15 Must-Do Activities in Cambridge, MD

A seaport community on the Eastern Shore steeped in history.

One of the oldest colonial cities in the country.

A place with a High Street called one of the most beautiful streets in America by James Michener when writing his novel, Chesapeake.

There is only one place that can claim all this and more: Cambridge, MD!

And DRB Homes is here. One of the East Coast’s premier builders, DRB Homes brings decades of award-winning excellence to this established and dynamic location.

Whether you are looking for an open concept townhome full of top notch finishes and features like those found at Pintail Landing, or prefer a single family home with wooded and creek views like those coming soon at The Tides at River Marsh, DRB Homes is ready to welcome you to Cambridge.

But what can you expect to experience living here? Here are our top 15 must-do activities in Cambridge, MD.

1. Visit the Harriet Tubman Underground Railroad Visitor Center

Born into slavery right here in Dorchester County, Harriet Tubman escaped to her freedom and then continued to rescue others through the Underground Railroad, work with the Union Army as a scout and spy, and even fight for women’s suffrage. Get ready to experience her world and explore her life and legacy in the 17-acre Harriet Tubman Underground Railroad State Park and Visitor Center. Visit exhibits, a research library, a museum store, and more, as you learn about this American hero’s contributions to helping the lives of others.

2. Explore the Blackwater National Wildlife Refuge

Just 12 miles south of Cambridge, and adjacent to the Harriet Tubman Underground Railroad State Park and Visitor Center, is the Blackwater National Wildlife Refuge. Enjoy over 5 miles of hiking trails and 17 miles of paddling trails spread out across over 20,000 acres of protected land. This naturally rich area is home to Canada geese, bald eagles, Delmarva peninsula fox squirrels, and a whole host of other indigenous flora and fauna. One visit is all it takes to see why the Nature Conservancy has called Blackwater National Wildlife Refuge one of the “Last Great Places.”

3. Stroll Along the Cambridge Main Street

Since 2003, Cambridge has officially been a Maryland Main Street community, revitalizing downtown with new businesses, historic street lights, and beautiful streetscapes. This means your trip downtown will let you explore local shops & restaurants, cafés & wine bars, art galleries & antique stores, historic buildings & museums, and even a seasonal farmers market (more below).

4. Tour the Richardson Maritime Museum

Celebrating and chronicling Cambridge’s 300 years of maritime history, the Richardson Maritime Museum is ready to introduce you to the area’s culture and the craftsmen who created it. While the main museum is currently only open upon request as it undergoes a renovation, the museum’s Ruark Boatworks is open three days a week and for special events. Admission is free, but donations are, of course, accepted and vital to the survival of this amazing destination.

5. Enjoy the Cambridge Lighthouse Museum

Though the replica of the Choptank River Lighthouse is relatively new, the original and what the replica represents date back hundreds of years. Now, head to Pier A at Long Wharf Park (see below), enter the 6-sided screw-pile lighthouse, and enjoy beautiful Choptank River vistas. Plus, there’s a small museum inside that showcases the original lighthouse’s history and importance for the whole area.

6. Visit Long Wharf Park

Long Wharf Park is a fantastic place to soak up waterfront views, have lunch on the picnic tables, and watch the boats come in and out of the Cambridge Marina. You can also fish here (no license required) and visit the skipjack Nathan of Dorchester. This type of sailing ship was used for over 100 years to collect oysters from the Chesapeake Bay, and now it offers summer public sails where you can listen to stories and history as you dredge for oysters.

7. Discover the Dorchester County Historical Society

The Dorchester County Historical Society is a local gem in preserving and displaying the area’s history in detail. Explore exhibits on the original Native Americans who lived here, colonial history, famous Dorchester residents, and more. Peruse the vast library at the museum and even attend a Heritage Tea! The Dorchester County Historical Society is a place to constantly learn, through various classes and workshops throughout the year.

8. Experience the Annual Taste of Cambridge

For 16 years, the Taste of Cambridge has been delighting the tastebuds of everyone in the community. Bringing together restaurants and chefs, this is the event your mouth doesn’t want you to miss! With different categories each year, you’ll be able to sample the best of the best—and your ticket will also allow you to cast a vote for your favorite dishes. Add live music, a market, and kids zone, and you have a stomach-filling day like no other.

9. Take a Boat Tour on the Choptank River

Having a view of the Choptank River is great, but actually being on the water is even better. There are many cruise options that will take you up and down this scenic and important waterway. From smaller and more barebones boats to large paddle-driven riverboats with luxurious feasts, you’ll travel the river, spy plenty of local wildlife, and feel even more of a connection to Cambridge.

10. Visit the Cambridge Farmers Market

From April through November, enjoy the best local produce that Cambridge has to offer at the annual Cambridge Farmers Market. You’re sure to find something special and/or delicious in this collection of Dorchester County and Eastern Shore farmers, crafters, and food vendors. And all this right in Long Wharf Park!

11. Explore Sailwinds Park

Sailwinds Park is a wonderful place for the whole family to enjoy nature. There’s a 1-mile long boardwalk where you (and your four-legged family members) can stroll and admire the beautiful scenery. A garden, beach area, fountain, and playground also await you, as does the Visitor Center. This iconic and award-winning building commemorates the area’s maritime history with a sail billowing up over 100 feet!

12. Discover Spocott Windmill and Village

The Spocott Windmill is a reconstruction of a 19^th-century windmill that was destroyed in a blizzard in 1888. Starting in the early 1970s, other historic buildings have been moved near the windmill to create a small village. Tour a colonial cottage, the original Castle Haven Schoolhouse, a blacksmith shop, a doctor’s office, and a museum and gift shop. It really is a step back in time!

13. Attend the Cambridge Arts and Entertainment District

Beating as the heart of Downtown, the Cambridge Arts and Entertainment district is where you head for art galleries & studios, live music & theatrical performances, and the Dorchester Center for the Arts (see below). You’ll also be able to enjoy some traditional Chesapeake arts, such as folk art and decoy carving.

14. Visit the Dorchester Center for the Arts

Dedicated to creating “high-quality, engaging programming in the visual, literary, and performing arts,” the Dorchester Center for the Arts is your one-stop address to visit the entire Cambridge creative community. Exhibits, events, workshops, and classes provide even more connection between Cambridge and the arts. 

15. Relax at the Bill Burton Fishing Pier State Park

Once known as The Choptank Fishing Pier, the Bill Burton Fishing Pier State Park is a wonderful place to experience the natural beauty of Cambridge. It sits on either side of the Choptank River in both Talbot and Dorchester counties, with trails, piers, and even a walkway to Sailwinds Park. Though the Talbot Pier is currently closed, the Dorchester Pier will allow fishing for perch, striped bass, sea trout, and catfish, among others. There are even fun events that take place throughout the year to make this park even more special!

Must-Do Activities near DRB Homes Communities in Cambridge, MD  

Cambridge, MD, is a vibrant town that’s rich with history, nature, and community. From exploring the Chesapeake’s scenic landscapes to immersing yourself in the town’s heritage sites and thriving local arts, Cambridge is a place that invites you to make lasting memories.

The dream of making Cambridge your home can become a reality with DRB Homes. We’ve thoughtfully designed two distinguished communities here: Pintail Landing and The Tides at River Marsh. With superior homes in prime neighborhoods, both offer the location you adore and the first class amenities you desire. DRB Homes is ready to help you find your forever place on the Eastern Shore!