7 Perfect Destinations for a Long Weekend in Maryland

Maryland, also known as "the Free State" or "the Old Line State," is mostly recognized as the home of Baltimore, but it also offers much more, with sprawling communities, historic towns, and coastal cities throughout the state. Each community has its own historical importance, unique charm, plenty of activities and local amenities to enjoy, great places to relax, and is a perfect spot not only for a long weekend visit but also as a potential new home for those looking to settle down.

These communities offer access to explore the Chesapeake Bay, the Appalachian Mountains, and numerous other state parks, each filled with relaxing natural scenery to discover during a long weekend. Each of these communities is a perfect place to visit, regardless of the season, but summer is the best time to visit some of them due to their proximity to beaches, bays, and oceans.

Annapolis

Annapolis is the state capital, with a population of 40,812, and is filled with an endless number of exciting amenities to keep people occupied for a long weekend. The city is known as "America's Sailing Capital" due to its location on the Severn River, the U.S. Naval Academy's presence in the city, and its historic 18th-century architecture.

One of the best areas in the city to visit is the waterfront, which is breathtaking, and there are thriving local businesses, restaurants, and bars that keep people coming for more. A notable restaurant to visit is the Middleton Tavern, a tavern that has been serving excellent home-cooked meals since 1750 and has hosted George Washington, Benjamin Franklin, and Thomas Jefferson during their travels. The Tavern went through numerous transformations over the decades, but has remained a staple of Annapolis.

Another historical building to visit in the city is the Maryland State House, which is one of the oldest state capitol buildings still in use today by the state government. The building hosted the Continental Congress from November 26, 1783, to August 13, 1784, and witnessed the Treaty of Paris ratified. Visitors must show a photo ID before touring the historic landmark.

The rest of the city is filled with old cobblestone streets, colonial architecture, and incredible local businesses and art galleries to explore. On Prince Street is the William Paca House & Garden, a Georgian mansion built in the 1760s by William Paca, who was a founding father and the third governor of the state. The property was once a hotel from 1901 until 1964, when there were plans to replace the colonial-style building with mixed-use development. However, Historic Annapolis Inc. acquired the property, restored the mansion, and has been a museum since 1965.

Cumberland

In the western part of the state is the city of Cumberland, located on the Potomac River and the West Virginia State Line. The city is nicknamed "the Gateway to the West" due to its role as a transportation hub and being the starting point for the country's first national road, which is known as U.S. Route 40 today.

Cumberland may not be a beach town, but it has its unique attractions, like the Western Maryland Scenic Railroad, which gives its guests an unforgettable railroad ride through the region and the Allegheny Mountains, especially when the sun sets, making the ride more scenic. The railway uses steam locomotives, and the #1309 locomotive (nicknamed the Maryland Thunder) is the most iconic train of them, as it was the last steam locomotive built for domestic service, and was purchased by the Western Maryland Scenic Railroad in 2014.

Similar to Annapolis, Cumberland also has a magnificent downtown with buildings from the 19th and 20th centuries still in place. A great place to learn more about the city's past is the Gordon-Roberts House, a Victorian-style home built in 1867 by Josiah Gordon, a prominent attorney and judge, who lived in town, and also housed W. Milnor Roberts, an engineer who built railroads. The house, which is now a museum, takes visitors back to a time when computers, phones, and tablets weren't a thing and what life was like in the 19th century.

Outside of the city, nature surrounds the area, and visitors can explore the Dan's Mountain Wildlife Management Area, a nature reserve that holds the largest contiguous state-owned forest. The reserve has mountains ranging from 900 to 2,800 feet, giving hikers and visitors breathtaking views of the area and the Potomac River flowing through. The longest trail to adventure in Dans Mountain is the Lonacona Loop Trail, a 4.4-mile-long trail perfect for hiking and mountain biking.

Havre de Grace

Just 41.6 miles northeast of Baltimore is Havre de Grace, a city in Harford County with a population of roughly 15,000. Havre de Grace is known for its historic charm, its location on the Chesapeake Bay, and the community played a role in the War of 1812 when British forces raided the town at that time. A landmark to visit that overlooks the Chesapeake Bay is the Concord Point Lighthouse, a lighthouse constructed in 1827, and it is the second-oldest lighthouse in the state. The lighthouse is currently a museum welcoming guests from all over to explore the historic facility and learn more about history.

Not too far from the lighthouse are two more museums to visit, the Havre de Grace Maritime Museum and the Havre de Grace Decoy Museum. The Maritime Museum preserves maritime heritage, fishing artifacts, commercial fishing, crabbing, and the environment around the Chesapeake Bay and Susquehanna River. The Decoy Museum, on the other hand, focuses its attention on the preservation of duck decoys, their manufacture, and the history of waterfowl hunting in the region.

Downtown Havre de Grace is a lovely spot filled with local restaurants, bars, and shops waiting to be explored during a long weekend. A great place to visit for a nice meal on the water is Tidewater Grille on Franklin Street. The restaurant gives patrons excellent views of the Susquehanna River and the Chesapeake Bay region, and offers a variety of wonderful seafood. Tidewater Grille also hosts events, live music, and brunch, making it a superb restaurant to visit for the long weekend away from the cities.

Salisbury

Further east from Havre de Grace in the Eastern Shore region of the state is the city of Salisbury, a community with a population of 33,050. Salisbury is known for its historical significance, natural attractions, and its role as a hub in the Eastern Shore region. A natural place to explore in town is the Salisbury Zoological Park, also known as the Salisbury Zoo, a zoo housing over 100 different animals, including flamingos, river otters, Canadian lynx, bison, rescued birds of prey, a red wolf, and many more. Admission to the Zoo is free for all visitors, making it a fun place to visit with the family on a long weekend.

A historic building to visit in town is the Poplar Hill Mansion, an 18th-century manor house that became the home of Dr. John Huston during the 19th century. It has been preserved and showcased to visitors from far and wide. People can even have a wedding or book other events at the mansion. There is an urban legend that five or six ghosts supposedly haunt the mansion, but they are said to emit positive energy, as their stories add to the charm of the mansion itself.

Salisbury's downtown is very quaint, charming, and very welcoming to all who drive through it and those who visit the community. The Riverwalk Park Edible Garden in the heart of downtown is a must-visit and is Mayor Jake Day's vision of having more edible landscaping in the community. The garden has strawberries, blueberries, herbs, native plants, and other native plants that provide habitats for pollinators. It is open to the public to enjoy all year round, with exquisite views of the city all around.

St. Michaels

Just 57 to 64 miles west of Salisbury is the town of St. Michaels, a community with a population of 1,094. The town is known for its rich maritime history, its unique waterfront setting, and its vibrant culinary scene. Being a town on the waterfront, St. Michaels has plenty of hotels, museums, and restaurants on the Miles River, including the Chesapeake Bay Maritime Museum, a museum that explores and preserves the maritime history in the community, holds unique maritime artifacts, historic vessels, and hosts various events, from weddings, private events, and private charters.

A great hotel to visit for a long weekend in town is the St. Michaels Harbour Inn, Marina and Spa, which is also right on the waterfront of the Miles River. The hotel provides guests with a luxurious stay, a marina giving boat and yacht owners access to explore the Miles River, and has a restaurant called Harrison Harbor Lights, a tavern, outdoor decks, and a dining room offering patrons a panoramic view of the area.

A great restaurant to visit in town that also overlooks the Miles River is Foxy's Harbor Grille. The restaurant serves patrons home-cooked seafood, especially homemade crab-cakes, excellent burgers, drinks, and spirits served right on the harbor. Foxy's also hosts events from small to large with breathtaking views of the St. Michaels Harbor from the gazebo, lookout lounge, or main bar.

Berlin

Further east of St. Michaels and Salisbury is Berlin, a town with a population of around 4,485. Berlin is known for its small-town charm, historic architecture, and was a filming location for the movie "Runaway Bride" starring Julia Roberts and Richard Gere. Berlin's Main Street is filled with charming local restaurants and shops that'll keep people entertained and occupied during a long weekend away from major cities.

An interesting place to visit in town is the Mermaid Museum, located nine miles from the sea and dedicated to all things mermaids, including lore, paintings, sculptures, and history. The museum opened in 2021 and is located in the heart of a quaint downtown area. The museum even allows people to take a photo posing in a bathtub with a mermaid's tail.

Another museum to visit in town is the Calvin B. Taylor House Museum, which is a 19th-century mansion built for Isaac Covington and his family. It was saved from demolition in 1981 and serves as a town museum preserving the history of Berlin. The interior of the house was restored to how it was in the 1800s, and the second floor serves as a gallery showcasing the story of the town. Taylor House also hosts events, such as storytelling, music, movie showings, and much more.

An excellent place to stay in town is the historic Atlantic Hotel, a hotel that opened its doors in 1895 in the heart of the Historic and Entertainment District, and was restored to Victorian era décor, giving guests a luxurious stay during their long weekend in town. The movie "Runaway Bride" was filmed in town, and the hotel's most famous room is the Richard Gere room, which Gere himself used.

Ocean City

About nine to 10 miles east of Berlin is the iconic beach community of Ocean City. Ocean City itself is known for its fishing history and immaculate beaches, and it is nicknamed "White Marlin Capital of the World." The beach in the community is a major reason why people are attracted to the iconic beach city, as its 10-mile stretch is known for its family-friendly atmosphere, the boardwalk with endless amounts of restaurants and shops, and is regarded as one of the best beaches to visit in the country.

Another excellent place to visit in town is the Jolly Roger Amusement Park, an amusement park with five different parks wrapped in one: The Jolly Roger Mini Golf course, Jolly Roger at 30th Street, Jolly Roger at the Pier, and the Splash Mountain Water Park, which features 16 slides. Each of these parks has fun rides for all ages and will make a memorable experience for friends and families visiting the city during the summer.

A historic place to visit in town is the Ocean City Life Saving Station Museum, which is dedicated to preserving the history of the city through its programming and exhibits. The museum was once the Ocean City Life Saving Station, which the U.S. Coast Guard used to save vessels in distress and people in trouble in the ocean until 1964. The building was scheduled for demolition in 1977 until the citizens of the city stepped up, formed the Ocean City Museum Society, and saved the building from demolition, and moved it to the southern end of the boardwalk, where it overlooks the entire inlet. The museum has a preserved collection of photos and images of what the city looked like in the past for the present generation to observe and explore.

Each of these destinations serves as a reminder that smaller Maryland communities have their unique charm, historical sites, and exciting quirkiness, making them standouts for a visit. Whether it's prominent beach communities or towns nestled within the forests, each of these towns is warm and welcoming, relaxed in pace, and offers excellent choices for people ready to settle down. These communities are sure to leave a positive impact on anyone visiting or calling "the Free State" home.