7 Picturesque Towns in Chesapeake Bay for a Weekend Retreat in 2024

The Chesapeake Bay region is known for its serene waters, abundant wildlife, and charming coastal towns. The states of Maryland and Virginia border the bay, and include a number of quaint and charming small towns. For those seeking a relaxing weekend retreat, the area offers several destinations with scenic views, vibrant cultures, and cozy accommodations. Whether it's historic streets, lush landscapes, or a taste of fresh seafood, these towns provide a perfect escape. From the artsy haven of St. Michaels to the quaint village of Oxford, the following towns offer a blend of natural beauty and small-town charm, making them ideal for a quick getaway or even a longer stay.

St. Michaels, Maryland

St. Michaels is renowned for its maritime history and picturesque harbor. Travelers can stroll down Talbot Street, lined with quaint shops, seafood restaurants, and local boutiques. Visit the Chesapeake Bay Maritime Museum to learn about the area’s seafaring past, including restored boats and lighthouse exhibits. Nature lovers can explore the beautiful Miles River by kayak, or take a scenic cruise to admire the coastline.

For those seeking a more leisurely activity, wine-tasting at the local wineries Like St. Michael’s Winery or Bordeleau Winery is also a popular option. The Inn at Perry Cabin, a luxurious waterfront resort, offers elegant rooms, a world-class spa, and beautiful gardens, making it a peaceful and romantic retreat. With its blend of history, art galleries, and easy access to the water, St. Michaels offers visitors a perfect mix of adventure and relaxation.

Oxford, Maryland

Not far from St. Michaels is Oxford, one of the oldest towns in Maryland. Oxford is a serene village known for its well-preserved colonial architecture and peaceful ambiance. Travelers can take the Oxford-Bellevue Ferry, one of the nation’s oldest still in operation, offering stunning views of the Tred Avon River and a quick connection to nearby towns like St. Michaels and Easton. The Oxford/St Michaels bike trail also runs between the two towns, covering nearly 30 miles of bike path.

In town, the Oxford Museum provides insight into the area’s rich maritime and cultural history, while waterfront parks and marinas offer scenic spots for picnicking and boating. Outdoor enthusiasts will enjoy kayaking through the peaceful creeks and coves that surround the town. Don’t miss The Robert Morris Inn, a historic hotel dating back to 1710. This oldest full-service Inn in America provides a cozy, waterfront stay with fine dining options that feature regional cuisine. Oxford’s slow pace and picturesque surroundings make it an idyllic retreat for those looking to escape the hustle and bustle.

Cambridge, Maryland

Another gorgeous Maryland town on the Chesapeake Bay is Cambrige. Cambridge boasts a charming downtown filled with historic architecture and vibrant street art. The town is also known for the Harriet Tubman Museum and Educational Center, a must-see for history buffs looking to learn about the famed abolitionist's life.

Just outside town, the Blackwater National Wildlife Refuge also known as the “Everglades of the North” offers vast marshlands perfect for birdwatching, hiking, and nature photography. Local restaurants along the scenic Choptank River serve up fresh seafood, giving visitors a taste of the region’s culinary heritage or try a local brew at RAR Brewing. The Hyatt Regency Chesapeake Bay is an excellent choice for accommodations, featuring golf courses, a marina, and a spa, making it ideal for travelers looking to unwind. For something a little quieter, opt for the Cambridge Bed and Breakfast.

Cape Charles, Virginia

Nestled on the Eastern Shore, Cape Charles offers stunning beaches, historic homes, and a variety of boutique shops and eateries. Visitors can relax on Cape Charles Beach, known for its calm, shallow waters, making it perfect for families with children. The town’s historic district is filled with restored Victorian homes, art galleries like the At Altitude aerial photography studio, cozy cafes, as well as the Historic Palace Theater and Cape Charles Memorial Library.

Grab a bite to eat at Mason Avenue Bakery, and Coastal Baking Co. or try some local libations at Cape Charles Brewing. For those interested in exploring the bay’s wildlife, Kiptopeke State Park offers hiking trails, fishing spots, and birdwatching. The Bay Haven Inn, a charming bed-and-breakfast known for its warm hospitality, beautiful gardens, and gourmet breakfasts, is an excellent choice for a comfortable stay.

Urbanna, Virginia

Famous for its annual Oyster Festival, Urbanna exudes maritime charm with a long-standing connection to the Chesapeake Bay’s rich oyster culture. Visitors can learn about the town’s history at the Urbanna Museum and Visitors Center, housed in a historic building that once served as a colonial tobacco warehouse. The historic district offers beautiful, well-preserved homes and a variety of restaurants like Little Jimmys, or pick up freshly caught oysters and other local delicacies at Shores and Ruark Seafood.

The nearby Bethpage Camp-Resort is a versatile accommodation option featuring a water park, mini-golf, and cozy cabins, making it a great family-friendly retreat. Those looking for a quieter experience can take a peaceful cruise along Urbanna Creek or stroll through the picturesque marina.

Rock Hall, Maryland

Known as the "Pearl of the Chesapeake," Rock Hall is a picturesque town with a deep maritime heritage that attracts sailors, boaters, and nature enthusiasts. Like Urbana, the town had several marinas and a gorgeous harbor. The marinas are perfect for sailing excursions, and visitors can rent boats or join guided fishing trips to explore the surrounding bay waters from vendors like Shardana Sailing Charters.

Rock Hall Beach offers a quiet spot for sunbathing and swimming, while Eastern Neck National Wildlife Refuge, just a short drive away, is ideal for hiking, birdwatching, and observing local wildlife. Haven Harbour Marina Resorts provide comfortable accommodations with easy access to pools, bike rentals, and waterfront activities, ensuring guests have a relaxing stay. Explore a traditional fishing shanty at the Rock Hall Waterman’s Museum, or learn about the town’s roots at The Rock Hall Museum. There is so much to see and do in this little maritime town.

Solomons Island, Maryland

Located at the mouth of the Patuxent River, Solomons Island is a vibrant town known for its cultural attractions and scenic beauty. The town is roughly an hour and a half drive from Washington D.C. and two hours from Baltimore, making it a great destination for a weekend retreat. The picturesque views start as visitors drive up to the island by way of the Governor Thomas Johnson Bridge, which offers impressive views of the town and surrounding islands.

The Calvert Marine Museum features local maritime history, interactive exhibits, and an iconic lighthouse that visitors can tour. Art lovers will enjoy the Annmarie Sculpture Garden & Arts Center, which hosts art exhibits, outdoor sculptures, and nature trails. The island is dotted with seafood restaurants, where diners can enjoy freshly caught crabs, oysters, and other local dishes while taking in views of the bay. The Solomons Victorian Inn, a charming and stylish bed-and-breakfast, provides a comfortable base for exploring the area, with elegant rooms and easy access to local attractions.

From the historic streets of Oxford to the sandy shores of Cape Charles, the Chesapeake Bay is home to some of the most picturesque and inviting towns on the East Coast. Each destination offers unique experiences, whether it’s indulging in fresh seafood, exploring rich local history, or simply enjoying the calming waters of the bay. With cozy accommodations and a mix of cultural and natural landmarks, these towns provide a perfect backdrop for a peaceful weekend retreat, and their charm makes them ideal spots for a longer, more permanent escape.