10 Adorable Small Towns on the Chesapeake Bay

The Chesapeake is the largest estuary in the United States, stretching about 200 miles between Havre de Grace at the head of the bay and the mouth at Cape Charles where Virginia meets the Atlantic. Its shorelines hold a string of small towns built around oysters, blue crabs, sailboats, and the tide. Annapolis is the best-known stop; the Eastern Shore communities and cape towns anchor their own corners of the bay. The ten towns below are the small-town options worth a long weekend along Chesapeake Bay.

Annapolis, Maryland

Founded in 1649 and home to the United States Naval Academy since 1845, Annapolis carries more history per block than just about any other town its size on the eastern seaboard. City Dock at the foot of Main Street has been a working harbour for over 300 years and remains the social centre of town, with sailboats off the bulkhead and restaurants lining the wharf. The Naval Academy is open for guided tours, including the chapel where the remains of John Paul Jones lie in the crypt below. Quiet Waters Park covers 340 acres on the south side of town with paved trails, a dog beach, and kayak rentals on Harness Creek. Sandy Point State Park sits at the western foot of the Bay Bridge with one of the best public swimming beaches on the bay.

St. Michaels, Maryland

St. Michaels has been known as "the town that fooled the British" since the War of 1812, when residents reportedly hung lanterns in the trees above town on the night of August 10, 1813, so that British naval cannons would overshoot their targets. The Hooper Strait Lighthouse, an 1879 screw-pile lighthouse moved here from Tangier Sound, anchors the Chesapeake Bay Maritime Museum's 18-acre waterfront campus. The museum interprets the bay through working boats, oystering exhibits, and a rotating fleet of historic vessels. Talbot Street is the main commercial drag, with a tight cluster of restaurants and a couple of breweries including the Eastern Shore Brewing taproom. The 1.3-mile St. Michaels Nature Trail follows the old railroad bed out to the edge of town.

Cape Charles, Virginia

Cape Charles sat largely empty for most of the 20th century after the railroad ferry to Norfolk shut down in 1953, which is part of why so many of its 1880s and 1890s Victorian buildings still stand today. The town has rebounded over the past two decades as a low-key beach destination on the bay side of Virginia's Eastern Shore. The public beach is one of the few stretches on the Chesapeake with calm, swimmable water and a sand bottom rather than the usual marsh and mud. Cape Charles Brewing Company occupies a former farm-equipment store on Mason Avenue and pairs its lineup with wood-fired pizzas. The Shanty, set on the working harbour, runs the local seafood spot with rockfish and crab cakes coming straight off the boats. Kiptopeke State Park, 10 minutes south, is one of the best raptor-watching sites on the eastern seaboard during autumn migration.

Kent Island, Maryland

The first English settlement in Maryland was established on Kent Island in 1631 by William Claiborne, four years before the colony's official founding at St. Mary's City. The island is now the first stretch of the Eastern Shore that drivers reach after crossing the Bay Bridge from Annapolis. The Stevensville Historic District holds the surviving 18th- and 19th-century structures, including the Cray House, an early-1800s tenant house and one of the oldest buildings on the island. The six-mile Cross Island Trail runs east-west across the island on the bed of an old railroad, connecting Terrapin Nature Park at the western edge to Kent Narrows on the east. Terrapin Park has a half-mile of sandy beach facing the Bay Bridge and good fossil-hunting along the waterline. Hemingway's restaurant on Kent Narrows is the long-running stop for crab cakes with bridge views.

Urbanna, Virginia

Urbanna was laid out in 1680 as one of twenty official tobacco ports authorised by the Virginia colonial legislature under the Cohabitation Act, and is the only one of those twenty still operating as a working port today. The Old Tobacco Warehouse, built around 1763, still stands on Virginia Street and houses the Urbanna Museum and Visitor Center. The first weekend of November brings the Urbanna Oyster Festival, the official oyster festival of the Commonwealth of Virginia, which has run annually since 1958 and packs the town with around 75,000 visitors over the two days. The town marina sits on Urbanna Creek a few miles up from where it meets the Rappahannock River, which makes it a regular stop for boaters working up and down the bay. Marshall's Drug Store on Cross Street still operates its original 1930s soda fountain.

Onancock, Virginia

The Tangier-Onancock ferry departs the Onancock wharf each summer morning and is the main public-passenger access to Tangier Island, the most isolated working watermen's community on the bay. Onancock itself dates to 1680 and has held on to a substantial Eastern Shore main street, with Ker Place at the head of Market Street as the architectural anchor. Built in 1799 by Scottish merchant John Shepherd Ker, the house runs as the headquarters of the Eastern Shore of Virginia Historical Society. Mallards at the Wharf operates as the waterfront seafood spot directly off the marina. North Street Playhouse keeps a year-round community-theatre schedule out of a converted general store. Onancock holds an unusually dense cluster of working art galleries and studios for a town its size, packed into a few blocks of the downtown.

Solomons Island, Maryland

The Calvert Marine Museum sits where the Patuxent River meets the bay and runs as one of the most complete maritime museums on the Chesapeake. The relocated Drum Point Lighthouse, an 1883 hexagonal screw-pile design, sits at the museum as its centrepiece. The museum's palaeontology hall covers the Miocene-era shark teeth and whale bones that wash out of the nearby Calvert Cliffs by the bagful. Calvert Cliffs State Park, 25 minutes north, is the public access point for that 30-mile stretch of fossil-rich cliffs along the bay. The Solomons Island Riverwalk follows the harbour edge and connects the museum to the Tiki Bar, a Solomons institution that opens each April with a season-launch party so chaotic that it briefly trends on local news every year. Stoney's Kingfishers handles the local seafood end of the dining scene with hard-shell crabs from the dock outside.

Easton, Maryland

Easton was incorporated in 1788 and served as the unofficial colonial capital of Maryland's Eastern Shore. It still holds the regional courthouse, the Talbot County Free Library, and the Avalon Theatre, a restored 1921 movie palace that books a heavy schedule of touring music. The Academy Art Museum on South Street keeps regional and contemporary exhibits in a renovated 18th-century schoolhouse. The Waterfowl Festival, running every November since 1971, fills the downtown with sporting-art galleries, dog demonstrations, and decoy carvers, and remains the main fundraiser for waterfowl-habitat conservation on the Eastern Shore. The Inn at Perry Cabin, technically just outside town in St. Michaels but easier to book from Easton, runs as the most recognised hotel on the Eastern Shore. For everyday meals, the Sunday brunch at Out of the Fire keeps a regular line.

Chincoteague, Virginia

Every July, the Chincoteague Volunteer Fire Company swims a herd of wild ponies across the Assateague Channel and auctions off the foals to fund the department's operations. The Pony Swim has run since 1925 and was made nationally famous by Marguerite Henry's 1947 novel Misty of Chincoteague, which remains the source of nearly every nine-year-old's interest in the town. Outside Pony Penning week, Chincoteague functions as the gateway to the Virginia end of Assateague Island National Seashore, with the Chincoteague National Wildlife Refuge covering about 14,000 acres of marsh, beach, and pine forest. The Assateague Lighthouse, a red-and-white-banded 1867 brick tower, climbs to a viewing platform looking over the refuge. AJ's on the Creek and Steamers Seafood Restaurant both lean heavily on local clams and the famous Chincoteague salt oysters.

Cambridge, Maryland

The Harriet Tubman Underground Railroad Visitor Center, opened on March 11, 2017 on Route 335 just outside Cambridge, sits in the heart of the Eastern Shore landscape Tubman knew as a girl and where she returned repeatedly to lead enslaved people north. The visitor centre anchors the 125-mile Harriet Tubman Underground Railroad Byway, which connects more than 30 sites across Dorchester and Caroline Counties. The Choptank River Lighthouse, a 2012 replica of the original 1871 screw-pile, sits at Long Wharf Park in downtown Cambridge with a small museum inside. Sailwinds Park hosts the summer concert series. Blackwater National Wildlife Refuge, 12 miles south, supports one of the largest breeding populations of bald eagles on the East Coast outside Florida. The 25-mile Tubman Byway segment through the refuge is one of the best self-guided drives on the Delmarva Peninsula.

The Bay's Best Long Weekends

The Chesapeake's small towns reward visitors who pick one and stay put rather than try to hit all ten in a single trip. Annapolis carries the heaviest history and the most to see in a single weekend. Cape Charles and Solomons Island both offer swimmable beaches without the Ocean City crowds. Onancock and Chincoteague give the clearest sense of the bay's working watermen culture, and the Tangier ferry out of Onancock is the main public way to reach the most isolated settlement in the Chesapeake. Easton and St. Michaels pair well as a single trip across the central Eastern Shore. Cambridge and the Harriet Tubman sites stand on their own as a focused historical visit.