10 Best Small Towns on the Chesapeake Bay
Legend has it that Cambridge is home to the most haunted street on the Eastern Shore (take a nighttime ghost walk to hear all the lore). That certainly doesn’t keep visitors away from this burgeoning tourist town with a growing main street lined with trendy spots such as RAR Brewing, a 1,500-square-foot craft beer joint built in an 80-year-old pool hall and bowling alley. Take a break from the brews for a history lesson: Cambridge is also home to the Harriet Tubman Museum & Education Center and a stop along the Underground Railroad driving tour.
Cape Charles, Virginia
Once a 19th-century railroading hub, Cape Charles has left behind its industrial past for a tourism-focused future, capitalizing on its pristine white-sand beaches, stately Victorians and prime waterfront property. Perched at the southern end of the Delmarva Peninsula, Cape Charles is an easy one-hour ride from Virginia Beach. A walkable main street houses the venerable Cape Charles Coffee House and Brown Dog Ice Cream, which serves up innovative flavors like beet and goat cheese with pistachio (it works). A short walk away, the lively Shanty restaurant lures with marina-front dining in a rustic setting.
Chesapeake City, Maryland
There are plenty of reminders of this town’s early 19th-century origins, from the restored Victorian and Colonial homes to the still-in-use Chesapeake & Delaware Canal, the third busiest shipping canal in the world. Learn about how the canal fascinatingly came to be (and is still maintained) at the C&D Canal Museum. Or, simply park yourself at Schaefer’s Canal House and watch the world go by while feasting on crab dip and calamari.
This Eastern Shore town of just over 14,000 was established with a courthouse; today, it enjoys a more laid-back existence with tree-lined streets and a walkable downtown. Get immersed in its thriving art scene, or visit the Adkins Arboretum, a 400-acre native garden and preserve. Go during the annual Waterfowl Festival, a celebration that promotes wildlife art, conservation, and Eastern Shore heritage.
Havre de Grace, Maryland
There’s a bit of kitsch to this town (it’s the duck decoy capital of the world, according to a museum that houses more than 3,000 of them), which ultimately makes it all the more charming. Perched at the northernmost tip of the Bay, Havre de Grace (named after a French seaport) is home to the oldest publicly accessible lighthouse on the Bay, a nationally ranked golf course, and a state park with 15 miles of hiking and wildlife trails.
Captain John Smith once dubbed this sleepy port town the “gem of the Eastern shore,” and it’s hard to disagree. With a population of just under 1,500, Onancock has small-town appeal with world-class amenities. A thriving arts scene showcases Bay-inspired works by nationally renowned artists and the old-timey Roseland Theatre hosts monthly screenings of international films. The food is equally as diverse: Bizzotto’s Gallery-Café dishes up fare with an Argentinian-Italian spin, the Blarney Stone Pub is a hub for all things Irish, and Mallard’s at the Wharf is a favorite for seafood and serenades from musician-chef Johnny Mo.
Rock Hall, Maryland
Like many cities on the Chesapeake, Rock Hall began as a sleepy harbor town; what’s unique is how much this town on the upper Eastern Shore has maintained that salty spirit. With 12 marinas, a yacht club, and a custom sailmaker in town, it’s truly a boaters’ paradise. Dining is kept casual, too: Harbor Shack blends seafood favorites with Mexican influences, and Dockside Café serves eclectic offerings, like its famous fruit pizza.
St. Michaels, Maryland
Founded in the 1600s as a thriving seaport, this tony town on the Eastern Shore has much to do beyond its marina (though don’t miss taking a cruise aboard historic cat-boat Selina II). Downtown boutiques offer everything from antiques to artisanal olive oil, and restaurants range from a trendy tapas bar to a casual waterfront seafood joint with 30-plus beers on tap. Chef David Clark at 208 Talbot whips up creative dishes (like baked oysters with prosciutto, pistachio, and champagne cream) in a cozy atmosphere.
This quiet town along the Rappahannock River was once known as a thriving tobacco port (the visitor’s center is housed in an old tobacco warehouse). Now, its claim to fame is a bit brinier. Urbanna plays host to Virginia’s largest oyster festival every year, drawing more than 75,000 visitors to its picturesque shores. Year-round, the Urbanna Seafood Restaurant & Raw Bar is a great spot for sampling fresh local oysters with sunset views.
Part of Southeastern Virginia’s Historic Triangle (along with Jamestown and Williamsburg), this 395-acre town hugs the York River with 18th-century houses, quaint boutiques and restaurants along its shores. Take a free trolley tour from the Riverwalk to Yorktown Battlefield National Park where America claimed its independence more than 300 years ago. Or, get a different view of the battlefield from the water aboard a 100-foot, three-masted schooner.