What to do in Chestertown

Explore Scenic Chestertown!

Chestertown, established in 1706, was once an important seaport during the colonial period and is now the county seat of Kent County. Chestertown is not a town that history forgot; instead, it is a town that history gratefully remembers. Proud of their colonial past, residents have restored many of the Georgian and Federal homes built during the 18th century by wealthy merchants.

Watch as Innkeeper Beth Lavery shares the history of the Inn and her favorite tips for enjoying scenic Chestertown.

Watershed Restaurant entrance in Chestertown MD

Aerial view of Chestertown MD showing downtown Inn location

The White Swan is one of many historic buildings that makes up the architecturally interesting downtown! Be sure to grab the walking tour guide at the front desk.

See the Our History page for more information about the restoration and history of The White Swan.

Shopping in Chestertown

Chestertown’s walkable downtown is filled with locally owned shops and galleries, perfect for a leisurely afternoon stroll. You’ll find everything from handcrafted jewelry and artwork to books, home décor, and artisan gifts.

Guest favorites within walking distance:

Walnut and Wool Stylish home goods and accessories

Twigs & Teacups Eclectic gifts, stationery, and kitchenware

The Bookplate Beloved independent bookstore with local authors and signings

Mimi’s Closet Stylish and well made clothing, shoes, jewelry & accessories and excellent personal service!

RiverArts Gallery & Gift Shop Rotating art exhibits of local artists and unique gifts

And of course, the famous Chestertown Farmers Market ( Year-round on Saturdays)

Tip: Visit midweek to enjoy quieter shops and more personalized service.

Dining & Local Flavors in Chestertown

Chestertown’s food scene blends local flavor with small-town charm. Best of all, most restaurants are just a few minutes’ walk from the inn. Here are few staff and guest favorites:

The Watershed Alley

The Retriever Bar & The Decoy Bottle Shop

Stam’s Luncheonette

Modern Stone Age Kitchen

Chester River Wine & Cheese

The Kitchen at the Imperial

Luisa’s Cucina Italiana

Bad Alfred’s Brew Pub, Distillery, and Wood-Fired Pizza

Play It Again Sam

Cafe Sado

Not sure where to eat? Ask us for our top recommendations and/or reservations!

Entrance to Watershed Restaurant in Chestertown MD

Outdoor & Waterfront Activities

The quiet pace of the Eastern Shore makes it a wonderful retreat, whether you are a boating enthusiast, a cyclist eager to enjoy some of the best bike riding in the region, a kayaker looking to explore the area’s many waterways, or a lover of college sports.

Popular activities in Chestertown include:

Cruise the Chester on the Chester River Packet: a 1920’s style river boat

Enjoy a two-hour sail on the 1768 schooner Sultana

Get close to nature on a guided kayak tour of the Captain John Smith Chesapeake National Historic Trail featuring pristine wetlands full of plants, animals and scenic views

Take an intimate sail with Blue Crab Charter’s 43 foot Morgan center cockpit sailboat

Catch some college sports and stroll the historic waterfront campus of Washington College

Take a scenic drive to Eastern Neck National Wildlife Refuge. Located on the Atlantic Flyway, this beloved wildlife refuge is a birdwatcher’s paradise!

Bike or walk Chestertown’s Wayne Gilchrest Rail Trail

Taste local wine with a vineyard tour at Crow Vineyard & Winery

Arriving in Chestertown by Boat?

Dock at the new Chestertown Marina. Let us know and we can transport you back and forth to your slip in our golf cart!

Chestertown Events & Festivals

In Chestertown, we love to celebrate our rich maritime heritage, thriving arts community, and vibrant downtown life. Every season there is a reason to visit Chestertown!

Signature annual events in Chestertown:

Chestertown Farmers Market (Every Saturday, year-round) Local produce, meats, prepared food, flowers, and handmade goods right outside our front door.
Chestertown Tea Party Festival (Memorial Day Weekend) Historic reenactments, parades, and colonial fun downtown. The parade comes right down High St. in front of the Swan!
National Music Festival (June) Attend rehearsals and performances of music students.
Chestertown Jazz Festival (September) National and regional jazz performances along the waterfront.
First Fridays (Monthly, year-round) Downtown shops and galleries stay open late with live music and refreshments.
Dickens of a Christmas (December) The first weekend in December, Chestertown transforms into a Victorian holiday market complete with carolers, vendors, horse-drawn carriage rides, bonfires in the street and live music.

Top tip: Staying midweek or off-season can mean smaller crowds and easier access to popular experiences.