10 Underrated Small Towns to Explore on the Chesapeake Bay
When Captain John Smith first laid his eyes on the lands of Chesapeake Bay, he could not help but be amazed by its natural beauty. Beautiful rolling hills, majestic rivers flowing to the bay, and shores teeming with oysters and other marine life are just some of the Chesapeake Bay delights the captain saw, which we can still experience today.
Tourists usually flock to popular Chesapeake Bay cities, like Annapolis and Baltimore, to experience the best of the area. However, the smaller and often overshadowed towns are just as impressive as their famous neighboring cities—with more small-town appeal to show for it. It’s time to put these destinations in the spotlight! Here are 10 underrated small towns to explore in the Chesapeake Bay.
Easton, Maryland
Evoking an elegant charm from its colonial-era architecture, Easton evolved from being a courthouse settlement during the 18th century into a beloved art hub on the eastern shores of Chesapeake Bay. The Academy Art Museum is the biggest art institution in town, with Avalon Theatre, The Trippe Gallery, and Troika Gallery as other stops for art enthusiasts.
Join Easton residents every first Friday from April to December for its Art Walk, where you can meet local artists and see their works. Eager to try your hand at outdoor painting? How about a quick drawing competition (of the pencil and paintbrush kind)? If your answer to both is yes, pack your art bag and head to Easton’s Plein Air festival every July. Complete your vacation at Easton by staying at the historic Tidewater Inn and trying Hunter’s Tavern’s elevated American fare.
Yorktown, Virginia
Despite only having around 200 residents, as listed in 2022, Yorktown is teeming with activities in the Chesapeake Bay thanks to its rich colonial history. Any Yorktown vacation should start with the Colonial National Historical Park, where you’ll learn about the lives of Captain John Smith and Pocahontas, as well as George Washington’s battle with the British Army. Follow it up with the American Revolution Museum to discover how the United States started as a country.
If you want to explore Yorktown in style, you can sail around Yorktown and watch the sunset from the York River via the Schooner Alliance II or ride an antique steamer wagon! Yorktown Cottages and Yorktown Beach Hotel are excellent accommodation choices, with the former closer to historical spots and the latter having riverfront views. Don’t forget to bring back some sweet treats from Little York Confectionary!
Oxford, Maryland
With its 300-year-old inn and ferry, Oxford knows how to celebrate its heritage and the bountiful waters of Chesapeake Bay. To experience the town’s well-kept history, visit the Oxford Museum and stay a night or two at America’s oldest full-service inn, the Robert Morris Inn. Then, enjoy a cruise down the Tred Avon River via the oldest privately owned passenger boat, the Oxford-Bellevue Ferry.
Stroll through Oxford’s tree-lined streets with white picket fences as you tour some of its oldest buildings. The Byberry & Calico House is the town’s oldest house, dating back to 1695, while the Grapevine House, built in 1798, had its unique grapevine imported from the Isle of Jersey. For boat enthusiasts, the Tred Avon Yacht Club has appealing info on boat races, as well as sailing programs for kids and adults. Lastly, spice up your book collection with Mystery Loves Company, an Oxford bookstore that specializes in the mystery genre.
Solomons, Maryland
From its marine laboratory and museums to its charter boats and oyster feasts, this quaint boating town has a lot of activities perfect for families looking for a Chesapeake Bay vacation. Adults and children alike will enjoy the Calvert Marine Museum and its exploration of the bay’s prehistoric past, wildlife, and history. The Chesapeake Biological Laboratory’s visitor center offers a more science-y outlook on the bay’s natural environment.
For a hands-on look at the waters surrounding Solomons, rent a boat through Solomons Boat Rental or Bunky’s Charter Boats. With this, the town has an arts center, the Annmarie Sculpture Garden, with a “pay what you can” system for its entrance fee. Need an inn for the night? Solomons Victorian Inn is one of the top bed-and-breakfast options in the area. It’s also near The Lighthouse Restaurant and Tiki Bar and Grill Solomons, known for their fried oysters and mai tai, respectively.
Onancock, Virginia
Many tourists consider Onancock a hidden gem in the Chesapeake Bay (Captain John Smith calling it “the gem of the eastern shore,” would agree) thanks to its historic theaters, preserved mansions, and diverse culinary scene. Catch a musical at the North Street Playhouse—East Virginia’s only year-round live theater, or watch a movie at the old-timey cinema of Roseland Theater. The latter even has monthly film festivals from May to August.
Onancock’s history is equally vibrant. Ker Place, an 18th-century Georgian-style mansion built by a local merchant, is open to visitors who want a glimpse of the life of the wealthy. Watermen’s Museum focuses on Onancock’s maritime heritage, while Samuel D. Outlaw Blacksmith Shop Memorial Museum and Hopkins & Bro. Store are the town’s old smithy and mercantile traders. Onacock is also proud to have The Blarney Stone Pub, Eastern Shore’s original Irish pub, and The Spinning Wheel, the town’s first bed and breakfast.
Rock Hall, Maryland
A proud member of the National Chesapeake Scenic Byway for its natural, cultural, scenic, and recreational attractions, Rock Hall is one of the best small towns to explore in Chesapeake Bay. Start with the Rock Hall Museum to see amazing model ships, fishing exhibits, and artifacts from Rock Hall’s past. Meanwhile, the Watermen’s Museum will educate you on the outdated ways of fishing, crabbing, and oystering.
Rock Hall’s marina is always open for any visiting boats, but the Shardana Sailing Charters Inc. also offers half-day or full-day sails for tourists without a vessel. Rent a room at Black Duck Inn for waterfront views and its proximity to the crab paradise Waterman’s Crab House, so you can comfortably eat to your fill in peace.
Saint Michaels, Maryland
Among the cluster of harbor towns in Maryland’s Eastern Bay, Saint Michaels stands out for its notable history and high-quality establishments, amenities, and activities. Saint Michaels Harbour Inn, Marina & Spa is the most luxurious accommodation in this cluster, offering commodore-themed quarters and fancy waterfront rooms. Add a sailboat tour via Sail Selina II to complete your Saint Michaels nautical vacation.
For history enthusiasts, the “town that fooled the British” has a variety of museums and stops that showcase its history. The Chesapeake Bay Maritime Museum is the biggest maritime museum in the area, and it has vessel exhibits, hands-on sailing experience, and educational cruises. The Hooper Strait Lighthouse, St. Michaels Museum, and the Classic Motor Museum for car lovers are other Saint Michael's points of interest to visit.
Mathews, Virginia
If you truly want a quaint and tranquil vacation in Chesapeake Bay, the sleepy town of Mathews may be your best bet. Upon arrival, make the Mathews County Visitor and Information Center your first stop so you can get maps, pamphlets, and even a driving tour around town. The visitor center is located in Sibley’s General Store, which also offers unique Mathews souvenirs.
Cross the street to go to the Mathews County Courthouse Square, where you’ll find the town’s historic 1795 courthouse, debtor’s jail, and clerk’s office. Down Brickbat Road, you’ll find the Historic Tompkins Cottage, which is the headquarters for the town’s historical society. Along Main Street, you'll also find Roane’s Antiques and the Bay School Community Arts Center. The highlight of Mathews, however, is the Mathews Maritime Museum, which is also just down Main Street. This fascinating museum has all the documents, photographs, and artifacts detailing the legacy of Mathews in America’s maritime heritage. Booking a stay at Hyco House Manor will fully immerse you in Mathews's history!
Tilghman Island, Maryland
With its waterfront location overlooking the Chesapeake Bay, Tilghman Island is the perfect destination for a romantic getaway in the Bay area. The Wylder Hotel, the most lavish and deluxe of all accommodations in town, offers a private marina to make your vacation even more intimate and personal.
You can rent a watercraft through Tilghman Island Marina & Rentals for a private sunset cruise, while sporty couples can plan a kayaking and paddle board combo excursion with Knapp’s Narrows. After a quick tour at the island’s tiny and only museum, spend the rest of your time admiring the island’s magnificent water views and fresh seafood. You can do fancy dining at Wylder Hotel Tickler’s Crab Shack or dine like the locals at the Tilghman Island Country Store.
Williamsburg, Virginia
In Williamsburg, you don’t just read about American history—you can actually live and immerse yourself in it! Colonial Williamsburg is an open-air “living history” museum with more than 300 acres of well-preserved 18th-century buildings. The first capitol building in Virginia, the Governor’s Palace, and one of the oldest continuously operating churches in the United States can be found here.
A room at the Williamsburg Inn will give you an extravagant stay near the famous museum. You can also rent one of the Colonial Houses in the district to experience a bygone era of America’s past. Need some non-history activities to do? Visit the vineyard of Williamsburg Winery, tour the 2-acre landscape of Williamsburg Botanical Garden, and chow down with the locals and fellow tourists at Brickhouse Tavern.
With the amazing beauty and rich history of the Chesapeake Bay region, it would take an entire lifetime to fully explore the area and discover everything it has to offer. Thankfully, you don’t have to waste too much time in crowded Maryland and Virginia cities to experience the wide range and blend of delights of the region. Why gather at the usual tourist spots when there are underrated and hidden gems waiting for you at the bay?
From harbor museums and historical charter boats to private beachfront hotels, colonial houses, and delicious oyster feasts, these are some of the best small towns to explore in Chesapeake Bay. Whether you’re only planning a short trip or a full weekend getaway, these destinations will surely fulfill your Chesapeake Bay wanderlust!
