If you’re interested in a perfect Mid-Atlantic road trip, the Maryland Chesapeake Country Scenic Byway is quite the sight to see. Holding the designation of Maryland’s first nationally designated scenic byway, this beautiful road passes through the countryside, quaint towns, streams, and just about everything in between. 

Here are some of the spots you’ll want to make sure to check out along the way.


Start things off in Stevensville. It features a quintessential old-fashioned downtown, complete with historic buildings and charming streets. Head to Blackwater Distilling and Mark Cascia Vineyards to kick back and sample some whiskey or wine.

The Queen Anne’s Museum of Eastern Shore Life also takes a look into the past with recreation of a blacksmith shop, a collection of old farming tools, and other unique items like a log canoe.


Head to Waterman’s Museum in Rock Hall for a little history lesson on the area’s rich fishing history, through exhibits on oystering, crabbing, and a recreation of a traditional shanty house. Grab a nautically-themed souvenir in the gift shop on your way out.

Chesapeake Farms

Another must-stop destination is Chesapeake Farms. It’s a massive 3,300-acre expanse established in the colonial era. You can take a self-guided driving tour that explores the farm’s agricultural and wildlife practices.


At Turner’s Creek Park, you can continue looking into history on tours of the Latham House and Kent Farm Museum, which boasts slice-of-life exhibits, antiques, and artifacts. There are also 147 acres of terrain to explore, including trails and forests.

Next up

The town of Galena, a quaint small town with a little bit of something for everyone. You’ve got a walkable main street with antique shops, ice cream parlors, and boutiques, as well as The Sassafras River, where you’ll find kayaking, fishing, and sailing. The Chesapeake Wine Trail is also nearby, making for the perfect detour at the end of a long day.


Mount Harmon Plantation is a former tobacco plantation with a beautiful mansion that was built in 1730. You can take tours of the property’s main house, tobacco house, and an outdoor kitchen, which sits on the water, and boasts gorgeous views.