Chestertown, Maryland blends Colonial charm, artistic flair, and riverfront beauty. Whether you’re visiting or planning to move, explore the top things to do—from historic strolls to cultural festivals and outdoor fun.
Dining
Top Three Places for Happy Hour in Chestertown, Maryland
Raise a glass and explore the best happy hour spots in Chestertown, Maryland. From waterfront views to craft cocktails and local favorites, these top three picks serve up great vibes and even better drink specials.
Top Restaurants in Rock Hall, Maryland: A Food Lover’s Guide
Rock Hall, Maryland is more than just a charming waterfront town—it’s a hidden gem for food lovers. Whether you’re in the mood for freshly shucked oysters, a cozy weekend brunch, or takeout for your day on the water, this updated guide to Rock Hall’s top restaurants has you covered. From upscale inns to casual local favorites, these spots serve up the best flavors of the Eastern Shore.