11 Charming Small Towns You Need to Explore On Your Next Chesapeake Bay Vacation

Walk down the picturesque cobblestone streets of Chestertown. Photograph by Pat Blackley/Alamy.

Does your idea of exploring the bay involve window shopping, walking cobblestone streets, and soaking up the local vibe in a coffee shop or waterfront bar? Here are the best places to point your car.


Once home to canneries and seafood-packing houses, Cambridge now claims an up-and-coming main street with restaurants and galleries, not to mention the riverfront Hyatt Regency Chesapeake Bay, a good base from which to explore Blackwater National Wildlife Refuge, about ten miles south. Local tip: RAR Brewing (504 Poplar St.; 443-225-5664) spikes beers with interesting flavors such as butternut squash.

Cape Charles, Virginia

The handsome Victorians in this town at the tip of the Delmarva Peninsula are a reminder of its railroading heyday. Shops and restaurants line the main drag, Mason Avenue, which ends at one of the nicer beaches on the bay. Local tip: Start the day with the “famous French toast” at Cape Charles Coffee House (241 Mason Ave.; 757-331-1880), in a 1910 former bank with Art Deco chandeliers.

Chesapeake City

The historic district has enough antiques shops and locally owned boutiques to while away an afternoon, but the real draw is watching boat traffic along the Chesapeake & Delaware Canal. Book a room at one of the waterfront bed-and-breakfasts for a front-row seat. Local tip: For live music and margaritas, grab a stool on the dock of Schaefer’s Canal House (208 Bank St.; 410-885-7200).


Home to Washington College, this town’s re-stored 18th- and 19th-century rowhouses and cobblestone streets abut the picturesque Chester River. Local tip: Evergrain Bread Company (201–203 High St.; 410-778-3333) has some of the flakiest croissants this side of the Seine.


The Talbot County seat has a thriving arts community and a walkable downtown dotted with some of the best restaurants on the Eastern Shore. Local tip: Grab breakfast or lunch at Hill’s Drug (30 E. Dover St.; 410-822-2666), an old-fashioned pharmacy/luncheonette with stuffed sandwiches and ice-cream treats.

Irvington, Virginia

Only 500 people or so call Irvington home, but its upscale boutiques and places to stay—the Tides Inn and Hope and Glory Inn—lend this idyllic burg a sophisticated feel. Local tip: Settle in with a New York Times and an espresso at the Local (4337 Irvington Rd.; 804-438-9356), a place where locals actually do congregate.

Onancock, Virginia

It’s been called the St. Michaels of Virginia’s Eastern Shore for its urbane restaurants, inns, and galleries, but this port town still has plenty of down-home charm. Local tip: Hit the Saturday farmers market (corner of Market and Ames Sts.) for finds including steamed crabs and jewelry crafted from sea glass.


Oxford has resisted the development and glitz of neighboring Easton and St. Michaels, instead exuding a quiet charm. Take a stroll—with views of the Tred Avon River—or a jaunt aboard the Oxford-Bellevue Ferry, operating since 1683. Local tip: Browse the beautiful boats, and the museum, at Cutts & Case Shipyard (306 Tilghman St.; 410-226-5416), nationally known for restoring vintage vessels.

Rock Hall

Lifelong watermen and weekend sailors alike head to Rock Hall for its nautical flavor, complete with marinas, a small beach, and waterfront crabhouses. Local tip: Summer means root-beer floats at Durding’s Store (5742 N. Main St.; 410-778-7957), an old-time ice-cream parlor in a building that dates to the 1870s.

St. Michaels

Oysters and shipbuilding may have made St. Michaels, but these days the tourists who flock to the tony boutiques and restaurants keep its economy hopping. Local tip:St. Michaels looks even prettier from the Miles River. Book a tour with Captain Iris Clarke on the Selina II (410-726-9400), a sleek cat-boat from the Gatsby era; $65 to $85 per person.

Urbanna, Virginia

Though known for its oyster festival every November, this former tobacco port—with a boating scene along Urbanna Creek and 18th-century buildings—is far prettier when the weather’s warmer and an extra 50,000 to 75,000 people aren’t around. Local tip: Slurp oysters on the half shell year-round at the waterfront Urbanna Seafood & Raw Bar (453 Johnsons Dr.; 804-758-8588).

This article appears in our July 2016 issue of Washingtonian.