Our Chestertown, Maryland bed and breakfast is located near some of the most popular towns on the Eastern Shore. Join us and enjoy a romantic getaway, great dining, shopping, outdoor adventures, & much more.

Plan ahead, you don’t want to miss these exciting events in our area or at the Brampton!

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Explore Maryland’s smallest county by car and enjoy the beauty of its rural landscape, with waterways, charming towns and animals grazing in the fields of working farms. Ask us for the Kent County Driving Tour and our own itinerary with many points of interest before heading out. Maryland’s National Scenic Byway Route 213, bisects Kent County from the northern Sassafras River border to the southern Chester River and includes Routes 20. Brampton Bed and Breakfast Inn is located on Rt. 20, the most traveled “highway” between South and North during the Revolutionary period. For detailed driving instructions, map and info click here.



This quintessential colonial village is full of historical attractions and is a great town to explore on foot. For a wonderful short movie about Chestertown, Maryland, click here. You can plan on taking a leisurely walk through one of only 6 “Royal Ports of Call” during colonial times, with the help of the Chestertown walking map. Enjoy the 2nd highest concentration of beautifully restored and maintained 18th century houses in the state of Maryland, after Annapolis. Stroll past stately homes along the Chester River. Chestertown was named the Mid-Atlantic’s most charming town by Washingtonian Magazine and is the proud home of: Washington College. Explore the campus of the 10th oldest college in the country. Founded in 1782, George Washington gave the school money, as well as his name.



Easton, about 30 miles from the inn, was named “the 8th Best Small Town in America” and is an arts and cultural center, with lots of shopping, wonderful restaurants and the Avalon Theatre.


St. Michaels

About an hour drive South of our Eastern Shore Inn in St. Michaels is the home of the Chesapeake Bay Maritime Museum. The Museum is a non-profit organization dedicated to furthering an understanding of the culture and history of the Chesapeake Bay. It is well worth a visit. During the warmer months and good weather head back from St. Michaels by taking a little detour via Bellevue and the Bellevue Oxford Ferry, believed to be the oldest continuously run ferry in the US. You won’t regret it!


Tilghman Island

Tilghman Island is a true working waterman’s village, with excellent fishing and fresh seafood everywhere. It is the home of the Rebecca T Ruark, one of the last surviving skipjacks on the Chesapeake Bay, located in Dogwood Harbor.



The capital of Maryland and a historic treasure is just an hour’s drive away. Visit the Naval Academy or take a boat ride on the Severn River. Walking tours, boat tours and bike tours are all available.

View the top things to do in Maryland, including driving around and taking in the views.