8 Romantic Small Towns In Maryland For A 3-Day Weekend
Couples are always looking for a place that feels like a true getaway without turning into a production. It has to be close enough to arrive relaxed, small enough to stay connected, and interesting enough that three days does not feel like a regrettable commitment. Maryland excels at this.
Its small towns lean romantic in practical ways, with walkable streets, water you can reach without driving, and hotels designed for intimacy. They are also fairly diverse in terms of budget. You can be pampered at lavish inns in Saint Michaels or pare things back and focus on the small details at bed and breakfasts in Berlin. No matter what an ideal long weekend looks like, Maryland offers options that make a three-day escape feel manageable and unforced.
Saint Michaels
The Inn at Perry Cabin rests directly on the Miles River, and that waterfront calm is one reason Saint Michaels was the filming location for the wedding reception scene at the Inn at Perry Cabin in Wedding Crashers. The property reflects Eastern Shore luxury, with wide lawns that meet the harbor. There is enough in Saint Michaels to fill a weekend, but the Inn also makes staying in feel complete. Fireplace suites, the Stars restaurant, the spa, and sailing Maryland waters aboard one of the property’s boats all contribute to the experience.
If the higher-end options are not of interest or not within budget, there are many quieter ways to enjoy the town itself. These include strolling along Talbot Street, stopping at Saint Michaels Winery, or spending time at Waterfront Park. The town’s dining scene is well established, with restaurants that make planning meals a central part of a three-day stay.
Havre De Grace
Havre de Grace sits where the Susquehanna River meets the upper Chesapeake Bay, and the town’s layout works well for a long weekend built around spending time outdoors together. The waterfront edge is narrow and linear, with a promenade that runs past Concord Point Park to the Concord Point Lighthouse. The lighthouse is a 19th-century structure, now operating as a museum, at the river mouth that locals pass on morning walks and evening loops.
Downtown runs parallel to the river, with St. John Street and North Washington Street holding most of the town’s dining and evening activity. This layout keeps everything walkable after dark. One of the more relaxed stops is The Vineyard Wine Bar, located a few shops away from Les Petits Bisous, a dessert spot suited to a morning or afternoon break. All of this is within walking distance of The Vandiver Inn, a historic bed and breakfast with a large veranda and stately rooms. For time on the water without leaving town, Sailing Sur le Vent departs from the harbor for daytime and sunset sails within the bay.
Berlin
The Inn Berlin sets the tone for a romantic three-day weekend immediately. It is a restored Victorian estate more than two centuries old, positioned on a small rise within the town of Berlin. The inn has five guest rooms, each with a private bath, along with a breakfast that supports slow, unhurried mornings. While it is closed from Christmas to early February, it remains a dependable option for a couple’s getaway throughout the year.
A weekend stay may align with Oktoberfest or the summer Peach Festival, or it may simply center on wandering a compact and historic Main Street. Nineteenth-century storefronts line the street, with the Calvin B. Taylor House museum and restaurants such as The Sterling Tavern offering easy ways to spend an afternoon. The same is true for time spent outdoors, including walks at Assateague Island National Seashore or along the former Bay Club Golf Course, which now features walking trails.
North Beach
North Beach runs along the western shore of Maryland’s Chesapeake Bay and was built as an early 20th-century resort town. It features a narrow beach and a boardwalk that passes directly along the sand and seasonal events such as Movies on the Beach. The free screenings at the water’s edge are one of several relaxed date options available over the course of a weekend.
A few blocks inland, the Mark R. Frazer Sunrise Garden fits ponds, rain gardens, and waterfalls into a single city block, creating a slow, looping walking path. Just south of North Beach, the Inn at Herrington Harbour offers water-view rooms, its own beach access, and an on-site restaurant. The property also includes a two-mile trail that connects gardens, marina slips, and shoreline, making it well-suited for a quiet morning walk after dinner at City Sliders Steakhouse.
Oxford
Rooms at the circa 1710 Robert Morris Inn help establish the tone of a romantic escape in Oxford, with working fireplaces, a modern British dining program, and views of the Tred Avon River. The town’s brick sidewalks lead past restored 19th- and 20th-century homes, along with hand-painted picket fences and small waterfront paths.
A scoop from Scottish Highland Creamery pairs easily with a walk toward Town Creek, time spent in Oxford Conservation Park, or a short ride on the Oxford-Bellevue Ferry. This is not the more polished setting found in nearby Saint Michaels. Instead, Oxford’s appeal comes from its long history and slower pace, which give the town a distinctly personal feel over the course of a long weekend.
Chesapeake City
Romance in Chesapeake City comes from water moving along the edge of its 19th-century streets, from sitting together in a RummuR Lounge while cargo ships pass beneath the Chesapeake City bridge, and from staying in a Victorian suite with the canal stretching beyond the windows. The Inn at the Canal delivers this setting with seven rooms and a Rum Lounge suited to quiet evenings as the sun drops behind the Back Creek Basin.
Outside, couples can walk sections of the Ben Cardin C&D Canal Trail, spend time in Pell Gardens Park, or take kayaks into the surrounding creeks. South Chesapeake City’s brick streets lead past antique shops, cafes, and small galleries. Seasonal events such as the Candlelight House Tour or June’s Canal Days can shape a three-day stay around the town’s historic waterfront.
Chestertown
Timing a three-day stay in Chestertown around the Chestertown Tea Party Festival places visitors in the middle of streets filled with colonial reenactments, craft vendors, and activity centered on Wilmer Park. The town lends itself well to a weekend shaped by history and shared routines.
The White Swan Tavern offers six guest rooms that balance historic character with modern comfort, including working fireplaces and river views. From there, couples can spend time walking the town’s brick-lined streets, stopping at Evergrain Bread Company, or heading out onto the Chester River. Options on the water range from quiet paddling through inlets to cruises operated by the Chester River Packet Company.
Easton
Easton's streets are lined with Colonial- and Victorian-era buildings that continue to serve everyday uses, which contributes to the town’s appeal for a relaxed weekend. Spending time together along North Washington or Goldsborough Street is an easy way to get a feel for downtown. The town hosts several annual events suited to couples, including October’s Waterfowl Festival and guided ghost tours offered at different points in the year.
The Avalon Theatre, a restored 1920s vaudeville house, operates year-round in the center of downtown and draws a steady calendar of concerts and performances. The Tidewater Inn offers a comfortable base for the weekend, with Hunter’s Tavern on site and close proximity to shops and restaurants. Easton is also near more than 4,000 acres of conservation land, including Pickering Creek Audubon, where couples can walk trails through wetlands and hardwood forests.
Why These Towns Work for a Three-Day Escape
A romantic three-day weekend works best when nothing feels forced. These Maryland towns allow couples to settle into shared routines quickly, whether through morning walks, long meals, or familiar streets by the second day. Places such as Chestertown and Oxford make this transition easy, while higher-end stays like The Inn at Perry Cabin in Saint Michaels still support a quieter, more personal pace.
Each of these towns suits a three-day stay because they reduce logistical friction and emphasize time spent together. With walkable centers, accessible waterfronts, and accommodations designed for shorter escapes, they offer couples a setting that feels distinct without requiring extensive planning.
