Cozy cafes in Chestertown, Maryland

Cafe Sado is a charming eatery located at 870 High Street in Chestertown, Maryland. This cozy restaurant offers a diverse menu of delicious dishes, ranging from hearty breakfast options to savory lunch and dinner selections.

Happy Chicken - Bakery & Catering is a delightful establishment located at 215 Scheeler Road in Chestertown, Maryland.

The White Swan Tavern is a charming historic inn located at 231 High Street in Chestertown, Maryland. This cozy lodging establishment offers a unique and memorable stay for guests visiting the United States.

The Retriever Bar & The Decoy Bottle Shop is a unique establishment located at 337 1/2 High Street in Chestertown, Maryland. This hybrid venue offers a cozy and inviting bar atmosphere where patrons can enjoy a wide selection of drinks and cocktails.

Howard's Tavern is a cozy and inviting bar located at 6520 Church Hill Road in Chestertown, Maryland. Known for its friendly atmosphere, delicious drinks, and tasty pub fare, this neighborhood spot is the perfect place to unwind after a long day.

The Shanty Beach Bar is a charming seaside establishment located at 21085 Tolchester Beach Road in Chestertown, Maryland.

Procolino's Pizza, also known as Proc's, is a beloved pizza joint located at 711 Washington Avenue in Chestertown, Maryland. This cozy restaurant offers a wide variety of delicious pizzas made with fresh ingredients and flavorful toppings.

Evergrain Bread Company is a charming bakery located at 201 High Street in Chestertown, Maryland, United States. Known for their delicious freshly baked breads, pastries, and other delectable treats, this cozy store is a must-visit for food lovers.

Watershed Alley is a charming restaurant located at 337 High Street in Chestertown, Maryland. This institution offers a unique dining experience with a focus on locally sourced ingredients and seasonal menus.

The FREEZE is a popular food institution located at 717 Washington Avenue in Chestertown, Maryland. This cozy restaurant offers a variety of delicious frozen treats and comfort foods, making it a favorite spot for locals and visitors alike.

Uncle Charlie's Bistro is a cozy and inviting restaurant located at 834 High Street in Chestertown, Maryland. Our bistro offers a warm and welcoming atmosphere where guests can enjoy delicious and freshly prepared meals.

Blue Bird Tavern is a cozy and inviting bar located at 512 Washington Avenue in Chestertown, Maryland. With its charming atmosphere and friendly staff, it is the perfect spot to unwind and enjoy a cold drink with friends.

Play It Again Sam is a cozy cafe and restaurant located at 108 South Cross Street in Chestertown, Maryland. This charming establishment offers a unique dining experience with a menu that features delicious food and beverages.

China House is a popular Chinese restaurant located at 711 Washington Avenue in Chestertown, Maryland. Serving up delicious and authentic Chinese cuisine, this institution is a favorite among locals and visitors alike.

The Kitchen at the Imperial is a charming restaurant located on 208 High Street in Chestertown, Maryland. This cozy eatery offers a diverse menu featuring delicious dishes made with fresh, locally sourced ingredients.

Village House is a one-stop destination for all your home furnishing and renovation needs. Located at 103 South Cross Street in Chestertown, Maryland, this institution offers a wide range of furniture, home goods, and contracting services.

Lockbriar & Daughter ice cream is a charming ice cream shop located at 10051 Worton Road in Chestertown, Maryland. This family-run institution offers a wide variety of delicious and creamy ice cream flavors, made with locally sourced ingredients.

510 Washington Ave. is a prestigious university located in the historic town of Chestertown, Maryland.

Shore Crabbing is a charming seafood restaurant located in Chestertown, Maryland, United States. Specializing in freshly caught crabs from the nearby shores, this institution offers a unique dining experience for seafood lovers.