Aerial panoramic view of Oxford, Maryland.

7 Coolest Towns in Chesapeake Bay for a Summer Vacation in 2024

Anyone looking for that quintessential town with cool experiences that leave lasting memories? The Chesapeake Bay on the Atlantic Coast is the largest estuary in the US and the world's third largest. Touching six states, like the eastern seaboard of Maryland and Virginia, as well as Washington, DC, the Chesapeake Bay region is home to over 18 million people and 3,600 plant and animal species.

With a cool blend of small towns around the bay area, there is something for every traveler's taste, like history along the colonial waterfront of Victoriana in Cape Charles or the outdoor paradise in Onancock. Discovering what makes each town special feels like digging through scrumptious layers of Smith Island Cake, from oysters and wine in Irving to the art spaces in St. Michaels.

Cape Charles, Virginia

Aerial view of the Central Park in Historic Cape Charles, Virginia.
Aerial view of the Central Park in Historic Cape Charles, Virginia.

Located in Northampton County on Virginia's Eastern Shore, this town on a small peninsula is one of the southernmost in the whole bay region. Truly a hidden gem in between the Chesapeake Bay to the west, King's Creek to the north, and Old Plantation Creek to the southeast, it's easy to fall in love with the prevalence of southern hospitality and sunny skies. Cape Charles' waterfront is lined with Victorian-era buildings, while the 17.6-mile complex of the Chesapeake Bay Bridge Tunnel spans across the mouth of Chesapeake Bay, the Eastern Shore National Wildlife Refuge, and Kiptopeke State Park. The town's own Central Park, at the heart of the historic downtown, flaunts a large pergola, gazebo, benches, and a beautiful fountain.

Established in 1886, Cape Charles, home to around 1,000 and 2,817 acres of land, is never overcrowded despite being the largest and most dynamic town around. Home to one of the US's last remaining rail barges across the Chesapeake Bay to Norfolk, the historic Bay Haven Inn is a beautiful piece of architecture from 1906, and the Cape Charles Memorial Library at the corner of Mason Avenue and Pine Street is worth a quaint visit. From the cozy Coastal Baking Co. to sandy beaches, the gentle waves beckon for water sports like paddleboarding, kayaking, kiteboarding, and jet skiing. With a diverse culture, golf, harbor, marinas, boat ramps, sport fishing, summer rentals, and B&B, Cape Charles Town Beach along Bay Avenue offers free public access at the end of every block, with free parking and the adjacent Cape Charles Fishing Pier and LOVEwork.

Irvington, Virginia

Irvington, Virginia. In Wikipedia.,_Virginia By Nyttend - Own work, Public Domain,
Irvington, Virginia. In Wikipedia. By Nyttend - Own work, Public Domain, Wikipedia

Nestled along the Rappahannock River and its oyster beds, Irvington really fancies oystering nearly as much as sharing this passion in every way and form. Visitors can take a harvesting tour to see and learn how this species is vital not only to the industry but also to the health of the aquatic environment. Oysters go well with wine and top-notch sights, and there's no better place to experience all three than at the Dog and Oyster Vineyard restaurant’s signature oyster bar. From sailboat races to birdwatching and all types of seafood dining, Irvington also attracts birds like osprey, herons, and nesting eagles for a share of delicacies from the water.

Many of the historic houses are on the National Register of Historic Places, while the farmer’s market on the first Saturday of every month has a great local feel to browse for gifts like flowers, produce, baked goods, and folk art. Visitors can discover another significant historical connection to the ocean at the Steamboat Era Museum with its antique and authentic items, important documents, hands-on activities, and displays from when the steamboats ruled the Chesapeake Bay. Just north, the historic 1735 Christ Church & Museum is a window into colonial times with its brick door frames, tall benches, and stone floors, as well as property grounds for a stroll under timeless charm.

Onanock, Virginia

Onancock, Virginia. In Wikipedia.,_Virginia By JodyMBrumage - Own work, CC BY-SA 4.0,
Onancock, Virginia. In Wikipedia. By JodyMBrumage - Own work, CC BY-SA 4.0, Wikipedia

For the love of the outdoors, go to Onancock, the scenic heart of the Eastern Shore between the bay and the sea. This small town next to the Tangier Sound is a dream for nature lovers, with clear waters and bountiful sea creatures. No wonder the seafaring Captain John Smith was dazzled by the area four centuries ago that spurred a small town, now home to some 1,200. An idyllic blend of old and new, Onancock flaunts museums, concert venues, and cuisine, peppering the vibrant downtown with galleries at each turn. No doubt the natural world attracted artists, inspiring it to turn its historic high school into an individual, welcoming studio to see the creative process.

Visitors can find their own flow, another call, or simple inspiration at the live theatre with Main Stage productions, presenting professional, local, and even high school actors, or in the traditions and southern hospitality at its finest. From maritime-themed pubs to five-star dining, premium bed and breakfasts, and boutique hotels, don't miss the cool Roseland Theatre, a cinema from the 1950s with old-time charm and new releases. When you visit in time for the local farmers' and artisans' outdoor market in town with live music, take a Tangier Island ferry in the breeze to the bay's hidden treasures, May through October. Alternatively, Onancock Creek is great for paddling until the best sunset from the shore.

Oxford, Maryland

A beautiful view of Oxford, Maryland.
A beautiful view of Oxford, Maryland.

Oxford, one of the state's oldest towns, is also one of its coolest. Established in 1683 on the water's edge in the Chesapeake Bay, the stunning colonial facade is the Victorian-lined waterfront where some of the freshest seafood on the Atlantic Coast is caught, and people stroll along the relaxed parapet. From the Oxford Inn, a quaint 19th-century home, to a buzzing art scene at its heart, the best way to explore the heritage of Oxford is on a historic walking tour. After art at Oxford Community Center and a gift from Oxford Vintage & Trade, Doc's Sunset Grille, which is a crab house, sounds pretty fantastic for dinnertime.

Safe Harbor Oxford, with its poolside views of the Tred Avon River, blends warm, personalized touches of small-town charm with upscale marina amenities just a hop from the Water's Edge Museum. Home to other historic houses, churches, and important sites, the Oxford Museum, right in the town's center, whispers local stories and shares cultural treasures from the region's seafaring past. After peeking back in time, the Oxford-Bellevue Ferry is a breezy journey on one of the nation's oldest ferries to peacefully cross the river—an Instagrammable moment. Campbell's Boatyards - Jack's Point is a scenic, full-fledged boatyard, while Campbell's Boatyards - Bachelors Point is a great place to catch the sunset.

Smith Island, Maryland

Kayaking at Smith Island in Maryland.
Kayaking at Smith Island in Maryland.

Isolated in the middle of Chesapeake Bay, Smith Island is all-around intriguing. From its distinctive Elizabethan accents, carried over from one of the oldest English settlements in the region to the miles of untouched marshland waterways with creatures that watch kayakers, Goat Island hosts non-indigenous goats that have a mind of their own. If you prefer a pedal over a paddle, a bike can take you into the most scenic corners through spectacular views like Rhodes Point. No trip is complete without tasting the layered goodness of Smith Island Cake, with an icing of your choice or traditional chocolate, the state's official dessert, which was born here.

Smith Island Bakery, the best place to try it, is a hit in the morning before a stroll along Shanks Gut, a park. This obscure island, from the eye of a stranger, is home to a family-friendly atmosphere and hospitable 453 locals, with a unique culture and way of life to discover in various ways for each taste and age. Don't miss the Smith Island Cultural Centre Museum for all this and more through accessible and immersive documentaries, cultural artifacts, and other memorabilia. The Bayside Inn will bathe and tuck you in, so to speak, with a feeling of home on this strange island, but not before a delicious seafood feast, that is, if not staying at the elegant Island Time B&B.

Solomons, Maryland

Colorful Solomons Island Sunset reflected on the Patuxent River with a pier.
Colorful Solomons Island Sunset reflected on the Patuxent River with a pier.

Solomons juts out into the water at the southern tip of Calvert County. Inarguably, this peninsular town is one of the Chesapeake's coolest summer getaway ideas to really get away, between the Patuxent River to the west and the bay to the east. The boardwalk is a great place to start on a relaxed stroll against river views, with shopping and dining along its path on one side and passing boats on the other. Despite the remote vibes, Solomons is a very family-oriented town with attractions like the Calvert Marine Museum. Featuring exhibits and programs on the area's maritime legacy, there's also a paleontology section with ancient animal fossils.

Drum Point Lighthouse is a must-see old, fixed-up lighthouse with tours around its specific history along the sea and unbeatable views of Chesapeake Bay from up high. Nearby, the Pier Restaurant is, as expected, at the base of the pier, while just south of there, the Lighthouse Restaurant and Dockbar is the most popular place to eat in town. From the Calvert Marina Solomons and Solomons Creeks Sanctuary across the water to the east, no summer day is complete without a high swirl from the Cone Island Ice Cream Shoppe. Enjoy one on a boardwalk stroll at sunset, at a gazebo, or while the kids enjoy the playground, among other scenic spots to relax.

St. Michaels, Maryland

Chesapeake Bay with boats St Michaels, Maryland, USA.
Chesapeake Bay with boats St Michaels, Maryland, US.

St. Michael's has a calming ambiance that takes effect immediately and sees many returning times and again when the soul needs some serious soothing. Others know of the spectacular water sports opportunities in the bay, which reflect the sparkle in your eye and glitter just a little more around these parts, under sail, boat, kayak, or a lively fishing rod. The Chesapeake Bay Maritime Museum is a destination in itself for culture fans, families, maritime lovers, and historians with intriguing photographs, maps, and interactive exhibits for all ages, while the Crab Claw is a hit for waterfront dining.

From antique shops to art galleries throughout the town, the quaint Waterfront Park is great for a morning stroll or a bike ride to meet the sunset that lights up historic buildings in a soft rose glow. Don't miss the unique 1879 Hooper Strait Lighthouse, CBMM, built to guide vessels through the shallow, dangerous shoals of Hooper Strait. This screwpile lighthouse, with a sea hatch and lookout, was once located in the middle of the bay. The town's own Patriot Cruises is a popular tourist attraction for exploring the open ocean "in a breeze," while couples in particular love the Moonlight Cruise option with Sail Selina II under the white sails and the moon.

So, welcome to the largest estuary in the US, perfect for summertime watersports, boardwalk strolls, and island hopping. The quirky Smith Island would feel strange with its Goat Island of free-roaming non-indigenous goats if it weren't for the inventor of the layered Smith Island Cake, Maryland's official dessert. Onancock dazzled the seafaring Captain John Smith over four centuries ago, while in Oxford, visitors can take the Oxford-Bellevue Ferry for a breezy journey on one of the nation's oldest ferries to peacefully cross the Tred Avon River.

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