8 Of The Most Captivating Small Towns In Chesapeake Bay
As the United States’ largest estuary, Chesapeake Bay makes a very inviting coastal playground that spans across the states of Maryland and Virginia. Along the bay, you will find plenty of captivating American history and established maritime traditions, but keep your eyes out for a few special surprises. Expect working fishing towns with the best catches of the day, but also prepare to spend a cool evening enjoying local craft wines and beers. Wander the streets to discover a wealth of captivating and creative art, and hit the beaches for all sorts of fun on the open water.
To get a better sense of what’s available in the region, here are our picks for eight of the most captivating small towns by the Chesapeake Bay.
Havre de Grace, Maryland
Located right where the Susquehanna River meets the Chesapeake Bay, about 65 miles southwest of Philadelphia (Pennsylvania), Havre de Grace is a quirky town where there’s always more than meets the eye. Head to Concord Point Lighthouse to see the very point where the river flows into the bay, and stick around to explore this 1827 lighthouse, where the first keeper was John O’Neill, a military officer who successfully defended the town from British forces during the War of 1812. Right next to the lighthouse, you will find the Havre de Grace Decoy Museum, a uniquely alluring place that lets you learn about Havre de Grace’s cherished tradition of crafting convincing decoys for hunting.
For a deeper dive into local history, make sure to visit The Havre de Grace Colored School Museum and Cultural Center and see how this one-time stop on the Underground Railroad has grown into a vibrant hub of Black culture. For a change of pace, head to Bulle Rock Golf Course for 18 championship-grade holes that regularly rank as Maryland’s best. From there, make your way to the Vandiver Inn for a centrally-located boutique hotel that somehow also looks and feels like the ultimate country inn retreat.
Stevensville, Maryland
Situated on the north end of Kent Island, about 45 miles south of Baltimore, Stevensville offers a pleasantly mid-Atlantic take on island time. Go to Terrapin Nature Park and experience this award-winning 276-acre preserve that stretches across wildflower meadows, coastal wetlands, thick woodlands, and sandy beach. For a different kind of beach day, try Matapeake Clubhouse and enjoy a lovely swimming beach, a designated dog beach, and a family-friendly picnic area.
Beyond the beaches, there’s plenty more to explore around Stevensville. Believe it or not, this is actually the home base for Paul Reed Smith Guitars, and you can book a factory tour to see the making of the guitars that musicians like Carlos Santana and John Mayer trust to make great music. It’s also worth stopping for a tasting at Mark Cascia Vineyards, a family-run operation that proudly hand-crafts premium wines. To complete your Kent Island experience, book a stay at Blue Heron Landing and relax at this cozy bayfront bed-and-breakfast.
St. Michaels, Maryland
The town of St. Michaels may only sit around 80 miles east of Washington, D.C., yet this charming maritime village makes for quite the picture-perfect getaway. Immerse yourself in local history and seafaring culture at the Chesapeake Bay Maritime Museum, a treasure trove of fun features like their working shipyard, the historic Hooper Strait Lighthouse, and their floating fleet of historic vessels that continue to sail the bay. For another perspective, head over to Waterfront Park and hike or bike the St. Michaels Nature Trail to enjoy the serene vibes and lovely views.
If you can use some refreshments after wandering around town, feast on some tasty house-made pizzas and pastas at Ava’s. For some more adult beverages, stop at St. Michaels Winery and sample some delectable Maryland wines. And for the ultimate in local hospitality and world-class luxury, treat yourself to a sumptuous stay at the Inn at Perry Cabin. Not only will you get a beautifully appointed room or suite, but you will also have access to the Inn’s soothing full-service spa, the 18-hole Links at Perry Cabin golf course, and even their private fleet of boats reserved just for guests.
Cambridge, Maryland
About 90 miles southeast of Washington, D.C., you can discover one of the East Coast’s oldest colonial-era settlements at Cambridge, one that’s since matured into a delightfully scenic community. For a fascinating throwback, head out to the Dorchester County Historical Society’s campus to tour a beautifully restored 18th-century house and peruse their extensive collection of local historic artifacts. The Harriet Tubman Museum and Educational Center is where you can learn more about the life and times of this legendary leader of the anti-slavery movement, as well as the larger history of Black communities on the Eastern Shore. The physical building is closed temporarily for renovations but still offers walking tours. For a deeper dive into Underground Railroad history, Harriet Tubman Underground Railroad National Historical Park is worth the quick drive.
Back in Cambridge, it’s fun and easy to poke around historic downtown by the Choptank River, and it’s even better when you make it to the Choptank River Lighthouse to tour this well-constructed replica of the original 19th-century lighthouse that helped boats navigate this end of Chesapeake Bay. Then, head over to the Hyatt Regency Chesapeake Bay and enjoy this grand resort complete with the 18-hole River Marsh Golf Club, a marina with 150 boat slips, full-service Sago Spa, and a great variety of family-friendly rooms and suites.
Irvington, Virginia
Only about 70 miles east of Richmond, escape to a quaint and tranquil bayside village, one that abounds in natural beauty and tasty surprises. If you’re sailing into Irvington, park your boat at Carters Cove Marina for deep water slips, excellent storm protection, and the ideal launchpad for scenic excursions on the protected waters of Carters Creek. Meanwhile, in town, check out the Steamboat Era Museum to experience more of the region's rich maritime heritage. Just a short stroll from the museum, the Hope & Glory Inn is where you will find The Dog and Oyster, a micro-vineyard that crafts incredible Virginia wines and pairs them with the freshest locally-caught oysters.
If you’re down to explore more of the local wine scene, do a little field trip with a designated driver to Good Luck Cellars to see for yourself their gorgeous Northern Neck vineyards and try their delectable takes on varietals like Chardonel, Viognier, Cabernet Franc, and Norton. Otherwise, check into the legendary Tides Inn for an expansive waterfront resort that offers a wide array of sailing excursions on the bay, along with world-class farm-to-table dining and lovely maritime-themed accommodations.
Yorktown, Virginia
Situated on the banks of the York River, Yorktown offers a fully immersive historic getaway that’s only about 35 miles north of Norfolk. Of course, no trip here feels complete without a visit to the Yorktown Battlefield to see the spot where General George Washington led American and French forces to besiege the British army and essentially secure American victory in the Revolutionary War. For even more Revolutionary War stories, pop over to the American Revolution Museum at Yorktown to explore a vibrant re-creation of an 18th-century tobacco farm, tour a re-created Continental Army encampment, and view their fascinating exhibits. And at the Watermen’s Museum, you can dive into the community’s relationship with Chesapeake Bay from the colonial era to present day.
If you’d like to head out on the water and experience it for yourself, you’re in luck, as Yorktown Beach offers two acres of fully-accessible sandy shores perfect for swimming, boating, and fishing. And just a few blocks inland, you can stay at the Hornsby House Inn for easy access to the waterfront and museums, as well as classic Hampton Roads hospitality.
Cape Charles, Virginia
Once you take the Chesapeake Bay Bridge-Tunnel from Virginia Beach, you will reach the cool coastal community of Cape Charles. If you want a relaxing day at the beach, head to Kiptopeke State Park for exceptional birdwatching and a pleasant bay beach for swimming. Or, if you crave a more exciting excursion, take the ferry or sail over to Smith Island to explore its pristine beaches on the Atlantic Ocean, spot local wildlife, and catch a glimpse of the towering Cape Charles Lighthouse that was built here in 1895.
When it’s time to get some refreshment after a big day at the beach, hit up Cape Charles Brewing Company for local craft beers and casual pub fare, or try Hook @ Harvey for an elegant waterfront bistro serving up satisfying surf-and-turf and legendary sunset vistas. Then, make your way to the Bay Haven Inn, a cozy bed-and-breakfast right in the heart of town.
Chincoteague, Virginia
Only around 60 miles south of Ocean City (Maryland), Chincoteague may be Virginia’s most famous island, thanks to the resident wild ponies who inspired the 1947 classic children’s story by Marguerite Henry, Misty of Chincoteague, as well as the 1961 film Misty that’s based on the book. Be sure to visit to the Chincoteague Pony Centre to see some up close. They even offer pony rides for small children! In addition, you can learn more of Misty’s backstory at the Museum of Chincoteague Island, and it’s worth a longer stop to see artifacts from past shipwrecks, a decoy carver’s workshop, and other cool nooks and crannies.
From the main village of Chincoteague, it’s a short drive or walk across the bridge to Assateague Island, which has the famed red-and-white striped Assateague Light that’s been illuminating this stretch of the Eastern Shore since 1867. While here, it’s also worth visiting the gloriously unspoiled ocean-facing beaches of Chincoteague National Wildlife Refuge. Once you’re ready to call it a night, Refuge Inn, a family-run boutique hotel, will make you feel right at home.
For Captivating Charm and Unmatched Beauty, Sail Away to Chesapeake Bay
While the United States’ Atlantic coast has a number of wonderful attractions and features worth visiting, don’t skip the incredible offerings of the Chesapeake Bay region. Go to Stevensville for the unique beauty and soothing vibes of Kent Island, and head to St. Michaels for an elegant resort town with a proud maritime pedigree. Try Yorktown for a wealth of fascinating historic treasures, and visit Chincoteague to experience the coastal environment that inspired the classic Misty stories. With so much to see and do across the Bay, there’s never a bad time to sail away.
