When it comes to things to do in Chestertown, MD, the challenge is not finding something worthwhile. It is deciding what to do first. Founded in 1706 along the banks of the Chester River, Chestertown blends colonial charm with a vibrant arts scene, outstanding dining, and a relaxed waterfront atmosphere. Brick sidewalks lead past historic homes, independent shops, galleries, and restaurants, with the river as the backdrop. Whether you’re planning a weekend getaway or a day trip on the Eastern Shore of Maryland, Chestertown, MD, offers the perfect mix of history, culture, and small-town charm.
Part of what makes the list of things to do in Chestertown, MD, so appealing is how easily it connects visitors to the rest of the Eastern Shore of Maryland. Located in Kent County, Chestertown puts you within easy reach of waterfront villages, wildlife refuges, scenic kayak trails, and some of the best Chesapeake Bay towns on the Maryland coast. Just a short drive away, you’ll find plenty of things to do in Rock Hall, from spending a relaxing day at Rock Hall Beach to enjoying fresh seafood at some of the best restaurants in Rock Hall. Together, these neighboring towns showcase the best of the Eastern Shore experience.
After a day spent exploring the best things to do in Chestertown, MD, you’ll want a place where you can slow down and recharge. That’s exactly what you’ll find at the Inn at Huntingfield Creek, our bed and breakfast in Maryland, located less than 25 minutes from Chestertown. Set on 70 waterfront acres, our inn combines warm Chesapeake hospitality with comfortable accommodations and full country breakfasts. Whether you’re planning a romantic getaway or a weekend exploring some of the best Chesapeake Bay towns, our Eastern Shore retreat is the perfect place to call home during your visit. Book your stay today!
The Top Things to Do in Chestertown, MD
Part of what makes the best things to do in Chestertown, MD, so memorable is the setting itself. Nestled along the Chester River, Chestertown combines centuries of history with a thriving arts scene, locally owned shops, waterfront dining, and the relaxed pace that defines the Eastern Shore of Maryland. Its downtown and historic district are listed on the National Register of Historic Places, where brick sidewalks, colonial architecture, and river views create one of the most picturesque settings on the Maryland coast. Add the cultural influence of Washington College and a rich maritime heritage, and it’s easy to see why Chestertown has earned a reputation as one of the best Chesapeake Bay towns.
Here are some of the top things to do in Chestertown, MD:
- Explore the Chestertown Historic District, one of the most rewarding things to do in Chestertown, MD. Designated a National Historic Landmark District, this beautifully preserved area showcases centuries of architecture, history, and waterfront charm. As you wander along High Street and nearby side streets, you’ll discover colonial homes, historic churches, independent shops, galleries, and views of the Chester River. The district’s walkable layout makes it easy to spend an entire morning browsing and sightseeing.
- Get out on the water. Kayaking or paddleboarding on the Chester River is one of the most popular things to do in Chestertown, MD. Calm waters, shoreline views, and frequent wildlife sightings make it a great choice for visitors looking for outdoor activities on the Eastern Shore. Paddling also provides a unique perspective of Maryland’s Eastern Shore and its diverse wildlife, including osprey, herons, and bald eagles.
- Sail on the Schooner Sultana. For a truly unique Eastern Shore experience, climb aboard the Schooner Sultana, a faithful reproduction of the 1768 trading vessel. During the two-hour sail on the Chester River, passengers can help raise the sails, steer using the seven-foot tiller, and explore the crew’s quarters below deck. It’s one of the most unique things to do on the Eastern Shore, and a fascinating way to connect with the region’s maritime history. Public sails are offered seasonally, so be sure to check the schedule before your visit.
- Visit Washington College, a historic landmark founded in 1782 with the support of George Washington. The picturesque campus features beautiful architecture, green spaces, and cultural attractions that enrich the experience of visiting Chestertown, MD. History buffs and architecture enthusiasts alike will appreciate the opportunity to explore one of the nation’s oldest colleges.
- Visit Chestertown RiverArts. Chestertown’s thriving arts community is on full display at RiverArts. Visitors can browse gallery exhibits, shop for locally made artwork, explore the Clay Studio, or participate in workshops and special events throughout the year. For those interested in the creative side of the Eastern Shore of Maryland, RiverArts offers a wonderful opportunity to connect with local artists and experience the cultural character that makes Chestertown unique.
- Experience the best restaurants in Chestertown. From casual cafés and bakeries to waterfront dining and refined restaurants, Chestertown offers an impressive variety of culinary experiences for a town of its size. Many restaurants emphasize fresh seafood, local ingredients, and Eastern Shore hospitality, giving visitors an authentic taste of Maryland’s coast.
- Visit the Chestertown Farmers Market, a beloved local tradition and one of the best ways to experience the community. Open year-round every Saturday from 8 a.m. to noon, the market fills High Street with local produce, meats, seafood, baked goods, flowers, and handcrafted goods. Recognized by the American Farmland Trust as the best farmers’ market in Maryland, it offers visitors a chance to meet local farmers, artisans, and food producers while enjoying downtown Chestertown.
- Attend the Chestertown Tea Party Festival. Held each Memorial Day weekend, the Chestertown Tea Party Festival celebrates the town’s colonial heritage with reenactments, parades, live music, and family-friendly events. It is one of the signature things to do on the Eastern Shore and attracts visitors from across the region each year.
The best time to visit Chestertown depends on what you’re hoping to experience. Spring and fall bring mild temperatures and a busy calendar of festivals and community events, while summer is perfect for getting out on the Chester River. Even in the quieter winter months, the town’s shops, galleries, restaurants, and historic streets make for a rewarding getaway. No matter when you visit, you’ll find plenty of memorable things to do in Chestertown, MD, and discover why it remains one of the most charming Maryland coastal towns to explore.
The Best Bed and Breakfast in Maryland
After a day spent exploring the best things to do in Chestertown, MD, we invite you to slow down and savor a quieter side of the Eastern Shore at our Bed and Breakfast in Maryland. Here, evenings are often spent watching the sunset, strolling the grounds, or relaxing with a glass of wine and one of our homemade salted chocolate chip cookies.
When it’s time to turn in, our individually decorated guest rooms offer a comfortable retreat, with king-size beds, fine linens, and thoughtful touches. The next morning begins with a full country breakfast featuring farm-fresh ingredients and homemade favorites, served around the communal table. Whether you’re planning a romantic getaway, a weekend of exploration, or simply looking for a welcoming bed and breakfast in Maryland, we’d be delighted to share our corner of the Eastern Shore with you. Book your stay today!
