8 Best Chesapeake Bay Towns For A Weekend Trip
Situated in the Mid-Atlantic region, Chesapeake Bay is the largest estuary in the United States. It extends throughout six states, including Maryland, Virginia, West Virginia, Delaware, Pennsylvania, and New York. While the area is known for its extensive habitat, the region also offers numerous charming retreats that make for the perfect weekend getaway. Whether you're looking for an escape from the city or want to discover a new classic small town in Chesapeake Bay, the region has just about everything you need for some time off.
These towns are full of historic landmarks, cultural museums, and coastal resorts that will make your weekend away memorable and relaxing. No matter if you're keen to partake in outdoor adventures like hiking or sailing, or you're looking to spend some time at the spa right off the coast, Chesapeake Bay is home to it all. These eight towns are not only full of small-town charm but also brimming with the Chesapeake Bay spirit that's perfect for a fun weekend of exploration, relaxation, and discovery.
Saint Michaels, Maryland
Saint Michaels is a quintessential Chesapeake Bay getaway, often referred to as “the town that fooled the British” for its clever War of 1812 history. Its historic harbor and colonial buildings give it a timeless charm, while Talbot Street serves as the heart of downtown with art galleries, boutiques, and seafood restaurants. The Chesapeake Bay Maritime Museum is a highlight, offering an in-depth look at the region’s nautical heritage and views across the water.
For accommodations, the Inn at Perry Cabin offers a luxurious retreat, complete with a spa and sailing excursions. Outdoor enthusiasts can rent kayaks or enjoy harbor cruises, while food lovers will appreciate local crab houses like The Crab Claw Restaurant, which offers award-winning crab cakes and more. Saint Michaels’ ability to blend waterfront adventure, historic intrigue, and upscale leisure makes it a beloved spot for both weekend visitors and long-term admirers of Chesapeake living.
Oxford, Maryland
One of Maryland’s oldest towns, Oxford was founded in the 1600s and retains an unhurried pace that sets it apart from busier Bay destinations. Downtown streets are lined with historic homes and shaded by leafy trees, creating an inviting setting for walks or bike rides. The Oxford Museum details the area’s maritime past, while the Oxford-Bellevue Ferry—in service since 1683—offers a scenic connection to St. Michaels.
Food and drink are central to the town’s charm, from waterfront dining at Doc's Sunset Grille to the renowned ice cream at Scottish Highland Creamery. The Oxford Inn offers cozy accommodations close to the shoreline, making it an ideal spot for a quiet retreat. Whether you’re relaxing at the marina, exploring preserved architecture, or enjoying a sunset over the Tred Avon River, Oxford promises a peaceful Chesapeake experience.
Annapolis, Maryland
Though it serves as Maryland’s capital, Annapolis retains a warm, small-town feel with a lively waterfront downtown. The city’s history shines at the Maryland State House, the oldest U.S. state capitol still in legislative use, while the nearby U.S. Naval Academy offers fascinating tours. Downtown Main Street is bustling with boutiques, antique shops, and restaurants, many of which overlook the scenic harbor.
Seafood lovers flock to Cantler’s Riverside Inn, famous for steamed crabs, while boat tours provide unforgettable views of the Chesapeake. For a refined stay, the Annapolis Waterfront Hotel offers rooms overlooking the marina. The city’s blend of maritime culture, history, and modern amenities makes it a vibrant weekend destination. With its sailing community and lively events calendar, Annapolis offers energy and charm in equal measure.
Cape Charles, Virginia
Cape Charles is a historic seaside town on Virginia’s Eastern Shore, known for its pristine sandy beach and restored Victorian architecture. The Cape Charles Historic District preserves the town’s early 20th-century charm, while downtown streets are lined with boutiques, cafés, and antique shops. Outdoor enthusiasts can explore Kiptopeke State Park, a nearby coastal reserve that offers trails, fishing, and birdwatching opportunities.
The Hotel Cape Charles is situated in the heart of downtown and offers chic accommodations with a distinctly coastal feel. Visitors can sip wine at Chatham Vineyards or tee off at Bay Creek Resort’s golf courses, all within easy reach of town. Cape Charles’ welcoming community, combined with its mix of relaxation and recreation, makes it an appealing Chesapeake retreat with both history and modern amenities.
Rock Hall, Maryland
Nicknamed the “Pearl of the Chesapeake,” Rock Hall combines nautical charm with vibrant community spirit. Its historic downtown features art galleries, live music venues, and seafood restaurants that showcase the town’s creative side. The nearby Eastern Neck National Wildlife Refuge adds natural appeal with its bird-watching trails and sweeping views of the Bay.
Visitors can enjoy annual events, such as Pirates and Wenches Weekend, which transforms the town into a lively, themed festival that includes live music, vendors, and, of course, a treasure hunt. For accommodations, the Inn at Haven Harbour offers waterfront lodging with marina access. Rock Hall’s perfect balance of art, outdoor recreation, and nautical life makes it a beloved stop for those seeking Chesapeake authenticity in a laid-back setting.
Cambridge, Maryland
Cambridge has embraced revitalization while maintaining its heritage as one of the Bay’s oldest colonial towns. Its downtown features restored brick buildings now home to boutiques, craft breweries, and restaurants like The Dive Club. Visitors can learn about history with walking tours via the Harriet Tubman Museum and Educational Center, a tribute to one of the Eastern Shore’s most famous residents.
Nature enthusiasts will enjoy Blackwater National Wildlife Refuge, a short drive away, famous for its bald eagles and extensive wetlands. For accommodations, the Hyatt Regency Chesapeake Bay Golf Resort, Spa, and Marina offers luxury amenities and waterfront views. Cambridge’s mix of cultural history, outdoor adventure, and modern comforts makes it an excellent destination for a weekend in the Chesapeake Bay area.
Havre de Grace, Maryland
Perched at the top of the Bay where it meets the Susquehanna River, Havre de Grace is a small city with picturesque charm. Downtown highlights include the Concord Point Lighthouse and Keeper's House Museum, as well as antique shops and art galleries. A walk along the Havre de Grace Promenade provides sweeping water views, while the Decoy Museum celebrates the area’s unique duck-carving tradition.
The Vandiver Inn, a Victorian bed-and-breakfast, offers stylish accommodations in the heart of town. Meanwhile, outdoor enthusiasts can explore nearby Susquehanna State Park, which offers hiking, fishing, and camping opportunities. With its mix of history, culture, and waterfront scenery, Havre de Grace appeals to both day-trippers and weekend visitors seeking a cozy Chesapeake retreat.
Urbanna, Virginia
Urbanna may be small, but it has big character and is especially famous for its annual Oyster Festival, which draws thousands each November for live music, shucking competitions, and tons of other community events. The historic downtown features preserved colonial homes, small shops, and casual restaurants, all within walking distance of the water. Visitors can also explore the Urbanna Museum and Visitors Center in a restored 18th-century Scottish Factor Store or take a peaceful paddle along Urbanna Creek.
Bethpage Camp-Resort offers a family-friendly destination, featuring cabins, RV sites, and amenities located near the shoreline, while the Chesapeake Inn is a cute and cozy spot for accommodations right in town. For relaxation, Taber Park provides a quiet spot to enjoy the sun. Urbanna’s tight-knit community, combined with its oyster heritage and waterfront setting, makes it a cozy destination on the Chesapeake Bay, ideal for both food lovers and history buffs.
Exploring Chesapeake Bay
The Chesapeake Bay is home to towns that combine waterfront beauty, cultural richness, and welcoming communities, making them perfect weekend destinations. From the colonial history of St. Michaels and Oxford to the sandy beaches of Cape Charles and the vibrant sailing culture of Annapolis, each town offers something unique. Luxury resorts, historic inns, and family-friendly accommodations ensure a comfortable stay while exploring local museums, state parks, and harborfronts. What sets these destinations apart is their ability to strike a balance between relaxation, culture, and adventure. Whether you’re savoring seafood in Cambridge, birdwatching in Rock Hall, or attending a festival in Urbanna, these Chesapeake towns offer a little something for everyone. More than just quick getaways, they offer timeless escapes that keep visitors returning year after year.
