestertown.

On the Waterfront (down by the Tall Ships)

Fish Whistle Restaurant & Festival Tent Located just feet from the Tall Ships, the Fish Whistle Restaurant offers premiere waterfront dining for lunch and dinner as well as drinks and bar food late into the evening.    For those seeking something quicker or more casual, look for the large festival tent in the parking lot behind the Fish Whistle for takeout food, beer, and additional picnic-style seating.  The Fish Whistle Festival Tent will be open Friday from 4:00-10:00pm, Saturday from 9:00am to 6:00pm, and Sunday from 9:00am -4:00pm.

The River Packet / Foot of High Street Chestertown’s own River Packet, a 65-foot reproduction of a 1920’s yacht, will be serving food right down on the waterfront with a perfect view of the Tall Ships.   Click here for more information on the River Packet at Downrigging Weekend.

Downtown (walking distance from the Tall Ships)

7-Eleven / 212 Maple Avenue – Slurpee’s, corndogs, pizza, snacks and soda – open 24 hours.

Blue Heron Café/236 Cannon StreetFeatures innovative and classic American Regional cuisines with a menu that includes fresh seafood, Maryland Crab Cakes, steaks, chops, pastas, vegetarian dishes and their famous Oyster Fritter.

Chestertown Natural Foods / 303 Cannon StreetA small, high-quality store featuring local, all-natural and organic vendors that strives to provide the best gourmet products available.

Chester River Wine & Cheese Co./117 South Cross St.  – Osteria style menu featuring domestic and imported wines, cheese, salmi, and pate served at indoor fireside tables or outside along Cannon St. Gourmet foods are available in the market, for consumption onsite, or packaged as a picnic to go.

Ellen’s Coffee Shop & Family Restaurant / 205 Spring Avenue – Breakfast fare and lunch counter items. Scrapple is available all day.

Evergrain Bread Company / 201 High StreetEuropean style bakery and coffee shop with fresh baked artisan bread and pastries. Known for baguettes and Sun Buns.

J.R.’s Past-time Pub / 337 High Street – “Fern bar” atmosphere with full food menu available from companion restaurant, Lemon Leaf Café. Bar features regional Micro-brews on tap in addition to hand crafted cocktails.

Lemon Leaf Café / 337 High Street Featuring a variety of contemporary and Eastern Shore cuisine on the lunch and dinner menu with traditional breakfast items in the morning. Known for their Cream of Crab Soup and flannel cakes.

Play it Again Sam / 108 S. Cross Street– Local hangout for espresso drinks and full service lunch. Specialties include the BLT & Avocado and Hot Roast Beef and Brie.

The Kitchen / 208 High StreetThe restaurant located at the Imperial Hotel features a revolving menu of classic and modern cuisine based on fresh local ingredients. The wine list is extensive and the staff is knowledgeable with suggestions and pairings.

Uptown (you’ll need a car)

Café Sato / 870 High Street This local favorite features a combination of sushi and Thai cuisine all served within a quirky historic grain mill. Local favorites include Sado Jumbo Roll and Thai Bouillabaisse.

Louisa’s / 849 Washington Avenue – Get a pizza to go or stay for authentic Italian Cuisine featuring local fresh ingredients all served in their lovely dining room.

O’Connor’s Pub / 844 High StreetA traditional Irish Pub in the heart of the Eastern Shore, O’Connor’s serves pints of Guinness alongside hand crafted cocktails and their traditional Irish cuisine can’t be beat. Try the Shepherd’s Pie, Bangers and Mash or Molly Milligan’s Mussels.

Plaza Tapatia / 715 Washington Avenue Plaza Tapatia proudly serves authentic Mexican cuisine with prompt, friendly service.

Procolino’s / 711 Washington Avenue – 35 Years as Chestertown’s pizza restaurant has made “Proc’s” a local institution. Offerings include pizza, pasta, gluten free pizza, subs, salads and more. They have regional favorite birch beer on tap in addition to the regular soda options and bottled beer.

Uncle Charlie’s Bistro / 834 High Street Bistro style food with an emphasis on seafood and steak, Charlie’s offers a full service meal with large portions, great service and fresh ingredients.