Chestertown, Maryland

I can't believe how many times I've been to Chestertown, Maryland--considering its on the way to nowhere. Oh wait, that's right, its unbelieveably beautiful. On Maryland's Eastern Shore (the east side of the Chesapeake Bay), Chestertown has pretty much been discovered by the locals and fully restored. Not nearly as touristy as the more famous St. Michaels farther south, Chestertown is a quiet, easily walkable town with many great shops, restaurants, and inns. So you get both relaxation and enough to do that you don't get bored. There are way too many shops to list but here are some intown hotels and restuarants to help plan your visit.

The White Swan Tavern
231 High Street
Chestertown, MD
410.778.2300
Even if you don't stay here, stop by during the day to look around and maybe tour a room or two with the staff. It'll make you want to come back.

Imperial Hotel
208 High Street
Chestertown, MD
410.778.5000
Beautiful hotel and great restaurant. Worth a try.

Blue Heron Cafe
236 Cannon Street
Chestertown, MD
410.778.0188

Brooks Tavern
410.810.0012

Crossfire Cafe
117 Cross Street
Chestertown, MD
410.778.0871