Things To Do
Watershed Alley
Our favorite spot for an elevated dining experience featuring seasonal American cuisine, handcrafted cocktails, and a warm, inviting atmosphere.
Crow Vineyard & Winery
BAD Alfred's Distilling
Evergrain Bread Company
Fresh artisan breads, pastries, sweet treats, and handcrafted coffee drinks.
Luisa's Cucina Italiana
Play It Again Sam
Fresh coffee, breakfast sandwiches, deli favorites, and refreshing smoothies.
The Kitchen at the Imperial
Modern Stone Age Kitchen
Historic Downtown Chestertown
Wilmer Park
Explore the Chester River by Kayak or Paddleboard (Rentals Available).
Washington College
The tenth-oldest college in the nation.
Schooner Sultana
The boat will take sail from 11am to 1pm on Sep 12th.
Chester River Walk
Self-Guided Tours
Downtown Chestertown Boutiques
MassoniArt Gallery
Chestertown Farmers Market
EVERY SATURDAY · 8AM-12PM · OPEN YEAR ROUND
Blue Bird Tavern
A casual, no-frills tavern that's been a favorite among locals for years.
Eastern Neck National Wildlife Refuge
If you're a nature lover and don't mind a short drive, you'll find several easy trails, peaceful marshes, waterfront views, and plenty of opportunities to spot bald eagles and other wildlife.