Skilled boaters will compete in the Hoopers Island Waterman’s Rodeo Sept. 7
Dorchester County is rich in history, stories, natural beauty, small-town charm, and fun. Even better, some of the choicest experiences here won’t cost you a red cent. From heritage festivals to art showcases, boat races to concerts, September is filled with opportunities to enjoy the Heart of the Eastern Shore for free. Here are just a few of them.
Hoopers Island Waterman’s Rodeo
Sunday, Sept. 7 | 11 a.m.–5 p.m.
P.L. Jones Marina and Boatyard, 2560 Old House Point Rd., Fishing Creek
There’s nothing quite like the excitement of a boat docking contest—and Hoopers Island has one of the best. Watch skilled watermen and youth competitors alike back their boats into a slip, hooping four lines onto poles with speed and precision. Events include solo, team, and youth categories, culminating in a grand finale where all competitors go head-to-head for the fastest time. It’s a day full of maritime tradition and family fun.
Info: 410-397-3631
“Tubman’s First Escape” Walk & Concert
Sunday, Sept. 14 | Starts at 10 a.m.
Harrisville Road, followed by Emily’s Produce
Step into history with a narrated walk commemorating Harriet Tubman’s first attempts to escape to freedom in 1849. The guided tour takes place along Harrisville Road, near the place of her birth. Afterward, head to Emily’s Produce for a live concert by David B. Cole and Mainstreet Blues, a powerful way to honor Tubman’s journey while enjoying music in the heart of Dorchester.
RSVP here.
IRONMAN Maryland Triathlon
Saturday, Sept. 20 | All day
Gerry Boyle Park, Cambridge, and throughout Dorchester County
Cheer on athletes from around the world as they take on the ultimate test of endurance. The day begins with a sunrise swim in the Choptank River, followed by a bike course that winds through the scenic Blackwater National Wildlife Refuge. The final leg brings runners through the streets of downtown Cambridge, where thousands of supporters line the route to celebrate every stride toward the finish line. Whether you’re watching from Gerry Boyle Park or cheering in town, the energy of “Crabby Nation” is unforgettable.
Get more information here.
Choptank Heritage Skipjack Race
Saturday, Sept. 27 | 9 a.m.–12 p.m.
Long Wharf Park, Cambridge
Celebrate Dorchester’s rich maritime heritage at the annual Skipjack Race, organized by the Dorchester Skipjack Committee and the Skipjack Nathan. The day begins with a Parade of Boats at 9 a.m., followed by the race at 10 a.m. as these traditional oyster dredging vessels compete in a spectacular show on the Choptank River. With free admission, it’s a can’t-miss event steeped in Chesapeake tradition.
Get more information here.
Dorchester Center for the Arts Showcase
Sunday, Sept. 28 | 12-5 p.m.
Downtown Cambridge Arts & Entertainment District
For nearly 50 years, the Dorchester Center for the Arts has celebrated the creative spirit of the community, and this showcase is the centerpiece. Downtown Cambridge transforms into a lively street festival featuring art vendors, food, live music, dance, and maritime-inspired fun. This year brings the return of the popular chalk walk and plenty of family-friendly activities. Rain or shine, it’s one of the county’s signature cultural events.
“Harriet: A Taste of Freedom” Art Exhibition
Thursdays–Saturdays, 12-3 p.m. | Through September
Harriet Tubman Freedom Center for Cultural & Educational Advancement, 3030 Center Dr., Cambridge
Experience the legacy of Harriet Tubman through the eyes of more than 40 regional artists. This special exhibition showcases creative interpretations of Tubman’s courage, leadership, and fight for freedom. With free admission, it’s a unique opportunity to engage with both history and contemporary art.
Info: 866-227-9375 or go here.
From festivals to history walks, boat races to art, September in Dorchester County is packed with free ways to connect with the area’s culture, heritage, and community spirit. Whether you’re drawn by the water, the arts, or the story of Harriet Tubman, there’s something for everyone to enjoy. . . without spending a dime.
Write a Letter to the Editor on this Article
We encourage readers to offer their point of view on this article by submitting the following form. Editing is sometimes necessary and is done at the discretion of the editorial staff.