Celebrate Spring and Summer: Must-Attend Events in Kent County, MD

Kent County, MD, bursts with life during spring and summer, offering a packed calendar of festivals and events that highlight the area’s history, culture, and community spirit.

Art lovers won’t want to miss Paint the Town, Chestertown’s annual plein air festival, where artists capture the town’s beauty in real time, culminating in an exciting gallery exhibition and sale.

The season begins in May with the Galena Dogwood Festival, a cherished celebration of small-town charm. This family-friendly event features live music, artisan vendors, a parade, and delicious food, making it the perfect way to welcome warmer weather.

Later in May, Chestertown hosts the iconic Tea Party Festival, a tribute to its colonial history and rebellious spirit. The weekend is filled with historical reenactments, parades, a 5K and 10-mile run, local craft vendors, and the famous tossing of tea into the Chester River—a highlight for visitors of all ages.

As summer takes hold, 4th of July celebrations light up Kent County with dazzling fireworks and patriotic festivities. Whether you’re on the shores of Rock Hall or the streets of Chestertown, the holiday offers plenty of family fun.

In August, Chestertown’s Legacy Day takes center stage, honoring African American heritage with live music, dancing, and historical exhibits. The event brings the community together in a vibrant celebration of culture and history.

The summer wraps up with Rock Hall’s legendary Pirates and Wenches Weekend, an event that transforms the waterfront town into a pirate paradise. Visitors of all ages can enjoy costume contests, a decorated dinghy flotilla, live music, and plenty of nautical fun.

From history buffs to families and adventure-seekers, Kent County’s spring and summer events offer something for everyone. Plan your visit and experience the heart of this charming region through its lively festivals, welcoming communities, and unforgettable celebrations. To learn more please visit kentcounty.com/annualevents.