Things to Do in and Around Chestertown, MD


Brampton Inn is located in Chestertown, MD near some of the most popular towns on the Eastern Shore. The historic Chestertown is home to Washington College, one of the oldest universities in America. While Chestertown is full of history dating back to colonial times, our inn is close to other areas throughout Maryland that are worth exploring too. There are so many things to do in Chestertown, MD during your vacation.

Chestertown is near many other notable cities, including Annapolis which is the capital of Maryland. There is plenty to do outdoors from exploring nature’s beauty to fishing for fresh seafood in Tilghman Island. If being outdoors isn’t for you, head on over to the town of Easton where you can do some shopping while exploring the arts and culture there. Due to the great location of Brampton Inn, you will be able to find many things to do in Chestertown and the surrounding areas during your stay.

We’ve compiled all of our favorite things to do on the Eastern Shore in our complimentary Eastern Shore Vacation Guide. It’s the region’s most valuable resource for creating a no-hassle itinerary.


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.