Chestertown, Maryland, is a hidden gem nestled on the banks of the Chester River. This quaint, historic town is rich in culture, heritage, and brimming with an array of things to do. Whether you're a foodie, a history buff, a nature lover, or a shopaholic, you'll discover a wealth of things to do in Chestertown. From mouth-watering local cuisine to fascinating museums, exciting outdoor adventures, and vibrant festivals, Chestertown is a destination that offers something for everyone.
There's no shortage of things to do in Chestertown. This picturesque town is not just a place to visit, but a place to explore, a place to taste, a place to experience. Known for its colonial charm, Chestertown is a treasure trove of food, events, culture, outdoors, and hidden gems waiting to be discovered. Let's dive in and explore what makes Chestertown a must-visit destination.
Food & Drink in Chestertown
When it comes to food and drink, Chestertown is a haven for food lovers. One of the top things to do in Chestertown is to visit The Kitchen at the Imperial, located on High Street. Known for its innovative menu and locally sourced ingredients, this restaurant offers an authentic taste of Chestertown’s culinary scene. For a more casual setting, head over to the Evergrain Bread Company on Cross Street. This artisanal bakery serves up freshly baked bread, pastries, and an array of sandwiches that are sure to delight your taste buds. Don't forget to wash it all down with a pint from Bad Alfred's Distilling, a local distillery that crafts its spirits with locally sourced grains. "When in Chestertown, make sure to enjoy a meal at The Kitchen at the Imperial. Their menu changes with the seasons, ensuring fresh and flavorful dishes," says local food critic, Mark Thompson.
Best Museums in Chestertown
For history buffs, visiting the local museums is one of the top things to do in Chestertown. The Chestertown Historic District is home to several 18th-century buildings, each with its unique story. The Geddes-Piper House on Church Alley offers a glimpse into the life of a wealthy 19th-century family. The Kent County Historical Society, located on High Street, houses a vast collection of artifacts that tell the story of Kent County's rich history. "Don't miss the chance to visit the Geddes-Piper House. It's like stepping back in time," advises local historian, Emily Davis.
Outdoor Adventures in Chestertown
If you're a nature lover, you'll find plenty of things to do in Chestertown. The town is surrounded by stunning landscapes, perfect for outdoor adventures. The Eastern Neck National Wildlife Refuge, a short drive from downtown Chestertown, is a paradise for birdwatchers and wildlife enthusiasts. For a leisurely stroll, head to the Wilmer Park, located on Cross Street, where you can enjoy panoramic views of the Chester River. "Take a picnic to Wilmer Park and enjoy the beautiful views of the river. It's a perfect spot to relax and unwind," recommends local resident, John Smith.
Must-See Tours & Attractions
Exploring the local attractions is among the top things to do in Chestertown. The Schooner Sultana, docked at the Chestertown Marina, offers a unique sailing experience on the Chester River. For art lovers, the Carla Massoni Gallery on High Street showcases works from local and regional artists. "The Schooner Sultana is a must-see. It's not just a boat ride, it's a journey into the past," says visitor, Laura Williams.
Festivals & Events You Can’t Miss
Chestertown is known for its vibrant festivals and events, making it one of the top things to do in Chestertown. The annual Chestertown Tea Party Festival, held in May, commemorates the town's colonial resistance against British rule. The festival features a parade, historic reenactments, and local food and crafts. Another must-visit event is the Downrigging Weekend in November, where you can see a fleet of historic tall ships. "The Chestertown Tea Party Festival is a must-see. It's a great way to experience the town's rich history and culture," says festival-goer, Sarah Johnson.
Music & Nightlife Hotspots
If you're looking for music and nightlife, there are plenty of things to do in Chestertown. The Garfield Center for the Arts, located on High Street, hosts a variety of concerts, plays, and performances throughout the year. For a more casual setting, head over to The Fish Whistle at the Chestertown Marina. This restaurant and bar offers live music, delicious food, and stunning river views. "The Garfield Center for the Arts is a gem. Their performances are top-notch and the atmosphere is intimate," says local music lover, David Miller.
Where to Shop in Chestertown
Shopping is one of the top things to do in Chestertown. The town is home to an array of unique shops and boutiques. Twigs & Teacups on Cross Street offers a variety of gifts and home décor items, while the Bookplate on Cross Street is a haven for book lovers. The Chestertown Farmers’ Market, held every Saturday, is a great place to buy fresh local produce, baked goods, and crafts. "I love shopping at Twigs & Teacups. They have the most unique gifts and home décor items," says local shopper, Lisa Brown.
Local Sports & Stadium Experiences
For sports enthusiasts, there are plenty of things to do in Chestertown. The Washington College Athletics, located on Washington Avenue, offers a variety of sports events throughout the year. From lacrosse and baseball to rowing and soccer, there's always a game to watch. "There's nothing like watching a lacrosse game at Washington College. The energy and excitement are palpable," says local sports fan, Mike Taylor.
Theatre & Performing Arts in Chestertown
Last but not least, experiencing the local performing arts scene is among the top things to do in Chestertown. The Garfield Center for the Arts offers a variety of performances, from plays and concerts to poetry readings. Another must-visit is the Prince Theatre on High Street, which hosts film screenings, concerts, and community events. "The Prince Theatre is a cultural hub. Their events are always diverse and engaging," says local theatre enthusiast, Jane Wilson.
