Introduction
Nestled along the banks of the Chester River, Chestertown, Maryland is a charming blend of history, culture, and natural beauty. This picturesque town, founded in 1706, is one of the oldest in the state and boasts a rich colonial heritage. As you stroll through its tree-lined streets, you'll find beautifully preserved 18th-century architecture, offering a glimpse into its storied past. Chestertown's vibrant arts scene, bustling farmers' markets, and scenic waterfront make it a captivating destination for travelers seeking an authentic Eastern Shore experience.
The town's distinctive vibe is a harmonious mix of old-world charm and modern-day allure. It’s a place where you can sip coffee in a quaint café while listening to the gentle lapping of the river, or explore art galleries that showcase the talents of local artists. Chestertown is known for its warm and welcoming community, where locals greet visitors with a smile and a story. Whether you're a history buff, a foodie, or an outdoor enthusiast, Chestertown offers something special for everyone.
Families will find plenty of engaging activities, from historical tours to riverfront picnics, while foodies can indulge in the town's burgeoning culinary scene. For adventurers, the surrounding countryside offers opportunities for hiking, kayaking, and birdwatching. Whatever your interests, Chestertown promises a memorable getaway filled with discovery and delight.
Why Visit Chestertown
Chestertown is a hidden gem on Maryland's Eastern Shore, offering a unique blend of history, culture, and natural beauty. Its historic district is a treasure trove of colonial architecture, with over 50 structures listed on the National Register of Historic Places. Walking through the town feels like stepping back in time, with cobblestone streets and charming brick facades that tell stories of centuries past. The Chestertown Historic District is a must-see for history enthusiasts seeking to immerse themselves in the town's rich heritage.
Beyond its historical allure, Chestertown is a vibrant cultural hub. The town hosts numerous events throughout the year, including the Chestertown Tea Party Festival, which commemorates a colonial protest against British rule. This lively event features reenactments, parades, and plenty of family-friendly activities. Art lovers will appreciate the RiverArts Gallery, where local artists exhibit their work, offering a glimpse into the creative spirit that thrives in this community.
Nature lovers will find plenty to explore in and around Chestertown. The Chester River offers opportunities for kayaking, sailing, and fishing, while nearby parks and nature reserves provide scenic trails for hiking and birdwatching. The town's location on the Eastern Shore makes it an ideal base for exploring the region's natural beauty, from the serene landscapes of the Eastern Neck National Wildlife Refuge to the sandy beaches of the Chesapeake Bay.
A local tip: Visit in the fall when the town is ablaze with autumn colors, and the annual Chestertown RiverArts Studio Tour showcases the best of the local art scene.
Things to Do in Chestertown
One of the best things to do in Chestertown is to explore its historic district. Begin your journey at the Kent County Courthouse, a stunning example of Georgian architecture. From there, wander down High Street, where you'll find a delightful mix of antique shops, boutiques, and galleries. Don't miss the Garfield Center for the Arts, where you can catch a live performance or participate in a community workshop.
For a taste of the local culture, visit the Chestertown Farmers' Market, held every Saturday morning. Here, the air is filled with the aroma of fresh produce, baked goods, and artisanal crafts. It's a great place to mingle with locals and sample the flavors of the region. Another highlight is the Sultana Education Foundation, which offers educational programs and sailing adventures on a replica 18th-century schooner.
Outdoor enthusiasts will find plenty of activities to enjoy. Rent a kayak from Chester River Kayak Adventures and paddle along the serene waters of the Chester River, or explore the trails at Wilmer Park, where you can enjoy a picnic with a view. For a more leisurely experience, take a scenic drive through the countryside, where you'll encounter rolling farmland and charming rural landscapes.
A local tip: Don't miss the chance to attend a concert at The Mainstay in nearby Rock Hall, where you can enjoy live music in an intimate setting.
Where to Eat and Drink in Chestertown
Chestertown's culinary scene is a delightful surprise, offering a range of dining options that cater to all tastes. For a memorable meal, head to The Kitchen at the Imperial, where you can savor dishes made with locally sourced ingredients in an elegant setting. The restaurant's seasonal menu features everything from fresh seafood to hearty steaks, and the attentive service ensures a delightful dining experience.
For a more casual bite, visit The Lemon Leaf Café, known for its cozy atmosphere and delicious comfort food. Their famous cream of crab soup is a must-try, and the café's homemade desserts are the perfect way to end your meal. If you're in the mood for something sweet, stop by Evergrain Bread Company, where the smell of freshly baked bread and pastries will draw you in.
Craft beer enthusiasts should not miss Bad Alfred's Distilling, where you can sample locally brewed beers and spirits. The distillery offers tours and tastings, providing insight into the art of craft brewing. For a relaxing evening, enjoy a glass of wine at Crow Vineyard & Winery, located just a short drive from town.
A local tip: Visit Blue Heron Café for brunch and try their famous eggs Benedict, a favorite among locals and visitors alike.
Best Places to Stay in Chestertown
Chestertown offers a range of accommodations to suit every traveler's needs, from charming bed and breakfasts to modern hotels. For a truly unique experience, stay at the White Swan Tavern, a beautifully restored inn that dates back to 1733. With its period furnishings and cozy atmosphere, the inn offers a glimpse into the town's colonial past while providing modern comforts.
If you prefer a more contemporary setting, consider The Kent Manor Inn, located on a picturesque waterfront estate. This elegant inn offers luxurious rooms and stunning views of the Chester River, making it an ideal choice for a romantic getaway. For families, the Holiday Inn Express & Suites Chestertown offers comfortable accommodations and convenient amenities, including a pool and fitness center.
For those seeking a more intimate experience, the Simply Bed & Bread provides personalized service and a warm, welcoming atmosphere. This charming bed and breakfast is known for its delicious homemade breakfasts and attentive hosts who go out of their way to make guests feel at home.
A local tip: Book your stay during the annual Chestertown Jazz Festival for a chance to enjoy world-class music in a beautiful setting.
Tips for Visiting Chestertown
When planning your visit to Chestertown, consider timing your trip around one of the town's many festivals or events. The Chestertown Tea Party Festival in May and the Downrigging Weekend in October are particularly popular, offering unique experiences that showcase the town's history and maritime heritage. These events provide an opportunity to engage with the local community and enjoy a festive atmosphere.
Transportation in Chestertown is convenient, with most attractions located within walking distance of each other. However, renting a bike from Bicycle Connection is a great way to explore the town and its scenic surroundings at your own pace. The town's flat terrain and picturesque landscapes make it ideal for cycling.
When dining out, it's a good idea to make reservations, especially on weekends and during peak tourist seasons. Many of the top restaurants in Chestertown, Maryland, are popular with both locals and visitors, so securing a table in advance ensures you won't miss out on a delicious meal.
A local tip: Take a sunset stroll along the Chester River Walk, where you can enjoy breathtaking views of the river and the town's historic skyline.
