View of the Chesapeake Bay shore along Cape Charles, Virginia.

The Best Small Towns in the Chesapeake Bay for a Weekend Retreat

The scenic shores of the Chesapeake Bay offer their own little world of tranquility and charm. Gentle waters lap rhythmically against the shore, and picturesque sunrises paint the sky with shades of pink, orange, and purple. It’s a landscape where forests and waterways weave together into a photographic backdrop for daily life. Chesapeake Bay town residents can enjoy all of this natural splendor while also feeling the warmth of tight-knit communities. If you’re looking for the perfect weekend retreat that blends incredible natural offerings and quirky small-town vibes, the towns surrounding Chesapeake Bay might be your perfect next adventure.

Cambridge, Maryland

Businesses along the main street in Cambridge, Maryland.
Businesses lined along the main street in Cambridge, Maryland. Editorial credit: 010110010101101 /

Nestled along the Choptank River, Cambridge is a delightful destination for a weekend retreat. This laid-back town offers a perfect mixture of outdoor features, historical landmarks, and culinary experiences. Nature lovers should not miss the Blackwater National Wildlife Refuge. Nicknamed the "Everglades of the North," this sprawling marshland sanctuary is perfect for birdwatching, photography, kayaking, and immersive hikes. The Choptank River is another natural gem. It doesn't matter if you're into fishing, boating, or simply want to enjoy a riverside picnic, the Choptank provides an opportunity for all of it. On the other hand, history buffs flock to the Harriet Tubman Underground Railroad Visitor Center, a museum that provides insights into the Underground Railroad. The knowledgeable staff can also direct you toward related nearby sites, such as meeting houses.

No matter how you spend your day, the night is sure to be fun, thanks to the town’s array of accommodation options. If you're looking for something ritzy, you might like the Hyatt Regency Chesapeake Bay. You'll find a golf course and spa at this upscale riverside marina. If you want a little more of a local experience, try Victoria Gardens Inn, a charming bed and breakfast built in a Victorian home.

Cape Charles, Virginia

Aerial view of Cape Charles along the coast of the Chesapeake Bay in Virginia.
Aerial view of Cape Charles along the Chesapeake Bay's shore in Virginia. Editorial credit: Kyle J Little /

This picturesque town on the Chesapeake Bay's eastern shore is quite small but packs a big punch. Cape Charles is a place of tight-knit community vibes, where events seem to be taking place year-round. Known as "Virginia's Cape," this town is encircled by stunning views and is home to a thriving small business scene. When planning a weekend jaunt to Cape Charles, be sure to check out The Northampton Hotel and Fig Street Inn, beautiful little bed and breakfasts that visitors consistently applaud. The Northampton Hotel offers views of the bay, including those memorable sunsets. Meanwhile, the Fig Street Inn might be a little smaller, but the hosts are beloved by locals and tourists alike.

Begin your visit with a stroll down Cape Charles Beach. This family-friendly spot is home to soft waves and a magnificent view. Catching a sunset over the Chesapeake Bay here is a requirement during any visitation. The next stop for outdoors enthusiasts is Kiptopeke State Park. Here, you'll find woodland walks that open onto a semi-secluded beach. This peaceful retreat caters to birdwatchers and nature photographers. After a day of sightseeing, beach hanging, and photo snapping, it'll be time to get some grub. Check out AJ's Bar & Grill, a hole-in-the-wall offering an array of perfected dishes.

Havre de Grace, Maryland

A historic lighthouse in Havre de Grace, Maryland.
The Concord Point Light lighthouse in Havre de Grace, Maryland.

After Cape Charles, visitors can head back to Maryland and stop in the magical town of Havre de Grace, a riverside jewel at the far northern end of the Chesapeake Bay. This special place rests at the point where the Susquehanna River flows into the bay, making it a unique and vibrant stop for outdoor enthusiasts. To this end, the Havre de Grace Promenade is a must for anyone interested in natural sights and a relaxing stroll. This promenade is a picturesque boardwalk that takes visitors along the waterfront, offering memorable views of the river and bay. For a more immersive experience, the nearby Susquehanna State Park is full of wildflowers, birds fishing in rivers, and cozy woodland hikes.

On the other hand, visitors interested in history should visit the Concord Point Lighthouse, one of the oldest continuously operating lighthouses in the United States. The nearby Keeper’s House Museum offers interesting information on past lighthouse keepers and the town's history and region. Another key stop is the Havre de Grace Maritime Museum, conveniently located within walking distance of the lighthouse.

In terms of finding a place to rest your head, check out the Vandiver Inn, a charming bed and breakfast known for world-class service. Another fun option is The White House of Havre de Grace, a guest house close to the Susquehanna that offers total privacy, a full kitchen, and a queen-sized bed.

Easton, Maryland

Buildings along Washington Street in Easton, Maryland.
Businesses such as the Scossa Restaurant along Washington Street in Easton, Maryland. Editorial credit: JE Dean /

Easton is a quaint small town located at the far northern end of the Tred Avon River. Home to 17,000 people, it offers a charming mix between small-town and urban center. One interesting thing to note is that Easton is only about a 25-minute drive from Cambridge, making it possible to incorporate both towns into a single weekend excursion. If you're looking to spend a night or two in Easton proper, the two establishments you should be sure to look into are the Hummingbird Inn and The Yellow Rose of Talbot. The Hummingbird Inn has the perk of being centrally located while still feeling off the beaten path. Meanwhile, the Yellow Rose of Talbot is a bit cheaper but also boasts great breakfast, quaint rooms, and surrounding grounds.

A short 15-minute drive north of Easton lies the Pickering Creek Audubon Center, a 450-acre working farm and sanctuary turned into a haven for birdwatchers and nature enthusiasts. It's a nice place to walk, sit, and enjoy a well-preserved piece of nature and spot birds such as Bobolinks and Bald eagles. Similarly, Tuckahoe State Park is another perfect place for nature lovers within a 25-minute drive. Here, you'll find a tranquil lake, winding trails, an arboretum, and even an aviary with owls.

Onancock, Virginia

View of Market Street in Onancock, Virginia.
View of the quaint Market Street in Onancock, Virginia. Editorial credit: John Blottman /

Onancock is a tiny, arty-crafty town situated on Onancock Creek. The "Creek" is a bit of a misnomer since this body of water is more of a river and eventually leads back to the Chesapeake Bay. In terms of sleeping arrangements in Onancock, visitors should look into the highly respected Inn at Onancock. They have unique and comfortable rooms, and the inn sits on beautifully manicured grounds. Another option worth considering is The Charlotte Hotel and Restaurant, especially for those who want to meet new friends. The restaurant and bar are often lively, and travelers from various parts of the United States pass through.

Although this eastern shore town is quite small, it is very lively and full of exciting stuff to do. On Market and North Streets, there are plenty of boutique shops and galleries that will ignite the inner artisan. Each outlet is unique, from the Crockett Gallery, showcasing beautiful watercolors and acrylics, to Marker 29 Design, specializing in cool crafts like embroidery and rhinestones. The town also has a thriving culinary scene. For your seafood needs, check out Mallards At the Wharf, where they serve crab cakes, mahi-mahi, linguine & claims, and much more. Or, if you're looking for something fancy, give Maurice a try, where you'll find entrees like Thai Chicken Cordon Bleu, Panned Barramundi, and plenty of creative, fresh sushi rolls.

Urbanna, Virginia

View of a boat along Urbanna Creek in Virginia.
A boat docked along Urbanna Creek in Urbanna, Virginia. By C Watts - Urbanna Creek, Urbanna Virginia, CC BY 2.0, Wikimedia Commons.

On the banks of the Rappahannock River sits Urbanna, an inviting Virginia town perfect for a weekend getaway. Down at the Urbanna Town Marina, visitors can head out for great creek and river exploration journeys through Urbanna and the surrounding areas. If you paddle inland from the Marina, you can follow Urbanna Creek into Town Bridge Pond, a serene waterway ideal for exercising while exploring.

Back in town, history enthusiasts flock to the colonial-era Christ Church, built in the 1720s. It's been exquisitely preserved and gives visitors a fascinating look at early American architecture and religious history. The peaceful churchyard is filled with a very old graveyard, offering an interesting moment to reflect and peruse the past. As for accommodation, the town has plenty of options, such as the serene Chesapeake Inn and the scenic Minnow apartment rental.

St. Mary's City, Maryland

A Colonial ship along the coast at St. Mary's City, Maryland.
A Colonial ship on display at St John's Site Museum in St. Mary's City in Maryland. Editorial credit: Regine Poirier /

St. Mary's City is a unique destination on this list, especially for history enthusiasts. It's a well-maintained colonial town with living actors open for historical visits and tours. In fact, the National Park Service has stated that it's probably the most intact 17th-century English town in the United States today. St. Mary's City offers immersive and interactive exhibits in its restored Town Center, Brick Chapel, and Godiah Spray Tobacco Plantation.

Most tourists opt to make Lexington Park their home base, as it's a quick 15-minute drive north. The area has a good range of accommodations, including the Comfort Inn & Suites and the Home2 Suites by Hilton. There are also plenty of food options in Lexington Park, with the town offering quite a range of global cuisine options. But if you're looking for something a little more picturesque, steeped in nature, and homey, you can head about 15 minutes south of St. Mary's City to find a couple of fantastic options. Look into the Swanendele Inn, a gorgeous bed and breakfast on the eastern side of the peninsula, and Pier450, a sleepy boutique motel that visitors consider a hidden gem.


The Chesapeake Bay area offers some of the quaintest and most charming small towns in the northeastern United States. This is a land of magical natural settings where visitors can leisurely stroll and relax or actively birdwatch or bike. These seven towns are all great options for a memorable weekend retreat, though everyone has their own preferences. Some might go to Cambridge to discover insights into the Underground Railroad and taste fresh-caught snow crab. Others may prefer to spend a magical few days in Havre de Grace walking the promenade and feasting on some of the northeast's most flavorful empanadas. Or, if you've got an insatiable historical curiosity, you could opt for an unparalleled journey into the past at St. Mary's City.

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