The hidden gem of Maryland’s Eastern Shore is a treasure trove, providing the perfect day trip destination from many other places on the East Coast. It has a little of everything, catering to every possible interest: natural beauty, historical significance, and loads of seaside, small-town charm.
From the tranquil, wispy sand dune-studded shores of Assateague Island to countless historic destinations holding very literal national treasures and deep secrets, each day trip offers visitors a unique experience. Whether you’re a history buff, an outdoor enthusiast, or even seeking a peaceful family summer vacation, Maryland’s Eastern Shore has plenty to offer.
Immerse in The Great Outdoors at the Assateague Island National Seashore
No trip to the Eastern Shore is complete without a visit to the Assateague Island National Seashore. Known for its free-roaming wild ponies and miles of pristine sand dune-studded beaches, this barrier island offers an unforgettable experience. The seashore sits in both Maryland and Virginia, and each side offers endless adventure.
Explore the 37-plus miles of hiking and biking trails, go crabbing for those famous Maryland Blue Crabs, try surf fishing, go birdwatching or horseback riding, kayaking, camp overnight, or relax on the sandy shores. You might spot the famous wild horses grazing along the shoreline if you’re lucky!
Take a Step Back in Time in St. Michaels
St. Michaels is the epitome of a waterfront East Coast town, with beautiful scenery, charming streets lined with local restaurants and boutiques, and an atmosphere that’s both laid-back and bustling.
One of the town’s main attractions is the renowned Chesapeake Bay Maritime Museum, where visitors can immerse themselves in the area’s rich maritime history as they explore the exhibits. These include a marina full of historic boats, interactive displays, and the Hooper Strait Lighthouse (circa 1879). The museum even offers scenic river cruises aboard its 1920 boat, Winnie Estelle.
There are several other ways to explore the river outside the museum’s offerings, including narrated sunset tours and sailing charters. Prefer to do the navigating yourself? Go kayaking, stand up paddleboarding or canoeing!
This quaint seaside town also has excellent shopping, dining, wineries, and breweries. Some highlights include St. Michaels Winery and Eastern Shore Brewing, both award-winning establishments with great tasting rooms. Crab Claw is also a can’t-miss, a family-owned seafood restaurant on a dock overlooking the river.
Explore Historic Tilghman Island
Just 11 miles west of St. Michaels, separated from the mainland but connected via a drawbridge, Tilghman Island makes another beautiful day trip on Maryland’s Eastern Shore.
This scenic fishing village is known for its natural beauty, abundant boating opportunities, and some of the best seafood on the Eastern Seaboard. Particularly, Tilghman Island has long-standing roots in the oyster industry, which offers excellent dining and tour options.
Don’t leave town without checking out Rebecca T. Ruark, the oldest skipjack boat on the Chesapeake Bay! The boat was built in 1896 and earned an official National Historic Landmark designation in 2003.
Discover Kent Island’s Arts Scene (and a Hidden Beach!)
Kent Island is the biggest island in the Chesapeake Bay, the major link between Maryland’s western and eastern shores. There’s plenty to see and do here, making it one of the best options. The quaint, historic town of Stevensville is a wonderful place to start, offering a little something for every type of day-tripper.
Start in the Arts & Entertainment District, and if you can time it right, aim for a Saturday. On the first Saturday of every month from April through December, the district hosts First Saturday events, which include a local farmers’ market and open house-style tours of many of the area’s historical sites and homes. There are also plenty of antique shops, art galleries, and great cafes in the arts district, so it’s easy to fill an entire day without venturing very far.
Music enthusiasts won’t want to miss touring the Paul Reed Smith (PRS) guitar factory in town. The top-of-the-line facility is a sight to behold in its own right, but visitors can also try their hand — literally — at playing world-class guitars and witness them being made in live time. Prominent musicians like Carlos Santana and Dave Navarro of Red Hot Chili Peppers and Jane’s Addiction have their guitars made here!
One of the main reasons to visit Kent Park is its outdoor attractions. Head to the Terrapin Nature Park, with picnic areas, great hiking trails, and a “hidden” beach overlooking the Bay Bridge. Reach it by taking the park’s 3.25-mile main hiking trail.
Learn About History & the “Everglades of the North” in Cambridge
The Eastern Shore town of Cambridge, about an hour’s drive from Annapolis, has a bit of everything, making it an ideal day trip destination. The Blackwater National Wildlife Refuge, affectionately known as the “Everglades of the North,” is a great place to start, with miles of biking and hiking trails, great fishing, fascinating marshes, and unbeatable birdwatching opportunities. Stroll through the refuge on your own, or join a guided birdwatching tour.
Near the wildlife refuge is the plantation where famed abolitionist Harriet Tubman made her final escape from slavery. She would return to the area many times over the years, helping 70 others escape enslavement via the Underground Railroad. Today, you can visit the Harriet Tubman Underground Railroad National Historical Park, where you can walk and drive in the same place she once did, retracing her steps.
Uncover Maryland’s Eastern Shore
Maryland’s Eastern Shore offers an enchanting journey through a region brimming with natural beauty and delightful experiences. From the picturesque waterfront towns and charming historical sites to the idyllic landscapes and mouthwatering seafood, this coastal paradise has something for every traveler.
Any day trip through Maryland’s Eastern Shore promises to be an unforgettable adventure. Embark on a journey to this captivating region, and prepare to be swept away by the allure of it all.