These 6 Towns On The Chesapeake Bay Have Bustling Main Streets
The world’s third-largest estuary and the largest in the United States, Chesapeake Bay is one of a kind. This beautiful area is where the Atlantic Ocean rushes inland, cutting through Maryland to the north and Virginia to the south. First settled in the 1600s, the region around the bay is now a thriving tourist destination, drawing millions of visitors every year to enjoy the water and explore its quaint small towns. Here, on the busy but beautiful streets of Chesapeake Bay’s small communities, you’ll find so much to discover that it won’t be long before you’re planning a return visit.
Chesapeake City, Maryland
Historic Chesapeake City was a thriving hub as early as the 17th century, thanks to its proximity to the Delaware River. Today, the town’s south bank is listed on the National Register of Historic Places. Crowded with gems of 19th-century architecture, this area is a great starting point for getting to know the town. Visit the Chesapeake City Museum, housed in Franklin Hall, which was built in 1870, to discover the town's history over the centuries.
The museum is just next door to the beautiful Pell Gardens, a natural oasis on the waterfront where visitors can catch a concert, enjoy a picnic, or simply sit and watch the activity at the busy docks. This is the place to be if you want to explore the water for yourself - Chesapeake Water Tours offers a variety of excursions, from sunset cruises and craft beer tastings to fall foliage trips and daily sightseeing tours. Back in town, stroll along the waterfront to Canal Creamery to pick up a delicious cone or sweet treat while you enjoy the view.
Chestertown, Maryland
Now a busy college town on the Chester River in east Maryland, Chestertown began in 1706 as a small fishing village. This pretty community is known for its 18th-century architecture, picturesque streets, and lively atmosphere. In summer, the town comes alive with bustling farmers markets and open-air concerts but one of the biggest highlights in its seasonal calendar is in December when Victorian London takes over Main Street. A Dickens of a Christmas is an annual festival taking visitors back in time to holidays of the 1800s and features carriage rides, costume parties, and more in the heart of Chestertown’s historic district.
But you don’t have to wait until December to enjoy Chestertown. Beautiful at any time of year, downtown has lots to see and do. Pick up a self-guided walking tour map at the Visitors Center to stroll by sights, including the 1767 Georgian-style mansion the Wickes House, the Buckes House, built 1735-50, and Widehall, built in 1770 by Thomas Smythe, head of Maryland’s Revolutionary Provisional Government from 1774.
If you’re in the mood for shopping, browse the quirky selection at Bee Crafty Antiques. It’s easy to lose a few hours in this fascinating emporium of vintage items, antique furniture, collectibles, and gifts. Nearby is Bad Alfred’s Distilling Co, a great spot to take a break and enjoy local craft brews along with a classic Maryland crab cake.
Havre de Grace, Maryland
Havre de Grace is a charming small town at the top of the bay, where it meets the Susquehanna River. Enjoy stunning views along the Havre de Grace Promenade, a 0.75 mile scenic boardwalk that starts in town and follows the river to the Concord Point Lighthouse. Built in 1827, the lighthouse is the second oldest in Maryland and open to the public on weekends from April to October.
Head back along the Promenade to visit the Havre de Grace Maritime Museum and learn about the town’s origins from the Native American communities that settled the area 400 years ago, through the War of 1812, and up to the present day. You can even help make a traditional sailing skiff in one of the interactive exhibits! Another nearby must-see is the Havre de Grace Decoy Museum. This unusual museum celebrates the art of decoy making and is home to one of the largest collections of working and decorative Chesapeake Bay waterfowl decoys in the country.
Yorktown, Virginia
Yorktown is a small community with a lot of history. This key port town was the site of the final battle of the American Revolution in 1781. There are two buildings on Main Street that date back to the Revolutionary War period: the 1726 Cole Digges House and the 1696 Somerwell House. Both are well worth a visit today; the Cole Digges House is now Mobjack Coffee Roasters, where you can grab a latte and a snack; next door, the Somerwell House is home to Little York Confectionery, which offers homemade chocolates and candies.
Little York Confectionery is also where you can board the Steamer Wagon National Park Battlefield Riding Tour. This hour-long ride on a replica Stanley Steamer Wagon takes visitors through Yorktown and out to Colonial National Historical Park, where America’s independence was won.
The tour ends where it began, back in town at the Little York Confectionery. It’s a short walk from there to other Yorktown landmarks such as the Yorktown Custom House, one of only 12 historic Custom Houses in the United States, and Nelson House, home of Thomas Nelson Jr, one of the signers of the Declaration of Independence. If you’ve had enough history, head a block north to see the waterfront, where you’ll find Yorktown Beach and can get out on the bay with a scenic schooner tour from Yorktown Sailing Charters.
Cape Charles, Virginia
On Virginia’s eastern shore lies the vibrant community of Cape Charles, founded in 1886. A beachy destination, this laidback town is all about the outdoors. You can access the beach from every block along the main thoroughfare of Bay Avenue. Here, you can rent a kayak, go boating, swim, or just soak up the sun.
At the southern end of the beach is a large fishing pier for keen anglers to test their skills. At this end of the beach, Bay Avenue turns inland around the harbor and becomes Mason Avenue, where you’ll find dozens of inviting shops, cafes, and restaurants. Browse the tempting selection at Brown Dog Ice Cream or have something more substantial at Mason Avenue Bakery, a classic small-town bakery with homemade pastries, pies, cakes, and sandwiches.
Irvington, Virginia
On the banks of Carter Creek, off the Rappahannock River, Irvington is a scenic town with plenty of character and creekside charm. Next to the town Commons, you’ll find the Steamboat Era Museum, which highlights the importance of this centuries-old mode of transport to the town and details the historic era of the steamboats of the Virginia tidewater.
A short walk up the street from the museum is another unmissable Irvington attraction, the Dog and Oyster Micro-Vineyard. In operation for over a decade, this beautiful restaurant and inn is an unforgettable dining experience where you can pair local wines with ‘just out of the water’ oysters.
From May to October, on select weekends, you can browse the Irvington Farmers Market, known as one of the best in Virginia for its wide selection of produce, flowers, plants, farm-to-table foods, and crafts. Don’t worry if you miss it, there are lots of fun stores to explore in town where you can pick up a one-of-a-kind souvenir. Visit Objects Art and More to browse pottery, paintings, sculptures, and jewelry from local artists, or drop by Daily Magic to pick up holistic and natural gifts, including healing tea blends, bath soaks, herbs, and skin care.
Bustling Bayside Communities
Strolling quaint 19th-century streets to breathe in the salt-laced bay breezes — these Chesapeake Bay towns are the perfect place to relax, unwind, and get away from it all. Try your hand at building a traditional skiff, snack on Maryland crab, see where the Revolutionary War fought its final battle, take a sightseeing cruise in a classic schooner, or simply wander the waterfront. Whatever you’re up to, Chesapeake Bay has something for everyone in its eclectic and vibrant towns. These are small communities with big hearts and an even bigger welcome.
