You don’t need to spend a bundle to enjoy the beauty, history, and fun that Dorchester County has to offer on Maryland’s Eastern Shore. We’ve rounded up the Top 10 things to do here that don’t require you to open your wallet at all!

Choptank River Lighthouse, Cambridge, MD - Photo by Jill Jasuta1. See the View at the Choptank River Lighthouse

Admire this six-sided screwpile lighthouse from a distance – set against the Choptank River with its red roof vibrant against a blue sky or even a cloudy sky. Stroll along Pier A at the Municipal Yacht Basin with its mixture of workboats and recreational boats, and take the steps up to the deck of the lighthouse for a lovely view of the river and waterfront. Head inside for a small museum with stories of the original version of this replica lighthouse and local maritime heritage. Open daily, 9:30am-5pm for self-guided tours. Docents are usually on hand on weekends to answer any questions.

Elliotts Island Road at Sunrise - Dorchester County, MD - Photo by Jill Jasuta2. Explore World’s End and Beyond

Fill up or charge up the car and meander the back roads of Dorchester County – you’ll feel like you’ve stepped into another world. Head to Hoopers Island, home to traditional waterman’s villages nearly surrounded by water. Make the long trek to Elliotts Island, where the marshland stretches around you with not much else. Or explore the far reaches of Southern Dorchester County (“Down Below,” as the locals call it) where you’ll find nary a Wawa, coffee shop, or gas station. And yes, you can get to “World’s End via Route 336 (Golden Hill Road) where a causeway and small bridge is known as “World’s End Turn” as it passes over a creek of the same name.

Waterman's Rodeo - Hoopers Island, MD - Photo by Coty Jones3. Go to a Free Festival

Enjoy the sights, sounds, and tastes of one of Dorchester County’s events with free admission, including:
Groove City Culture Fest (Aug. 19) – Music, vendors, performances organized by the Groove City Black Heritage & Culture Group
Hoopers Island Waterman’s Rodeo (Sept. 10) – Watch boat captains of all ages show off their boat docking skills.
Choptank Heritage Skipjack Race (Sept. 23) – Chesapeake icons take to the river in a picturesque race of these traditional oyster dredging vessels. Organized by Dorchester County’s own Skipjack Nathan.
Dorchester Center for the Arts Showcase (Sept. 24) – Arts festival on Dorchester County’s most historic and scenic street.
Johnny’s Tavern Bike Show (Sept. 23) – Admire bikes of all types, along with music and food.
Hurlock Fall Festival & Train Rides (Oct. 7) – Small-town festival with food, vendors, music, entertainment. Train rides require a paid ticket.
Taste of Cambridge (Oct. 7, 1-6pm) – Street fest with music, vendors, fun for kids, and optional ticketed tasting with local chefs and craft brewers and distillers.

'Ode to Watermen' Mural by Michael Rosato - Cambridge, MD4. Take the Chesapeake Mural Trail

Wander the roads of Dorchester County to take in the beauty of murals that help share stories of the area, from watermen to notable women to railroading. There’s even an audio guide where the artist of most of the murals talks about his inspiration.

5. Explore Harriet Tubman Country

Harriet Tubman Underground Railroad Visitor Center - Church Creek, MDUnderground Railroad hero Harriet Tubman was born here in Dorchester County more than 200 years ago. Take the scenic road trip known as the Harriet Tubman Underground Railroad Byway and see some of the places where she lived, toiled, and led escapes to freedom. Short on time? Stop by the homegrown, volunteer-run Harriet Tubman Museum & Educational Center  in Downtown Cambridge, or the Harriet Tubman Underground Railroad Visitor Center in Church Creek,  a partnership of the Maryland and National Park Services, with multimedia exhibits and more.

6. Reach out to Harriet Tubman

'Take My Hand' Mural of Harriet Tubman by Michael Rosato - Photo courtesy Maryland TourismFor a quick yet powerful experience of Harriet Tubman, head to these two spots where public art has become a bit of a mecca: See the “Beacon of Hope” sculpture at the Dorchester County Courthouse (206 High St., Cambridge) – a 12-foot bronze sculpture by Wesley Wofford of Tubman with her younger self that was installed in 2022.  Then walk or drive the three blocks to the Tubman Museum (424 Race St., Cambridge), where tucked away on the exterior side wall of the museum is “Take My Hand,” a mural that went viral when it was completed in 2019, and has continued to draw thousands to experience an oversize version of Tubman reaching her hand out to the viewer.

Fishing at Long Wharf, Cambridge7. Fish Without a License

Bring your own rod and reel to Long Wharf Park in Cambridge, where you can fish from land without needing to get a fishing license. Just look for the signs designating the free area at the park, located near the intersection of High and Water Streets in Cambridge.

8. Go Back in Time

With Native American roots going back more than 10,000 years and settlers arriving here in in the 1600s, Dorchester County is chock full of history. A few places to dig into the past:

  • Handsell Historic SiteOld Trinity Church - Dorchester County, MD, which shares the stories of three cultures (Native Americans, European settlers, and Black enslaved and free people) who each inhabited the land here. The grounds are open dawn to dusk, with signage, a Native American longhouse you can peek into, and an Audio Tour by cell phone (call 410-858-4173).
  • Old Trinity Church is a quaint, restored brick structure that dates back to the 1600s, set on a bucolic spot on the Church Creek. This Episcopal church is probably the oldest in continuous use in its original form. The cemetery includes the graves of three Revolutionary War heroes.
  • Spocott Windmill & Village features an English-style post windmill (the entire structure can be rotated into the wind), as well as buildings from the 1800s including a cottage, one-room schoolhouse, country store, and doctor’s office. Wander the grounds for a self-guided tour dawn to dusk daily. There are signs that share the history.
  • Dorchester County is home to several historic cemeteries, including at Christ Episcopal Church in Cambridge, Cambridge Cemetery, Old Trinity Church, and Malone’s Church. Learn more.
  • Historic High Street: Amble down this brick-cobbled street for views of houses from the 1700s and 1800s. Pick up a self-guided walking tour brochure from the Dorchester County Visitor Center for a fuller experience or listen to some of the eerie back stories by joining a Cambridge Ghost Walk.

Make it even more fun for the kids by trying the Passport Tour.

9. Row Your Boat, Kayak, or SUP

Kayaking in Dorchester County, MD - Photo courtesy Maryland TourismIf you have your own boat, you’ll find about two dozen fee-free boat ramps, as well as several soft launches for kayaks and SUPs around Dorchester County. Dorchester is the only county on the Mid-Shore that does not require permits and fees at public landings. Read more. For paddlers, there are three marked water trails at Blackwater National Wildlife Refuge,  or explore on your own. See our Dorchester Paddling Guide for suggested routes.

10. Be Inspired by Artistic Creations

3ten Creative Design & Gift Gallery - Cambridge, MDArtists of all kinds and styles call Dorchester County home. From plein air to modern abstracts, from photography to ceramics, wide-ranging work is featured at the Dorchester Center of the Arts  and Main Street Gallery  and 3ten Creative Design & Gift Gallery,  which change out their exhibits regularly. For more art, stop by Downtown Frame of Mine  and Goose Country Art & Frame.


Things to Do With Your Kids This Summer

Find plenty of family-friendly outdoor adventures, interesting hands-on experiences, and fun with kids in Dorchester County! Let the kids take the wheel of a traditional oystering boat, pick berries from the plant, glide on a stand-up paddleboard, and much more. Our 2023 Family Fun Guide is chock full of ideas.

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