Chestertown (Maryland)

One of the most popular and high-end restaurants in town. Many locals and tourists find it to have the best food in Chestertown. The fully restored bar is a great setting for drinks before sitting down to your meal. There is an extensive wine list and the menu is filled with a variety of choices using fresh, regional ingredients. The restaurant offers seating outside during the Spring, Summer, and Fall seasons in the private courtyard.

The best Italian food in town. Cozy atmosphere and refined but not too formal.

The towns only coffee shop offering fresh brewed coffee, tea, delicious espresso drinks, sandwiches all day long, homemade pastries, bottled beer and hand selected wine for sale by the case, bottle or glass if seated. You're likely to be in line next to some Washington College students, local business owners, professors or the regulars around town. On a hot day or if you are in need of a pick-me up the signature frozen drink, The Alaskan, is a tasty espresso/chocolate fusion and the most popular. Free WIFI to customers and outdoor seating in a small side courtyard.

Swanky downtown joint open after hours as a bar. Serves great oysters and has an impressive collection of drinks, including from local breweries and vineyards.

Bed and breakfast on an 1860 luxury estate set on 35 landscaped acres. Pet Friendly rooms available. There are stand-alone cottages as well as rooms within the manor house. In addition to breakfast, the inn provides tea, cookies, and a small dessert or appetizer for tea-time at 4-5.

Comfortable accommodations for families, couples, business travellers, etc. Amenities include and indoor swimming pool, fitness center and complimentary continental breakfast.

This bed and breakfast is ideal for secluded getaways to the Chesapeake Bay area. Far from any highway or large towns, our inn will relax you with the sounds of nature, the aura of yesteryear, and the comforts of modern society.