Jim and Tracy have lived in Kent County for almost 30 years. They know the local restaurants extremely well and can make a recommendation for the best place to go based on your preferences. Below is a list of restaurants they often recommend to guests.

We’ve broken this list down by town to make it easier to find a restaurant in the area you’d like to explore:

Chestertown Historic District Restaurants

  • 98 Cannon - Riverfront dining, lunch, brunch, and dinner
  • The Kitchen at the Imperial - Historic Hotel, lunch, brunch, and dinner
  • Evergrain - Bakery, coffee, breakfast, and lunch
  • Stam's - Ice Cream, breakfast, and lunch
  • Play it Again Sam's - Coffee shop, breakfast and lunch
  • Figg's Ordinary - Gluten-free options, breakfast, and lunch
  • Chester River Wine and Cheese
  • Casa Carmen - Boutique winery and tapas
  • Zelda's - Speakeasy
  • Bad Alfred's - Distillery and brick oven pizza
  • The Retriever - Bar, and dining for dinner

Rock Hall Restaurants

  • The Harbor Shack - Waterfront dining, lunch, and dinner
  • The Waterman's Crab House - Waterfront dining, lunch, and dinner
  • The Wheelhouse - Waterview dining, lunch, and dinner
  • The Inn at Osprey - Fine dining, dinner
  • Baywolf - Austrian and regional cuisine, lunch and dinner
  • Passages - Waterfront dining, lunch, and dinner
  • Get the Scoop - Ice Cream
  • Ford's Seafood - Seafood retail, breakfast, lunch, and dinner
  • Java Rock - Coffee shop, sweets, and lunch
  • Sweet Cheeks - Candy shop
  • Anchor and Plow - Pizza and sandwiches, dinner
  • Muskrat Alley Cafe - Gift shop, breakfast
  • Chester River Seafood - Wholesale, retail, crabs, and more

Chestertown Restaurants Outside the Historic District

  • Uncle Charlie's Bistro - Lunch and dinner
  • O'Connor's Pub - Irish bar, and dining for dinner
  • Cafe Sado - In an old Mill, Sushi and Sashimi, lunch, and dinner
  • Germaine's - Soups and Sandwiches, carryout
  • Procolino's - Italian, pizza by the slice, lunch, and dinner
  • Luisa's Cucina - Italian, pizza, lunch, and dinner
  • Blue Bird - Local bar, pool tables, lunch, and dinner
  • Ellen's Coffee Shop - Diner, breakfast, and lunch
  • Beverly's Family Restaurant - diner, breakfast, and lunch

Restaurants in Georgetown, Kennedyville, Galena, Millington, and Betterton

  • Fish Whistle at the Granary - Waterfront dining, lunch, brunch, and dinner
  • Molly's - Sporting goods, home cooking, breakfast, lunch, and dinner
  • The Kitty Knight House - Historic water view, brunch, lunch, and dinner
  • Twinnies - Family style, breakfast, lunch, and dinner
  • Two Trees - American, Vegetarian-friendly, lunch, and dinner
  • Barbara's on the Bay - Waterview, American contemporary, lunch, and dinner