7 Serene Chesapeake Bay Towns For A Weekend Retreat
The Chesapeake Bay is the United States’ largest estuary, with a surface area spanning 4,479 square miles shared by the states of Maryland and Virginia. With its vast array of bayside beaches, connected rivers, and tranquil islands, the Chesapeake Bay has plenty of inviting options for an ideal weekend retreat. And since the bay also has a wealth of historic treasures, a cherished local seafood culture, and several highly acclaimed boutique hotels and resorts, it’s also a place to enjoy a surprisingly elevated getaway in the Mid-Atlantic region.
Whether you’re looking for a delectable foodie adventure, an enlightening historical journey, or a simply relaxing beach trip, here are seven serene Chesapeake Bay towns for a great weekend retreat.
Havre de Grace, Maryland
Situated along the northern reaches of Chesapeake Bay, about 65 miles southwest of Philadelphia (Pennsylvania), Havre de Grace is perfect for exploring a different side of the bay. For a deep dive into local seafaring culture, head to the Havre de Grace Maritime Museum and Environmental Center and learn some of the bay’s many fascinating stories, from the earliest days of British colonization in the early 17th century to the growth of the Underground Railroad where Black Americans escaped slavery in the 19th century and the growth of commercial fishing in the 20th century. Just a short stroll from the museum, the beautiful Concord Point Lighthouse has stood tall since 1827 by the point where the Susquehanna River flows into the bay.
Though Havre de Grace has plenty of history, this town also has plenty going on today. Hit the Cultural Center at the Opera House to catch a variety of live performances, from classic musicals to lively gospel concerts and more. To spot some wonderful works by local artists, check out the Havre de Grace Art Collective’s Gallery 220 and Arts by the Bay Gallery downtown. For a picture-perfect day on the greens, book a tee time at the top-ranked Bulle Rock Golf Course. For the ideal boutique hotel that combines country-style charm with a convenient location in town, check into the stately Vandiver Inn.
Chestertown, Maryland
Located on Maryland's Eastern Shore, about 75 miles east of Baltimore, Chestertown is a beautifully historic town that’s great for settling down and enjoying a relaxing long weekend. It’s also home to Washington College, the first college founded (in 1782) after the United States declared independence, and the college continues to enrich the local community with resources like the Gibson Center of the Arts and the Kirwan Meditation Garden. If you want to discover more local history, book a sailing journey on the Schooner Sultana that recreates the experience of an 18th century British Royal Navy boat, and stop at Sumner Hall to learn about Black soldiers’ contributions during the Civil War and the evolution of Black American culture since.
When you can use a simpler retreat into nature, go to the Lawrence Wetlands Preserve (LWP) for an 8.5-acre oasis spanning upland forest, wetlands and meadows, and a freshwater pond. If you fancy a different kind of exploration, try Dixon’s Auction at Crumpton, which has a constant array of auctions featuring many vintage treasures and unique finds for sale. And when you crave the ultimate long weekend full of rest, relaxation, self-care, and discovery, book a stay at Brampton 1860 for luxuriously well-appointed rooms, suites, and cottages sitting on 35 acres of landscaped gardens and pristine Eastern Shore forest.
St. Michaels, Maryland
It’s hard to discuss inviting Chesapeake Bay towns for weekend retreats without mentioning St. Michaels, a uniquely charming village about 81 miles east of Washington, D.C. You can start to sense this town’s special heritage at the Chesapeake Bay Maritime Museum, which includes everything from a working shipyard that preserves historic vessels to a floating fleet of boats and ships and the on-site Hooper Strait Lighthouse. If you want a more contemporary view of the waterfront, try St. Michaels Marina for boat docks, a village full of chic boutiques, and perks like pool access, wifi internet, and complimentary bikes to use for marina customers.
If you fancy some more vintage vibes, go to the Classic Motor Museum to find vintage farm tractors, antique motorcycles, and rare historic cars. When you seek some fine varietals, head over to St. Michaels Winery to savor some great Maryland wines, including chardonnays, pinot gris, and sparkling vidal blancs. (If you prefer beer, Eastern Shore Brewing is right next door.) To complete your perfect weekend in St. Michaels, check into exquisite five-star luxury at the Inn at Perry Cabin, which has a full-service spa, its own acclaimed golf club, and even its own fleet of catamarans and yachts for guests to book.
Smith Island, Maryland
Since this is Maryland’s one island that’s only accessible by boat (with ferries running from the Eastern Shore town of Crisfield), Smith Island feels remote and removed from the worries of the outside world. Come for the sweet treats of the beloved Smith Island Bakery, including the most authentic renditions of Maryland’s official dessert: Smith Island Cake. Stay a little longer to savor the classic Maryland seafood served at Bayside Inn Restaurant, including steamed crabs and real Maryland crab cakes.
For some more authentic local flavors, do a little field trip down to Drum Point Market on the south end of the island for special local souvenirs and tasty treats like crab cakes and hush puppies. Once you’re ready for some rest and relaxation, kick back and soak up the island vibes at the cozy Smith Island Inn.
Reedville, Virginia
Heading down to the lower Chesapeake Bay, we reach the lovely town of Reedville, about 119 miles southeast of Washington D.C. As a longtime Virginia fishing town that’s become one of the most important ports for commercial fishing, you can expect plenty of fascinating stories, cool exhibits, and a world-class collection of traditional sailing vessels at the Reedville Fishermen’s Museum. You can also get a taste of Reedville’s current maritime culture at the marina that has docks available for boats to park, as well as The Crazy Crab for anyone hungry to try some authentic local seafood.
If you crave some more local cuisine, go to Reedville Market and try all sorts of creative dishes featuring clams, mussels, haddock, salmon, and plenty more fish. (They also have some non-fish options.) For your own private beach retreat, book the Chesapeake Bay Beach House to enjoy a stay at an expansive five-bedroom house with a private beach and kayaks and bikes available for guests to use.
Irvington, Virginia
Only about 71 miles east of the hustle and bustle of Richmond, Irvington is a lovely coastal town that’s proud of its slower pace of life. You will get a good sense of what this town is all about when you sample the riches of The Dog and Oyster, a unique micro-vineyard and winery that specializes in crafting original Virginia wines and pairing them with locally harvested oysters. To sample some more local goodies, mosey over to Kellum Farms for the freshest seafood and produce alongside locally crafted desserts and hand-crafted souvenirs.
When you can use an easy day on the links, it’s hard to beat the gorgeous greens at the Golden Eagle Golf Club. And when it’s time to enjoy some more of the finer things in life, The Tides Inn has you covered with elegant waterfront rooms and suites, a full-service spa, ample sporting and fitness amenities on site, delicious in-house restaurants, and even its own creative arts programs.
Yorktown, Virginia
Yorktown has stood near the point where the York River flows into the Chesapeake Bay for well over three centuries, and this historic village (about 50 miles northwest of Virginia Beach) continues to amaze with its deep heritage. Yorktown is best known for the 1781 Battle of Yorktown, which resulted in British surrender and essentially guaranteed American victory in the Revolutionary War. You can relive this revolutionary history at the American Museum in Yorktown and its fully immersive exhibits. In addition, you can actually visit the Yorktown Battlefield, where this final battle of the Revolutionary War occurred, as well as the Watermen’s Museum by the river that shares the stories of the region’s maritime traditions.
While Yorktown has plenty of interesting historical sites worth exploring, it’s also a great place to create your own interesting stories. At Back Creek Park, take advantage of amenities like a free boat launch facility, a picnic area, a crabbing pier, and lit pickleball courts. Back in town, Yorktown Beach has two acres of golden sand, picnic grounds, and pleasantly calm water for swimming. After a long day wandering around town, settle down for a great night at the Hornsby House Inn, which has been welcoming guests to Yorktown for three generations.
Need an Easy Weekend Getaway? Stay and Play at the Bay.
With its rich assortment of historic treasures, natural wonders, and calming beauty, the Chesapeake Bay makes for perfect weekend retreats. At Yorktown, you can hit the beach after touring one of the most critical battlegrounds of the Revolutionary War. At Irvington and Reedville, taste the delectable heritage of the bay farm and hook-to-table food culture. At St. Michaels, indulge in the finer things in life, like well-crafted wines, classic cars, and luxury resorts. However you want to do your weekend retreat, the Chesapeake Bay has you covered with plenty of inviting options.
