7 Best Maryland Towns For A Weekend Trip
Maryland offers an impressive variety of weekend destinations, from historic waterfront cities to charming mountain and beach towns. Annapolis and Ellicott City invite travelers to step into centuries of history alongside vibrant dining scenes, while places like Chesapeake City and Boonsboro provide slower-paced escapes filled with heritage and character. Whether wandering brick-lined streets, enjoying scenic trails, or settling into a cozy inn, these towns showcase the many ways a Maryland weekend trip can feel refreshing, memorable, and full of discovery.
Annapolis
The city of Annapolis, which also serves as the state's capital, is an attractive spot to visit and explore for a weekend, thanks to its distinct 18th- and 19th-century architecture, vibrant and iconic waterfront, and renowned seafood scene. For the discerning history buff, the city served as the temporary capital of the United States from 1783 to 1784, and it was here that George Washington resigned his commission before the Continental Congress. A visit to Susan Campbell Park, on the city's waterfront, is a must for jaw-dropping views of the Chesapeake Bay and the boats traveling in and out of the harbor. The park is also within walking distance of numerous attractions, shops, and restaurants to explore.
The Middleton Tavern, which was established in 1750, is a quick walk from the park for fresh seafood and live music in a historic venue that has hosted such notable figures as Thomas Jefferson, Benjamin Franklin, and George Washington himself. Not too far from the harbor is 134 Prince, a luxury boutique hotel offering its guests elegant and luxurious suites that reflect the city's heritage. It is set in a Colonial-style building surrounded by wonderful shops and restaurants, and makes for a comfortable and convenient home base in Annapolis.
Ellicott City
Unlike Annapolis, where the action is centered around the harbor, the excitement in Ellicott City begins on Main Street, where visitors can explore the B&O Ellicott City Station Museum and learn about the oldest surviving railroad station in the country, built in 1831. The museum offers guided tours by appointment, but general admission is free with highlights that include model trains, historic artifacts, and photographs.
Beyond the museums, numerous buildings from the 18th and 19th centuries are well-preserved and home to many local shops, businesses, and restaurants downtown. Matcha Time Gift Shop sells local gifts and souvenirs, and Candles by Candy Candle Bar is a unique spot where people can purchase special candles and even make their own. The Ellicott Distilling Company serves up tasty bites and signature cocktails made from spirits distilled in-house with numerous flavor combinations. They also offer distilling classes for a truly unique and memorable experience. On the northwestern end of town is the Turf Valley Resort, surrounded by lush golf courses, spas, and everything you could possibly need to enjoy a weekend getaway in Ellicott City.
Chesapeake City
Near the Delaware State Line, Chesapeake City has a very walkable and historic downtown with cozy restaurants, shops, and hotels, like the Inn at the Canal. The four-star hotel, built in 1870, offers lovely and comfortable rooms, as well as a bar where guests can enjoy drinks in the evening. Right on Back Creek is the Bayard House Restaurant, situated in an 18th-century building that serves its guests elegant meals and drinks with views of the waterfront and an inviting interior.
The C&D Canal Museum invites visitors to learn more about the history of the Chesapeake and Delaware Canal, which connects the Chesapeake Bay and the Delaware River, and the canal's importance today. For an up-close look at the canal, hop on the Ben Cardin segment of the larger C&D Canal Trail and bike, run, or walk along the waterfront to your heart's content.
Boonsboro
The historic town of Boonsboro served a role in the US Civil War and has wonderful museums and shops to explore, offering a quiet escape. The historic Inn BoonsBoro is owned by New York Times bestselling author Nora Roberts and welcomes guests in the heart of downtown. The Pathfinder Farm Distillery Tasting Room and Cocktail Bar is within walking distance of the hotel and serves handcrafted moonshines, whiskeys, and bourbons in a historic log home.
There are three museums to visit in the community. The National Road Museum explores the history of the first federally constructed roadway that runs through town, which is known as US Route 40 today. The Boonsboro Trolley Museum, which is located in the community's original station, has exhibits and artifacts showing the history of local and regional transportation systems, while the Boonsboro Museum of History showcases historic artifacts and exhibits related to the Civil War and the Battle of Boonsboro, which took place here in 1863.
Frederick
East of Boonsboro is the town of Frederick, home to plenty of unique and wonderful shops, a fun and attractive arts and entertainment district, and more history related to the Civil War. In the middle of it all is Carroll Creek Park, which is a 1.5-mile greenbelt and a hub for festivals and community events, like the Frederick Festival of the Arts held each summer in June. Within walking distance of the park is the National Museum of Civil War Medicine, where visitors can learn about the medical procedures performed on wounded soldiers, the medicines used, and medical advancements from that period.
Further down Patrick Street is the Maryland Ensemble Theatre, which hosts engaging plays, musicals, and concerts, along with local events for everyone to enjoy. On the southern end of town is the Hollerstown Hill Bed and Breakfast, a charming spot perfect for a weekend getaway in a Victorian home built in 1901. The rooms are well-appointed and decorated in period decor, the grounds include a lovely garden, and breakfast is served daily.
Oakland
Oakland is full of historic charm and boasts access to numerous outdoor activities due to its location near the Allegheny Mountains of the Appalachian Mountain range. The Mt. Nebo Wildlife Management Area is a great spot to explore lush forests and wetlands, not to mention birdwatching and wildlife spotting. Back in town, the Oakland Golf Course is home to an 18-hole championship course with immaculate views of the Appalachian Mountains. Golfers can even enjoy a wonderful lunch or dinner at the Caddyshack Bar and Grill after their round.
The Oakland B&O Railroad Museum teaches visitors and residents about the railroad's pivotal role in the formation of the town, has fun exhibits indoors and outdoors, and is a wonderful place for train enthusiasts. Not too far from the museum is Our Town Theatre, which hosts local productions in an intimate and casual venue. Right on 3rd Street, which is also US Route 219, the Oak Mar Motel has air-conditioned rooms, free WiFi, and the 3rd Street Diner right in the lobby for a quick and easy spot to rest while you explore the town and surrounding natural wonders.
Ocean City
The iconic resort town of Ocean City sits right on the Atlantic, and the Ocean City Boardwalk and Ocean City Beach are the places to be in summer. In the heart of the action, Park Place Hotel offers its guests rooms and suites with stunning views of the beach and the ocean, steps from the glorious 10-mile stretch of sand, ideal for volleyball, soaking up the sun, surfing, and boating.
Baltimore Avenue is just as walkable as the boardwalk. Here, visitors can find the Museum of Ocean City, which is housed in an old bank building and has old photographs and memorabilia from the town's past on display. Just down the street is Soriano's Restaurant and Coffee Shop, where patrons can enjoy a freshly brewed cup of coffee, homemade omelets, buttermilk pancakes, and a freshly made lunch with a side of people-watching on the central patio along Baltimore Ave.
A Memorable Weekend Awaits in Maryland
From the harbor views of Annapolis to the rail history of Oakland, these Maryland towns create ideal settings for a short getaway. Frederick and Boonsboro appeal to history lovers, while Chesapeake City and Ocean City deliver waterfront charm in distinct styles. Each destination offers inviting accommodations, walkable districts, and engaging attractions that fit neatly into a weekend. Together, these towns highlight Maryland’s rich mix of culture, scenery, and experiences worth savoring.
