7 Ideal Maryland Destinations for a 3-Day Weekend in 2025

Maryland is often called “America in Miniature” because within its borders you’ll find the Atlantic Ocean shoreline at Ocean City, the forested ridges of the Appalachian Mountains in the west, fertile farmland stretching through central counties, and preserved historic towns along the Chesapeake Bay. This range of landscapes sits within a state that is only about 250 miles long, making it possible to reach beaches, mountains, and cultural centers all within a few hours’ drive.

Exploring Maryland destinations for a 3-day weekend in 2025 means seeing communities that balance history with everyday life. Places like St. Michaels, Chestertown, and Oxford reflect centuries of maritime and colonial history in preserved streets and active ports. Together, these towns show why Maryland stands out in the United States as a place where history, culture, and nature are accessible without long travel times. For 2025, these seven destinations are ideal bases for 3 days of discovery.

Chestertown

Chestertown is a riverside college town on Maryland’s Eastern Shore, where friendly faces and quiet streets make a three-day weekend feel like visiting old friends. Out on the water, Wilmer Park, right along the Chester River on South Cross Street, offers a kayak launch, picnic tables, a pavilion, benches, and wide open grass where locals walk dogs, gather for outdoor theatre, or bring lunches. Just off the park is the Wayne Gilchrest Trail, a paved 2.1-mile multi-use rail-trail that connects Wilmer Park to Gateway Park and winds past parts of the Washington College campus; biking or walking here gives both river views and a sense of town history when you pass the restored train depot where freight and passengers once arrived.

Every Saturday, the Chestertown Farmers & Artisans Market on Park Row fills the air with baked goods, fresh produce, crafts, and cheerful conversations with growers and artists. Accommodations add to the feeling of welcome: The White Swan Tavern provides a stay inside an 18th-century inn, giving you creaking floorboards, hearty breakfasts, and being right in the thick of town life.

St Michaels

St. Michaels sits along the Miles River and welcomes visitors with a rhythm that feels unhurried and familiar. A good starting point for the weekend is the Chesapeake Bay Maritime Museum, an 18-acre waterfront campus where you can step into the Hooper Strait Lighthouse, watch boatbuilders in the working shipyard, and explore collections that explain how watermen shaped this region. Just outside town, paddlers can rent kayaks or paddleboards from Shore Pedal & Paddle and slip into San Domingo Creek or Oak Creek, where the marshes are quiet and blue herons are often in view.

Back in town, Talbot Street’s galleries, boutiques, and specialty food shops give the feel of a community where shopkeepers strike up conversations rather than push sales, and places like the Crab Claw restaurant serve steamed crabs in a casual setting that hasn’t changed much in decades. The Inn at Perry Cabin offers waterfront suites, spa treatments, and complimentary bikes and kayaks for those who want comfort close to town.

Easton

Easton is best known for the Waterfowl Festival, a 50-year tradition that turns the town into a showcase for art, wildlife, and community. In the heart of town, the Academy Art Museum on South Street showcases more than 1,400 works in a renovated schoolhouse with a glass atrium, plus rotating exhibitions and art education programs that locals frequent and visitors enjoy. Riding and walking through the Easton Historic District (nearly 900 historic buildings) reveals colonial, Federal, Victorian architecture, restored homes, churches, and gardens, streets lined with bricks, and shaded by mature trees.

For a quieter spot, Trinity Cathedral is a Gothic Revival structure, finished in 1894 with stained glass windows and granite work, part of Easton’s spiritual and architectural fabric. Staying in Easton adds to the feeling of ease. The Tidewater Inn, steps from the Avalon Theatre and downtown shopping, offers restored rooms and suites, traditional décor, service that feels personal, and an on-site restaurant (Hunters’ Tavern) that draws both visitors and townsfolk.

Oxford

Oxford is a small waterfront town from the 1680s that feels like a well-kept secret. One of the most enduring draws is the Oxford-Bellevue Ferry, which has been operating since 1683. The short 7-10 minute crossing over the Tred Avon River delivers beautiful views of sailboats and riverbanks, and services both cars and bikes, perfect for a late-afternoon return after exploring Bellevue. The Oxford Museum, in the historic district on South Morris Street, keeps over 2,500 artifacts from colonial times to modern day. These include old tools from watermen, photographs, boat-building models, maritime memorabilia, and furniture donated by town families, which together tell the town’s evolution.

For nature lovers, Conservation Park, an 86-acre wetland area just off State Route 333, has walking and cycling trails, viewing areas for wildlife (herons and marsh birds), and quiet spots to watch sunrise or sunset. The Sandaway Suites & Beach, with about 18 suites and a private sandy beach, is ideal for relaxing.

Cambridge

Cambridge anchors the Choptank River with a working waterfront where skipjacks like the Nathan of Dorchester still sail, connecting visitors to Maryland’s maritime traditions. A few miles south, the Blackwater National Wildlife Refuge, around 25,000-29,000 acres of tidal marsh, freshwater lakes, forest, and open field, with hiking trails (5+ miles), paddling paths (often rented locally via Blackwater Adventures), and year-round bird-watching (bald eagles, migratory waterfowl). On the waterfront, Long Wharf Park gives picnic tables, benches, views of the skipjack Nathan of Dorchester (which has public sails in summer), and a replica Choptank River Lighthouse (this screwpile-style light has a small museum inside, open seasonally), which frames the river when water and sky glow.

The Dorchester Center for the Arts helps nurture the creative side of Cambridge with classes, seasonal exhibits, and performances, many hosted right in renovated storefronts downtown. Finally, Cambridge House Bed & Breakfast (112 High Street) is a Victorian-era inn within walking distance of the waterfront and downtown, serving good breakfast and personal service.

Solomons Island

Solomons Island, at the meeting point of the Patuxent River and Chesapeake Bay, feels like a living maritime postcard. The Calvert Marine Museum tells the story of local maritime history and estuarine ecology. You’ll see the historic Drum Point Lighthouse, the William B. Tennison vessel, interactive exhibits about oysters and bay life, and a river otter habitat. It’s central, so spending 2-3 hours here gives both education and lovely waterfront views. Solomon's Boat Ramp and Fishing Pier gives access for kayaks, canoes, SUPs, or launching small boats. Even if you’re not bringing your own gear, local rentals (Solomons Boat Rental, Bunky’s Charter Boats) have pontoons, kayaks, and jet skis.

History lovers will want the J. C. Lore Oyster House, now part of the museum complex, which preserves original oyster packing plant structure and shows the region’s seafood packing legacy. You’ll feel at home at the centrally-located Solomons Inn Resort + Marina, featuring an in-house pool and pet-friendly accommodations.

Bel Air

Known locally as the ‘Heart of Harford,’ Bel Air stands out as a town that holds on to kindness. One walkable highlight is the Historic Walking Tour (1.8- to 2.3-mile routes) through downtown. The tour shows 50+ historic buildings, homes, and churches, each with plaques telling who built them and how the town grew. It takes about 45-60 minutes. The Ma & Pa Heritage Trail stretches about 6.25 miles, linking Williams Street in downtown to Friends Park and Forest Hill. Along that trail, you cross bridges, go over overlooks, and see wooded creek valleys. It is easy to bike or walk.

Bel Air also often hosts the Summer Concert Series in Shamrock Park, plus movie nights in the park during warm months, which bring people together with food trucks, blankets, and local bands. Candlewood Suites Aberdeen-Bel Air features more space (suites), kitchenettes in rooms, which helps if you want to rest in or cook a light meal; it is still close enough to shops and restaurants.

Planning short getaways is often about access, variety, and a strong sense of place. The towns highlighted here show why Maryland destinations for a 3-Day weekend in 2025 are more than convenient; they are deeply rewarding. St. Michaels and Oxford reflect the state’s maritime history through working harbors and local seafood traditions. Easton and Chestertown sustain nationally recognized arts festivals and historic architecture that date back to the colonial era. Together, these towns make clear that Maryland is not just a corridor between major cities in the United States.