10 Amazing Weekend Getaways in Maryland for 2026
One of America’s smallest states, yet incredibly endowed with beauty and culture, Maryland is one of the top destinations for weekend getaways in 2026. Bordering the Atlantic Ocean, this state features everything from white sand beaches and old-growth forests to waterfalls, lakes, and mountains. And of course, the Chesapeake Bay looms large on the state’s Eastern shore, representing the largest estuary in the US. No wonder the state has earned the title America in Miniature.
Worth visiting individually on separate weekends in 2026, each of these towns comes with a slice of Maryland, from one hosting the state’s largest lake to another serving as the gateway to the state’s only Oceanfront park.
Easton
This peaceful town on the Eastern Shore is an ideal place to relax, recharge, and enjoy one of the most charming downtowns in Maryland. Located just an hour and 20 minutes from Washington D.C., the town welcomes travelers with adorable streets lined with trees and architecturally stunning structures. Weekend travelers are invited to stroll these streets to soak in the sights and explore local attractions, such as the family-owned Far Eastern Shore Winery, which features a good selection of fruit wine blends. Just a short walk from this winery, Doc’s Downtown Grille promises to leave lasting memories with its warm atmosphere and diverse menu, featuring seafood delights, like shrimp tacos and other American favorites, as well as wine, beer, and cocktails. Those who love to stay at historic properties will appreciate the Tidewater Inn, located right at the heart of downtown Easton. Established in 1949, this Colonial Revival brick hotel offers an unforgettable stay with well-equipped rooms adorned with traditional decor and furnishings, as well as notable amenities such as an on-site restaurant and bar, free parking, and a spa. As for those who love the arts, the Academy Art Museum is worth visiting to explore over 1,500 artworks, participate in art classes, or catch lectures and concerts.
Havre de Grace
Havre de Grace is the ideal town for a peaceful weekend getaway full of coastal scenery and adventures. Located on the Susquehanna River, where it empties into the Chesapeake Bay, the town boasts a couple of waterfront attractions, one of which is Friends-Concord Point Lighthouse. Weekend travelers will enjoy spending time at this historic lighthouse, which was built in 1827 and offers tours of its interior and the keepers' house, as well as the opportunity to climb to the top of the structure for breathtaking views of the river and the bay. Still on the waterfront, Havre de Grace Promenade offers a peaceful walk with picturesque bay and river scenery, plus it is adjacent to a couple of attractions, including Havre de Grace Maritime Museum, which features artifacts and exhibits highlighting the region’s maritime history.
Furthermore, several great restaurants sit on this town's waterfront, with the Tidewater Grill being one of the most popular. This restaurant is a must-visit on a weekend in this town for beautiful views and a wide variety of fresh seafood, steaks, and other American fare. And just outside town, the Susquehanna State Park will also delight weekend travelers as it offers fishing, boating, and camping opportunities, as well as 15 miles of trails for hiking, biking, and horseback riding. That said, a stay at the Vandiver Inn is recommended on a weekend getaway to Havre de Grace. Located within walking distance of the main street, this Victorian-style hotel features a beautiful garden, bar, free parking, and well-furnished, spacious rooms.
Annapolis
A weekend getaway can translate into a longer vacation or even residency in this charming town on the Chesapeake Bay. The capital of Maryland, the town blends big-city amenities with small-town charms, and is located around 45 minutes from both Washington, D.C., and Baltimore, making it easy to access. Here, weekend travelers will be met with an inexhaustible list of things to explore, from the Maryland State House, which is the oldest in the US in continuous legislative use, built in 1772, to the U.S Naval Academy Museum, which preserves and showcases the country’s long naval history. However, those who want a more exciting outdoor experience will be better served at one of the town’s waterfront parks, particularly the popular Sandy Point State Park. Situated right on the Chesapeake Bay, this park is a delightful place to be on a warm sunny weekend, with a spacious swimming beach and a marina offering boating services and launching ramps. Opportunities for fishing and crabbing also abound in the park, plus hikers have four miles of trails to explore and see native plants and animals.
In the meantime, the Boatyard Bar & Grill is always a great place in Annapolis to relax with delicious seafood and waterfront scenery. And for an enjoyable stay, weekend travelers are invited to the Graduate by Hilton Annapolis, which offers cozy, colorfully decorated rooms, alongside an on-site restaurant, a fitness center, and easy access to the pleasures of downtown Annapolis.
Boonsboro
Breathtaking mountain scenery and a peaceful ambience are the first things that weekend travelers to this town will enjoy, but there’s more. Positioned at the foot of the South Mountain, Boonsboro is a haven for nature-based endeavors, with the Crystal Grottoes Caverns to the west and Greenbrier State Park to the northeast. Both attractions are must-visits, with the Crystal Grottoes being the only commercial cave in Maryland, offering tours to see large caves full of unique formations, including stalactites and flowstone. At Greenbrier State Park, a 42-acre manmade lake sets the stage for swimming, canoeing, boating, and fishing. The park also boasts a white sandy beach, equipped campsites, and 11 miles of trails winding through a variety of habitats. More than the outdoor adventures, Boonsboro will delight weekend travelers with other draws, from the Boonsboro Antiques, with its wide selection of antiques and vintage items, to the Branded Chophouse, where attentive service meets delicious seafood, steak, and American fare. To the question of where to stay, Inn Boonsboro is a resounding answer. Situated at the heart of town, this bed and breakfast is located in a restored building dating to the 1790s, and it promises a comfortable experience, with its warm and well-equipped rooms, and amenities such as breakfast, a library, and a cozy lounge.
Ocean City
Beaches, endless entertainment, and world-class dining are all on the list of things to enjoy in Ocean City on a weekend getaway. The most popular coastal destination in Maryland, located right on the Atlantic Ocean, this town promises to leave lasting memories with a myriad of attractions, many of which sit right on the Ocean City Boardwalk. Walking on this three-mile boardwalk is therapeutic and a way to forget one’s worries while exploring fun draws like Ripley’s Believe It Or Not, a museum full of oddities, like two-headed animals, and facilities of illusion, including a mirror maze. Some of the town’s best hotels also sit on this boardwalk, including the Holiday Inn & Suites Ocean City by IHG, which features outdoor pools, on-site dining, and rooms with expansive ocean views. Meanwhile, the boardwalk borders the soft sand Ocean City Beach, which stretches 10 miles, and makes for the perfect place to spend quality time lazing, people watching, running barefoot, sunbathing, and swimming. For food lovers, Ocean City hosts some of the best restaurants in the country, including Seacrets, which serves Caribbean-inspired food and drinks often blended with live entertainment in an oceanfront setting.
Oakland
Travelers will wish weekends were longer in this adorable little town, often overlooked as it is populated by just 1,800 people and is located deep in Maryland’s western region near the border with West Virginia. A true hidden gem for a weekend getaway, Oakland is surrounded by beloved natural attractions, starting from Deep Creek Lake State Park. This park is a haven for adventures, featuring a mile-long shoreline on Maryland’s largest lake, which sets the stage for canoeing, boating, swimming, and fishing. On top of that, the park boasts over a hundred campsites, 20 miles of hiking and biking trails, and a variety of wildlife, including black bears.
A few miles west of this park, the Swallow Falls State Park is another incredible place brimming with breathtaking natural scenery and adventures. This park is defined by an old-growth forest bordered by the Youghiogheny River, which forms several waterfalls, including Muddy Creek Falls, Maryland’s highest free-falling waterfall at 53 feet. A mile-long trail offers access to those features, plus the park boasts dozens of campsites. In downtown Oakland, the Oakland B & O Railroad Museum will delight history buffs with local and regional railroad artifacts. Additionally, the highly-rated Oak Mar Motel sits right at the heart of town, offering a pleasant lodging experience with its air-conditioned rooms, free private parking, and an on-site restaurant.
St. Michaels
A weekend getaway in St. Michaels is a satisfying experience, even though it is one of the state’s smallest towns, with just a thousand residents. History buffs and coastal lovers will be especially thrilled here, as the town is on Maryland’s Eastern Shore and was established in the 1670s. Today, it hosts notable historic attractions, like the 1879 Hooper Straight Lighthouse, where one can learn about the risky seaside life of a lighthouse keeper from the 19th century. St. Michaels is also the proud home of the Chesapeake Bay Maritime Museum, an 18-acre waterfront museum featuring a diverse collection of artifacts, exhibits, and vessels highlighting the economic, natural, and cultural history of Chesapeake Bay, the third-largest estuary in the world. The museum also boasts a working shipyard and offers seasonal cruises aboard some of its historic vessels. Beyond the history, weekend travelers to St. Michaels will enjoy sampling over a dozen types of wines at the St. Michaels Winery, while the St. Michaels Harbour Inn will further make the weekend getaway unforgettable with its incredible features. Located on the harbor, this full-service resort offers more than just dozens of waterfront rooms and suites, but also an onsite spa and restaurant, an outdoor pool, and a marina with 57 boat slips.
Thurmont
Situated at the foothills of the Catoctin Mountain, near the border with Pennsylvania, this town is the perfect place to escape from it all and connect with nature. For starters, the town is laid-back with a population of around 6,200, and is surrounded by natural scenery and attractions, with the most popular being Cunningham Falls State Park. Covering an area of over 6,000 acres, this park is home to Maryland’s highest cascading waterfall and a network of trails winding through dense woodlands, including the 1.5-mile Cat Rock Trail, which leads to a rugged rock formation with scenic views. Additionally, the park boasts campsites and cabins, a lake with a sandy beach, and opportunities for swimming, fishing, and boating. Just north of this park, the Catoctin Mountain Park is another great spot to spend quality time in nature. This beautiful park in the Blue Ridge Mountains features streams for fishing, secluded campsites, and 25 miles of hiking trails with some leading to scenic vistas.
Elsewhere, the Catoctin Breeze Vineyard invites weekend travelers to unwind with delicious wine and picturesque mountain scenery. In the downtown area, one can further unwind by exploring some local establishments, such as the family-owned Thurmont Kountry Kitchen, which serves a variety of home-cooked meals, including broasted chicken. Meanwhile, the Inn at Springfield Manor is a great place to stay on a weekend getaway to Thurmont. Located just outside town, this hotel offers easy access to the area’s top draws, as well as adorable and airy rooms, free parking, and daily breakfast.
Berlin
A weekend getaway to Berlin is an opportunity to explore one of Maryland’s most appealing natural features, Assateague State Park. This attraction alone is worth a weekend in Berlin, as it boasts two miles of beaches open for swimming and surf fishing, as well as wildlife, including deer, waterfowl, and the famous Assateague wild horses. The park also features hundreds of campsites and a marina with a boat launch. Beyond the oceanfront park, Berlin’s Main Street will delight weekend travelers with its long line-up of local establishments, including Blacksmith, a cozy place to relax and refill with farm-to-table meals, cocktails, and beer. In the meantime, Ocean Downs Casino is just outside downtown Berlin and offers an incredibly exciting experience with over 800 slot machines and a wide variety of games, alongside diverse dining options, and a harness racetrack hosting live racing events in summer. For those who love being at the heart of it all, the Atlantic Hotel is a recommended place to stay while visiting Berlin. Located right on Main Street, this hotel is a short distance from the town’s top attractions, plus it features Victorian-era style rooms, free parking, porches with rocking chairs, and an on-site restaurant and bar.
Cumberland
Weekends at Cumberland promise to be fun, especially for those who love history and natural scenery. Once one of the largest cities in the state and a bustling manufacturing center that fueled the industrial revolution, this town now hosts the Allegany Museum, where weekend travelers spend quality time learning about the past. Located in a restored 1930s neoclassical revival structure, this museum features over 50,000 items, from exhibits that showcase the town’s legacy as a transportation and manufacturing hub, to Native American and pioneer artifacts, and Civil War journals, among others. Notably, Cumberland is home to the Western Maryland Scenic Railroad, where one can enjoy scenic rides on steam or diesel locomotives through the Allegheny Mountains. An exciting weekend adventure, the three-hour-long rides are offered year-round and often include food and long layovers for shopping and dining.
For hikers and bikers, a weekend vacation to Cumberland is an opportunity to explore a part of the Great Allegheny Passage, which stretches 150 miles to Pittsburgh, Pennsylvania. From Cumberland, one can enjoy a 32-mile out-and-back adventure to Frostburg, a part of the trail that parallels the aforementioned railroad and features gorgeous mountain and forest scenery. Back in town, one can enjoy a pleasant weekend stay at the Hampton Inn Cumberland with cozy, well-equipped rooms, free hot breakfast, an indoor pool, and lots more.
Nothing beats a weekend getaway to these Maryland towns, especially in a state reputed to reflect the diverse geography of the entire country. From lovers of oceanfront vibes to those seeking mountain adventures, these towns in Maryland promise to leave no traveler unsatisfied. Meanwhile, those who love seafood will be spoiled for options in these towns, as the state is known for its rich fishing industry, with some of the towns, like Oakland and Boonsboro, offering fantastic fishing opportunities. Notably, Annapolis is known to be America’s sailing capital, making a weekend gateway to the town a chance for an unforgettable sailing experience. Dedicate a weekend to vacation in these towns in 2026 and enjoy more unforgettable experiences.
