Islands, Towns and Charming Villages Near Chestertown

DAY ONE

Morning

Enjoy and early breakfast and head off to Easton, the colonial capitol of The Eastern Shore. Visit the historical district with over 40 restored buildings. 

Next, visit quaint St. Michaels. The marina is beautiful and attracts over 20,000 pleasure crafts a year. 

For lunch we recommend the very casual "Crab Claw" overlooking the water. This traditional crab house serves the famous crustaceans on paper tablecloths. It’s not fine dining. For a more discriminating culinary experience we recommend the Bistro.

Afternoon

If you are interested in Maritime History, visit Chesapeake Bay Maritime Museum featuring the largest collection of Chesapeake Bay watercraft in existence (over 75 boats).

If time allows, detour to Tilghman’s Island for greater seafaring atmosphere.

Drive back through St. Michaels to Bellevue and take the oldest ferry in the US across the Tred Avon River to Oxford. It is gorgeous.

Explore Oxford’s pristine waterfront location and take in the sunset views over the river before heading to Easton for a fabulous Italian meal at Scossa before heading back to the Brampton Inn.

DAY TWO

Morning

Breakfast at the Inn and drive across the Chesapeake Bay to visit historic Annapolis, about 1 hour away. Situated at the convergence of the Chesapeake Bay and Severn River, this beautiful port is also Maryland’s capitol.

We recommend parking at the garage on Duke of Gloucester Street.

Tour the Naval Academy. This is a National Historic Site and spread out over 300 acres.

Afternoon

Lunch at one of the many downtown eateries.

Walk to the end of the dock and take a boat tour on the Severn River. This is a great way to see one of America’s great harbors.

Wander the City Dock and Marina, a yachting club with hundreds of crafts of all sizes.

Before heading back you might consider eating at an Annapolis, Maryland icon; Cantler's waterfront restaurant and crab house that has been serving the area's freshest seafood to watermen, boaters, and land lovers alike for 3 decades.  If you prefer to get home before dark we highly recommend Brooks Tavern in Chestertown before returning to the inn. Brooks is less than a mile from the inn and one of our and our guests favorite restaurants.

DAY THREE

After another delectable breakfast grab your camera, pick up a Brampton Picnic Lunch and head to Adkins Arboretum. Walk around this marvelous 400-acre native garden and preserve dedicated to promoting the appreciation and conservation of the region’s native plants. More than four miles of paths along streams, through meadows and native plant gardens and under the shade of a rich bottomland forest attract nature lovers, gardeners, students and birders. You may borrow the inns binoculars.

Later in the afternoon get back to the inn and enjoy a good book, lemonade and homemade cookies or blueberry cobbler on the front porch. If you are in the mood for more seafood consider the Blue Heron Cafe or the Fish Whistle in Chestertown, or the Inn at Osprey Point or the Waterman's Crabhouse for dinner.