Chesapeake Charm: Settling Down in Chestertown, MD

For those considering a move to Chestertown, there’s a lot to love about this quaint riverside community. The town has a population of just over 5,000 residents, offering a close-knit, community-oriented environment where neighbors know each other and local businesses are supported with pride. While it exudes a small-town atmosphere, Chestertown is by no means isolated. It’s within a 90-minute drive to major metropolitan areas like Baltimore and Philadelphia, making it feasible for occasional city excursions or even daily commuting.

Downtown Chestertown reflects the town’s colonial past with 18th century homes and storefronts housing boutique shops, coffee houses, and restaurants. The town’s Main Street program highlights its popular attractions and makes preservation efforts for the town’s historical downtown. Keep an eye out for events and other opportunities to get out into the community!

Economically, Chestertown offers a mix of opportunities spanning education, healthcare, agriculture, and local commerce. The town also encourages entrepreneurship, with an impressive number of residents operating their own small businesses, boutiques, art galleries, and eateries. Moreover, the town’s location along the Chester River means there’s potential for businesses related to boating, fishing, and tourism.

Education is also a significant part of the Chestertown tapestry. Washington College, one of the nation’s oldest liberal arts colleges, calls Chestertown home. From lectures and arts to sports events, the college plays a pivotal role in the community’s life. See what makes Chestertown such an enticing spot for students and locals!

Explore Our Kent County Attractions

In a town that holds arts in high regard, the Garfield Center for the Arts stands tall as its cultural epicenter. Housed in a beautifully restored building, this venue is a hub of creativity and entertainment. Throughout the year, its stage comes alive with gripping plays, soul-stirring music performances, thought-provoking film screenings, and community-centric events. Whether you’re in the mood for a classic drama, a contemporary concert, or a local festival, the Garfield Center promises enriching experiences that resonate with the artistic pulse of Chestertown. Also located in the heart of town lies the Chestertown RiverArts. More than just a gallery, it’s a celebration of creativity and talent, presenting an array of artworks from talented local artists. Beyond its exhibitions, RiverArts plays a pivotal role in nurturing the artistic spirit of Chestertown through its myriad of workshops, classes, and special events, making it a cornerstone of the town’s thriving arts scene.

You can dive deep into Chestertown’s maritime legacy with the Sultana Education Foundation. It offers an unparalleled experience, allowing visitors to set sail aboard the Sultana, a meticulously crafted replica of an 18th-century British schooner. As the sails catch the wind and the Chester River flows beneath, passengers are transported back in time, getting a tangible feel of the maritime adventures and challenges of centuries past. This immersive journey is not just about the thrill of sailing; it’s a lesson in history, ecology, and the rich heritage of the region.

Outdoor enthusiasts will appreciate the area’s natural beauty, with opportunities for boating, kayaking, and bird watching. Located along the Chester River, Wilmer Park is perfect for picnics, leisurely water activities, and simply enjoying the waterfront views. It also hosts several of the town’s events and festivals, making it a community gathering spot. Here are a few other local opportunities for some sun and sand.

Bay Beaches Near Chestertown 

• Tolchester Beach (15 minutes)
• Betterton Beach (20 minutes)
• Ferry Park (20 minutes)
• Conquest Beach (35 minutes)

Rehoboth, Delaware, is 1 hour 40 minutes from Chestertown, MD—making for an easy and convenient day trip to larger beaches and boardwalks.

Chestertown Tea Party by David Clow lic CC BY-NC-ND 2.0 DEED

Chestertown Community Events: Get Involved in The Fun

There’s plenty to do in and around Chestertown year-round, from music and arts festivals to maritime events. The town is known for its annual events, like the Chestertown Tea Party Festival, which commemorates the town’s colonial resistance to British rule. Each May, residents don 18th-century costumes and reenact the province’s defiant stand against British tea taxes that preceded the Boston Tea Party. Besides theatrical reenactments along the Chester River, enjoy tea tastings, arts and crafts vendors, historic tours, and kids’ activities. The weekend-long festival reminds all of Chestertown’s pivotal role in America’s march to independence.

Each fall, Chestertown’s harbor comes alive with the sights and sounds of the Sultana Downrigging Festival. Visitors can board majestic schooners docked along the Chester River for deck tours during this celebration. Highlights include tall ship sail races sending vessels gliding gracefully across the river to the cheers of spectators onshore. On land, enjoy maritime crafts, sea shanties, children’s activities, and a lively festival atmosphere in Chestertown’s waterfront parks. The Downrigging Weekend allows locals and visitors alike to admire these historic tall ships while learning about Chestertown’s long connection to the Chesapeake Bay.

Culture Events

Accomplished musicians from around the country gather in Chestertown each summer as part of the prestigious National Music Festival. For three weeks, concerts featuring symphonies, choirs, bands, and soloists take place at venues throughout Washington College. Students also attend intensive training programs with festival faculty during this esteemed event. From classical and baroque to jazz and opera, Chestertown music lovers can take in dazzling free and ticketed performances by some of the best emerging and seasoned artists. The festival demonstrates why Chestertown deserves its reputation as an arts hub on Maryland’s eastern shore.

Jazz music fills the streets during the Chestertown Jazz Festival each September as regional and local musicians provide free concerts held at venues throughout downtown. On stages indoors and out, attendees can soak in smooth jazz, upbeat funk, soulful blues, and more from morning to night. Food vendors, crafts, and an open-air market complement the eclectic mix of rhythms showcasing Chestertown’s thriving music culture.