7 Chesapeake Bay Towns With Unforgettable Main Streets

The Chesapeake Bay’s 11,684 miles of shoreline provide the states of Maryland and Virginia with some of the prettiest scenery in America’s Mid-Atlantic region. The largest estuary in the United States, it long served as a nautical super highway, ferrying everything from grain and seafood to troops and weapons between Revolutionary-era ports and Civil War-era shipyards. Dubbed the “Mother of Waters,” the Bay’s inlets and coves continue to shelter many small communities worth visiting, the best of which feature picture-perfect main streets. Boasting attractive old Victorian-era storefronts, top-notch restaurants serving fresh seafood, as well as cozy inns housed in old mansions, each makes an idyllic setting for an unforgettable day trip, a weekend getaway, or even an extended family vacation. Here’s where to find Chesapeake Bay’s most memorable small-town main streets this year.

Onancock, Virginia

Established in 1680 on Virginia’s Eastern Shore, Onancock’s downtown is dissected by Market Street, long used as the town’s main thoroughfare. And it’s a somewhat curious route, doing a 180-degree loop back on itself at the south branch of Onancock Creek before eventually joining King Street (picture a paperclip and you’ll know what I mean). It’s worth walking both sections of Market Street, stopping at the town’s old wharf from where skipjacks, the oyster vessels of old, would deliver their catches to Baltimore across the Bay.

At the other end of Market Street, the opulent red-brick Ker Place is the focal point. Built in 1799 and the best example of a Federal mansion on America’s Atlantic Coast, it offers guided tours that provide an up-close look at its elegant original interiors. Round off your visit with a stay in the historic Charlotte Hotel, a quaint boutique hotel set in a 1907 bank just steps away from Market Street (and book a table at the on-site restaurant).

Havre de Grace, Maryland

Less than an hour northeast of Baltimore, Havre de Grace is an ideal spot for an authentic Chesapeake Bay experience. Washington Street is considered the main drag here and is an ideal place to begin exploring this pedestrian-friendly town. From here, it’s just a short stroll to the 36-foot-tall Concord Point Lighthouse, built in 1827 and still guiding boats into the mouth of the Susquehanna River. The nearby Maritime Museum and Decoy Museum are also must-visit attractions and can be accessed via a wooden boardwalk connecting with Havre De Grace Basin Marina, with incredible Bay views along the way.

Time your visit for the Susquehanna Wine & Seafood Festival in September, when some 20-plus crab-shack and oyster vendors set up beside the lighthouse, backed by live bands and cooking demos… all just a few blocks from the main street area. Just a block west of Washington Street, the Vandiver Inn is set in an elegant Italianate mansion dating from 1886; it’s just a 10-minute walk from the lighthouse and museums.

Chestertown, Maryland

Attractive Georgian-era brick buildings line Chestertown’s High Street, the town’s colonial thoroughfare. Laid out in 1706, it encompasses much of Chestertown’s historic downtown core. Begin your self-guided walking tour at the Custom House at the eastern end of High Street, where it meets the Chester River. Part of the delightful Chestertown Historic Waterfront, it was built in 1746 and features original wood-panelled rooms that once warehoused tobacco for export.

A great time to visit is the last full weekend of May. That’s when the tall-ship Sultana anchors at the foot of High Street for the Tea Party Festival, a fun event featuring a costumed tea-tossing re-enactment. Come back in December for carriage rides and roasted chestnuts during the town’s Dickens of a Christmas, a two-day Victorian-themed fair that sees High Street all dressed up with festive lights and decorations for the Holidays. For an authentic Chesapeake Bay accommodation experience, book a night or two at the 18th-century White Swan Tavern. This restored pre-Revolution coaching inn features romantic fireplace suites and afternoon teas with cherry scones.

Cape Charles, Virginia

Mason Avenue, Cape Charles’ main drag, runs parallel to the town’s harbor and ends at the beachfront and fishing pier. While not a large community, it makes up for its small size in its picturesque setting, so have your camera ready as you wander. Downtown highlights include Peach Street Books, quite possibly the country’s quaintest bookstore and home to a huge selection of used and rare books. Afterwards, grab a scoop or two from Brown Dog Ice Cream, a local institution since 2012 (and yes, there was a brown dog in the story). Cape Charles Coffee House is also worthy of a stop and is set in an old bank building dating from 1912 that also serves up delicious sweet treats and breakfasts.

Wondering when to visit Cape Charles’ unforgettable main street? There’s always something going on in summer thanks to the town’s free Harbour for the Arts concert series. Held at the Historic Palace Theatre in Cape Charles Central Park, these Friday evening concerts feature everything from pop to rock and jazz music. You can bed down for the night near the action at Hotel Cape Charles on Mason Avenue, popular for its balcony views and concierge access to Bay Creek’s Arnold Palmer and Jack Nicklaus-designed golf courses.

St. Michaels, Maryland

Maryland Route 33 becomes Talbot Street as it threads its way past the quaint shops and rum distilleries that signal you’ve arrived in St. Michaels. Follow the route to the fantastic Chesapeake Bay Maritime Museum, home of the Hooper Strait Lighthouse and the Bay’s best boat-building exhibits. August is a great time to visit this sprawling attraction as it hosts the annual Watermen’s Appreciation Day with boating skills contests, steamed crabs, and family-friendly events.

As for where to stay, check availability at the St. Michaels Harbour Inn, Marina & Spa. Just a five-minute harborfront stroll away, this 3-star waterside property features cozy rooms and a restaurant with a patio and views over the Bay.

Yorktown, Virginia

A personal favorite, Yorktown is set at the eastern end of the magnificent Colonial Parkway, a 23-mile-long scenic route connecting it to Williamsburg and Jamestown, the other two colonial-era sites in Virginia’s Historic Triangle. As you enter town, stop first at Yorktown Battlefield National Historical Park. It was here that General (and later President) George Washington defeated the English in 1781, with remnants of the battle lines still evident. From here, follow Main Street past the Yorktown Victory Monument (stop for the views), Nelson House (1725), and the old Custom House (1884) down to Water Street, the town’s tourist center overlooking the wide York River.

Here you’ll definitely want to walk the town’s lovely boardwalk, stopping for a sit-down or a swim at Yorktown Beach, followed by a wander to Riverwalk Landing with its shops and eateries. October 18th is a great time to visit the American Revolution Museum at Yorktown for its artillery salute during its Victory Celebration marking Cornwallis’s 1781 surrender (the encampment demos and fife-and-drum parades are also fun). The family-run Hornsby House Inn on Main Street is a great place to stay in Yorktown and overlooks the York River and the Victory Monument.

Solomons, Maryland

While a tiny community, Solomons (aka Solomons Island) is set on the Patuxent River where it meets Chesapeake Bay and is a popular Maryland tourist destination. Island Road serves as the town’s main street before easing onto Charles Street, with a wooden boardwalk being perfect for a leisurely stroll. Must-sees include the Calvert Marine Museum, where the unique Drum Point Lighthouse, built in cottage style in 1883, is preserved onshore (check out the museum’s fossilized shark teeth, too).

Although a mile outside of town, the Annmarie Sculpture Garden and Arts Center is worthy of a visit. Featuring an easy forest loop and artworks on loan from the Smithsonian, it’s a delightful way to spend an hour or two. For overnight stays, the cozy Solomons Victorian Inn on Charles Street occupies an attractive 1895 Queen Anne building. Its harbor-view balconies, all just steps away from the dining experiences at the Charles Street Brasserie, make it an ideal spot to stay.

The Final Word

Each of these seven scenic towns proves that a great main street is a crucial component to communities looking to attract tourists. And yes, Chesapeake Bay’s best small towns have an advantage thanks to the connection between these thoroughfares and the waterways they’ve grown up around. Whether you’re a vacationer or a day-tripper looking for a fun mix of oyster festivals, art galleries, and classy boutique inns, these Mid-Atlantic communities on Chesapeake Bay offer up unforgettable main street experiences.