Whether you’re in the mood for oysters or soft-shell crab, coffee or craft beer, golf or gallery hopping, here are 10 perfect little waterfront towns to escape to for the weekend. Or for a lifetime.
By Marisa Spyker
1 of 10Photo: drnadig/Getty
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.
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.
3 of 10Photo: AppalachianViews/Getty
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.
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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.
5 of 10Photo: Peter Gridley/Getty
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.
6 of 10Photo: Gately Williams
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.
7 of 10Photo: Karen L. Novak
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.
8 of 10Photo: coastalpics/Getty
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.
9 of 10Photo: Christopher Hunter Photography/Virginia Tourism Corporation
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.