Chestertown Historic House Tour - Chestertown, Maryland

Join the Historical Society of Kent County for the very special  Chestertown Historic House Tour. Spend a delightful afternoon strolling the streets of this charming colonial river port which was designated as one of the National Trust for Historic Preservation 2007 Dozen Distinctive Destinations.

Rock Hall, Maryland

Tiny Rock Hall on the edge of the Chesapeake Bay is just east of more famous, historic Chestertown. This quaint fishing village combines small town ambiance with a bustling marina and is the perfect place to enjoy the water in a lazy way. Contact the Visitors Center for more information.

 

The Sailing Emporium

21144 Green Lane

Rock Hall, Maryland

410.778.1342

Dockside Cafe

21906 Chesapeake Avenue

Rock Hall, Maryland

410.639.2478

Osprey Point

20786 Rock Hall Avenue

Rock Hall, Maryland

410.639.2194

America’s Past Antiques

21260 Rock Hall Avenue

Rock Hall, Maryland

410.639.7344

 

Fishbone’s Antiques

21326 Sharp Street

Rock Hall, Maryland

410.708.3232

 

Rock Hall Gallery

3761 Main Street

Rock Hall, Maryland

410.639.2494

Textures Gallery

6202 Rock Hall Road

Rock Hall, Maryland

410.639.7211

 

Bay Leaf Gourmet

5757 Main Street

Rock Hall, Maryland

410.639.2700

Durding’s Store
5742 Main Street
Rock Hall, Maryland
410.778.7957

Frank B. Rhodes - Chestertown, Maryland

Frank B. Rhodes
535 Morgnec Rd
Chestertown, MD
410.778.3993

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