Best Things to Do in Chestertown, MD, for an Eastern Shore Getaway
Discover the Best Things to Do in Chestertown, MD
When it comes to finding the best things to do in Chestertown, MD, visitors quickly discover that this historic waterfront town offers far more than a typical day trip. Founded in 1706 along the Chester River, Chestertown combines colonial history, a thriving arts community, waterfront recreation, and exceptional dining, making it one of the best Chesapeake Bay towns to explore on Maryland’s Eastern Shore.
The heart of town is the Chestertown Historic District, a National Historic Landmark District filled with preserved colonial architecture, brick sidewalks, independent boutiques, galleries, and river views. Strolling through downtown is one of the most rewarding things to do on the Eastern Shore, offering a glimpse into centuries of Maryland history while enjoying the town’s welcoming atmosphere.
Outdoor enthusiasts will find plenty of opportunities to experience the Chester River. Kayaking and paddleboarding are popular ways to explore the shoreline, where visitors often spot osprey, herons, and bald eagles. For a deeper connection to the area’s maritime heritage, a sail aboard the Schooner Sultana offers an unforgettable experience on the water.
Visitors can also explore Washington College, one of the nation’s oldest colleges, founded in 1782 with support from George Washington. The picturesque campus adds another layer of history and culture to any visit. Nearby, Chestertown RiverArts showcases the town’s creative spirit through gallery exhibits, artist studios, workshops, and community events.
Food lovers will appreciate the variety of restaurants, bakeries, and cafés throughout town. Many feature fresh seafood and locally sourced ingredients that reflect the flavors of the Eastern Shore, Maryland region. A visit to the award-winning Chestertown Farmers Market is another excellent way to experience local culture while shopping for produce, seafood, baked goods, and artisan products.
Stay at a Bed and Breakfast in Maryland
After a day spent exploring the best things to do in Chestertown, MD, retreat to the Inn at Huntingfield Creek, a welcoming bed and breakfast in Maryland located less than 25 minutes from downtown. Situated on 70 waterfront acres, the property offers comfortable accommodations, peaceful surroundings, and authentic Chesapeake hospitality.
Guests can relax with sunset views, stroll the grounds, or unwind with homemade salted chocolate chip cookies before settling into thoughtfully appointed guest rooms featuring king-size beds and fine linens. Each morning begins with a full country breakfast prepared with fresh ingredients and homemade favorites. Whether you’re planning a romantic escape or a best coast getaway exploring Maryland coastal towns, the Inn at Huntingfield Creek provides the perfect home base. Book your stay today.