7 Perfect Destinations For A Long Weekend In Chesapeake Bay

Framed by winding two-lane roads, broad tidal rivers, and small towns that still move at a much saner pace, Chesapeake Bay is tailor-made for a long weekend escape. From the lively colonial streets of Annapolis to the hushed, dreamy waterfronts of Oxford and St. Michaels, the region offers a rare mix of rich history, gasp-inducing outdoor scenery, and easygoing charm. Places like North Beach and Havre de Grace reward travelers with walkable main streets, maritime heritage, and memorable sunsets over the water. Add in the slower, rural rhythms of the surrounding countryside, the beautiful boardwalks, and the soft, soothing atmosphere, and you have the perfect setting for a long weekend. Continue reading to discover seven perfect destinations for a long weekend in Chesapeake Bay.

St. Michaels, Maryland

St. Michaels is a classic Eastern Shore harbour town right on the Bay with a beautiful park by the water and an awesome maritime museum that houses the largest Chesapeake Bay watercraft in existence. Guests at the nationally famous Chesapeake Bay Maritime Museum can view more than 100 boats and boat models, historical Bay artefacts telling eye-opening stories about the area, and interesting artworks that include an impressive collection of watercolours, decoys, guns, and ship’s signboards.

Many locals will suggest that you find a parking lot and wander through the town's walkable core, stopping at Justine's Ice Cream Parlour for creative shakes and sundaes (it closes in winter), going to the Inn at Perry Cabin for a spa treatment, or sampling a plate of bread pudding with homemade butterscotch at Bistro St. Michaels, a favourite eatery on Talbot Street providing gluten-free options in a romantic setting. For an extended adventure, consider taking the ferry from Bellevue over to Oxford. Otherwise, places like the Classic Motor Museum of St. Michaels, with its nice collection of classic cars, are enjoyable diversions. For spending the night, the Inn at Perry Cabin is an upscale beauty in a colonial-style property.

North Beach, Maryland

North Beach sits directly on the western shore of the Bay and has a neat, sandy beach, a beautiful pier, and a half-mile boardwalk offering a bike path, benches (to sit and dream), and soothing views over the Chesapeake Bay. Expect seven blocks of waterfront, a variety of shops, including antiques and gifts, and a decent number of restaurants serving fresh seafood and other tongue-tingling delicacies. Nice & Fleazy Antiques on Bay Avenue has interesting wall art for sale, while Lighthouse Market & Signs has decently priced souvenirs and an impressive collection of kids' toys and gifts.

Stroll down to Mark R. Frazer Sunrise Garden, where you will admire beautiful sculptures and landscaping, as well as quiet ponds with koi fish. After basking in the salt-tinged air and exploring the 30,000-square-foot parcel, head to North Beach Pier, known for some of the most amazing sunrises and sunsets in the region. It also offers excellent fishing opportunities, especially in the fall and winter months. If spending the night, Bayfront Home with Amazing Rooftop Deck is a comfortable vacation rental with lovely water views and personable hosts

Oxford, Maryland

Travel back in time as you walk along Oxford's tree-lined streets with charming historic homes, beautiful picket fences, and well-preserved 18th-century architecture, including the Robert Morris Inn, touted as the oldest full-service inn in America. The inn is set in a historic home built in 1710 and is just across the road from the ferry terminal. You may already know that the Oxford-Bellevue Ferry, which offers a scenic ride across the gentle Tred Avon River, is one of the oldest privately owned ferries in the U.S. Similarly, Oxford, founded almost a century before the Declaration of Independence, is among America’s oldest towns.

The town is directly on the Bay and bustles with unique shops, inns and taverns, and fabulous water views. History nerds will get a blast at the well-curated Oxford Museum, which displays memorabilia chronicling more than three centuries of Oxford’s Colonial and American history. Start your day with a pumpkin-spiced latte at the highly rated Oxford Social Cafe, then follow it up with a visit to the Scottish Highland Creamery, one of the country's best homemade ice cream stands. Note that Sandaway Suites & Beach offers comfortable cottages and soft, waterfront views, making it an ideal place to stay.

Irvington, Virginia

Whether you want to spend a memorable afternoon onboard a bird-watching cruise, mingling with ospreys, eagles, and nesting herons, or feast on fresh seafood and bright cocktails at The Dredge, a vibrant spot run by a culinary hero and famous chef with more than 25 years of experience, including stints at Key West, Irvington is an enjoyable vacation spot with a full tray of interesting delights. A sleepy little village with fewer than 1,000 residents, Irvington is emerging as a sought-after foodie destination, particularly for visitors exploring Virginia's coastal region. There's Hope and Glory Inn, a hopelessly romantic boutique hotel housed in a renovated 1890s schoolhouse, offering a delightful flight of flavours, a hip pool, and lush English gardens with meandering brick pathways. One of the inn’s highlights is “Garden Bath,” an outdoor shower enclosed by an 8-foot fence that includes antique mirrors, a claw-foot tub, and a rainforest shower.

Otherwise, fill your soul with bright colours and incredible art pieces at Objects Art and More, then amble through the Steamboat Era Museum (it closes in winter), which displays beautifully rendered exhibits focused on Bay-based transportation when the steamboats chugged along the Chesapeake. Spend the night at Tides Inn, which has a lovely walking trail that wraps around the property and that is often ideal for sunset strolls.

Havre de Grace, Maryland

Lovers of American history will relish spending a weekend in a town that narrowly missed becoming the capital of the United States. Positioned right where the Susquehanna River empties into the Bay, Havre de Grace is rich with historical undertones, reflected in its preserved architecture, waterfront promenades, and historical touchpoints. You can explore the Lock House Museum's rich canal history, learning about life in the mid-1800s along the Susquehanna and Tidewater Canal, catch a glimpse of the Concord Point Lighthouse, which is the second-oldest lighthouse in Maryland, or spend time at the Havre de Grace Decoy Museum, which houses one of the finest collections of decorative Chesapeake Bay decoys ever assembled. Crown the day with decadent crab cakes at Tidewater Grille, then lay your head at Vandiver Inn, a charming Victorian-style B&B set over 3 houses.

Easton, Maryland

Easton, one of Maryland’s official Arts & Entertainment Districts, is on the Miles River, which flows into the Chesapeake Bay. Consequently, the town is big on art and offers an interesting mix of galleries, theatres, museums, and studios that attract both local and visiting artists. Plein Air Easton, held over 10 days each July, is the largest and most prestigious juried plein air painting competition in the United States. If you can’t wait till July, visit Avalon Theatre, widely considered “The Eastern Shore’s Most Beautiful Show Place.” The theatre has been the town’s cultural heartbeat for more than 100 years and is regarded as one of America’s finest Art Deco theatres still in operation. Meanwhile, at the Academy Art Museum, one can admire world-class art free of charge, whether in prints, paintings, sculpture, or digital media. Spend a quiet night at Best Western Plus Easton Inn & Suites, conveniently located off Highway 50 on the way to Cambridge.

Annapolis, Maryland

Annapolis, whose unique design is reminiscent of an old European town, an aspect that sets it apart from most U.S. capitals, is a vibrant destination with one of the most walkable downtowns. Maryland State House, which holds the distinction of being the nation's oldest state house in continuous legislative use, briefly served as the nation’s capital in the 1780s. Its large wooden dome is a 94-foot masterpiece billed as the largest all-wooden dome in North America, built entirely without nails. A short walk down Maryland Avenue leads to the U.S. Naval Academy Museum, which houses one of the world's most extensive collections of ship models and rare maritime artefacts.

Restaurants have side-street patios ideal for outdoor dining, especially when the weather is great, while antique stores offer furniture, beautiful home décor items, interesting collectables, and vintage maritime pieces. Maryland Avenue is particularly an antique lover's dream, especially with places like Evergreen Antiques and True Vintage, a downtown mainstay since 2001. Spend the night at Inn on Main, which is within walking distance of almost everything you need.

So, whether you finally want to experience one of America’s oldest ferry crossings or stroll down lively waterfront promenades with terrific views on almost every side, the Chesapeake Bay ticks every box. Think of lively antique-lined streets, refined outdoor dining, sometimes on shaded side-street patios, bird-watching cruises, and romantic inns set amid lush, rustic gardens; a weekend here will turn out to be memorably therapeutic. There's history. There are sandy beaches with swinging hammocks. There are also many cultural attractions, including historic theatres and cute art galleries displaying beautiful artwork from local artists. Whatever one's schedule, the Bay is calling.