The Eastern Shore is a great place to visit with many charming small towns.
You might learn something new or discover your new favorite day-tripping destination.
These are our picks for some of the best towns on the Eastern Shore to visit with family.
St. Michaels, MD
Quaint and peaceful, St. Michaels was the runner-up for the “Best Historic Small Town” award in USA Today’s 2025 Readers’ Choice Awards. Once an important location during the War of 1812, it’s now a relaxing place to spend some time by the shore.
One of the town’s biggest attractions is the Chesapeake Bay Marine Museum, which is celebrating its 60th anniversary in 2025. The museum also functions as an active shipyard, so visitors can see historic and working boats. Another must-see is the Classic Motor Museum, a meetup spot for vintage car collectors which houses a collection of 20th century vehicles.
Boating is a popular activity for locals and tourists alike. Rent a kayak or paddleboard and take on the St. Michaels Water Trail, four designated boating trails that take paddlers around the town’s waterways.
Chincoteague Island, VA
Chincoteague Island is home to the only publicly accessible beach between Ocean City and Virginia Beach but is a quieter getaway than both of those bustling vacation towns.
It’s popular for fishing, crabbing and boating in the summer, but the island is probably best known for its wild ponies — like in Marguerite Henry’s children’s novel, “Misty of Chincoteague.” The Chincoteague Volunteer Fire Company has held an annual pony swim (from neighboring Assateague Island to Chincoteague) drawing about 40,000 visitors each July since 1925, followed by a carnival and auction of the ponies.
It also has one of the most popular wildlife refuges in the United States. If you’d like to spy a bald eagle, the Chincoteague National Wildlife Refuge has hiking, kayaking and bird watching on its 14,000 acres, with more than 400 species of birds. Looking for dolphins? Try an island boat tour.
If your eyes are set above the atmosphere, you can see space-themed exhibits at the nearby NASA Wallops Flight Facility Visitor Center — and even watch rocket launches!
Cape Charles, VA
Cape Charles has the only public beach on Virginia’s Eastern Shore that doesn’t charge an entrance or parking fee. Cape Charles Town Beach has calm, clear water with small waves, making it perfect for paddleboarding, kayaking or just going for a swim with younger family members who may not be ready for rougher ocean waves.
The town’s historic district dates back to the 1880s, leaving many preserved buildings to visit. If you’re in the mood for a concert or play, the Historic Palace Theatre, which is housed in a 1940s movie house, is an especially unique venue.
The area also has a few interesting nature parks. Savage Neck Dunes has some of the tallest sand dunes on the Eastern shore, while the Cape Charles Natural Area Preserve gives visitors a view of the surrounding forest from an elevated boardwalk.
Onancock, VA
Onancock was called “the gem of the Eastern Shore” in the 17th century, and that reputation still holds true today. The town has a rich history, apparent in museums such as the Watermen’s Heritage Museum, dedicated to the titular profession in Virginia, and the Samuel D. Outlaw Blacksmith Shop Memorial Museum, a working smithy where visitors can learn about blacksmithing and watch metalworkers in action.
The town is also ideal for art lovers. See beloved classics and original theater at The North Street Playhouse. The Eastern Shore Art League has its home base in town and often hosts exhibits and art-themed events. And the vintage Roseland Theater shows foreign films and holds an annual international film festival that brings film buffs into town.
Cambridge, MD
Cambridge is a waterfront town surrounded by the countryside. Its downtown has been lauded as one of the best in the country, and it’s a great place to spend the day shopping and eating. Explore art via Dorchester Center of the Arts, a local nonprofit supporting arts education, or learn about famed abolitionist Harriet Tubman, who was born nearby. The town is home to the Harriet Tubman Museum & Educational Center, which honors her life and legacy. The Harriet Tubman Underground Railroad Scenic Byway also passes through town and encompasses the trails that were used by former slaves on their journey to freedom.
