Maryland's 8 Most Laid-Back Towns
Maryland is a geographically diverse state, from its mountains in the west to its beaches on the Eastern Shore. Within Maryland's borders, you will find charming, small, laid-back towns that are a delight to visit. These slower-paced small towns provide the ideal escape from the hectic, crowded life of the city. They may be small and relaxed, but these towns are anything but boring. Check out eight of the most laid-back towns in Maryland.
Berlin
You will feel the relaxed vibes as soon as you drive into Berlin in Worcester County. This small, historic town grew up along routes once used by the Assateague and Pocomoke peoples, whose paths crossed the land that became Berlin. The community developed in the 1790s around Burley Plantation, a 300-acre land grant dating back to 1677. It was officially named Berlin in 1868, becoming a welcoming stop for fishermen and travelers heading to the bustling resort town of Ocean City.
Almost 50 structures in town are on the National Register of Historic Places. As you walk through town, you can see the Atlantic Hotel, dating back to 1895, which was the setting for the 1999 movie "Runaway Bride." Burley Manor, built in the 1830s, is another historical landmark on Main Street. The laid-back feeling of Berlin continues as you go into Sterling Tavern on Main Street, serving pub food and alcoholic and non-alcoholic beverages in a relaxed atmosphere. Don't miss the Berlin Christmas Parade, held annually in December, featuring 80 floats, fire trucks, dancers, and Santa Claus.
Chesapeake City
Cecil County's tiny town of Chesapeake City sits on the Chesapeake & Delaware Canal, and is the only town in Maryland on a working commercial canal. It is a very relaxing experience to sit on a bench in Pell Gardens Park and watch vessels sail through the canal, which has been in use since 1829. If you are lucky, you might be able to catch a concert or other live performance in the park in the summertime.
Many historic buildings exist in this village, including the C&D Canal Museum, which was built circa 1837, and dives into the history of the canal connecting the Chesapeake and Delaware canals. The museum also features the Old Lock Pump House, a National Historic Landmark that once lifted vessels over the Delmarva Peninsula divide. If you would rather relax and watch ships pass by as you enjoy local seafood, dine at Schaefer's Canal House. The Chesapeake Inn Restaurant & Marina also offers spectacular water views, as well as live entertainment.
Chestertown
The town of Chestertown was founded in 1706 along the banks of the Chester River in Kent County. Today, it is a beautiful, historical town featuring Washington College, founded in 1782, the first college chartered in the sovereign United States. The quiet atmosphere of Chestertown makes it a small town you should not miss.
The Historical Society of Kent County in Chestertown explores the roots of the town and the area, and can give guests a self-guided map of a walking tour of downtown Chestertown. The downtown area is filled with art galleries, shops, bars, and restaurants. Winter events in this small town include the Winter Art Walk and a Dickens of a Christmas, both in December.
Easton
The town of Easton sits at the headwaters of the Tred Avon River in Talbot County. Easton has a historic feel, as it was once the colonial capital of the Eastern Shore. Its serene vibes make Easton the ideal place to relax and recharge.
Self-guided walking tours of Easton's historic district include exploring Bullitt House, built in 1801, which houses the Mid-Shore Community Foundation. The Avalon Theatre, known as one of the country's best Art Deco theaters, was founded in 1923 and still shows performances today. Don't miss the Amish Country Farmers Market in Easton for local baked goods, produce, meats, and delicious food.
Havre de Grace
Harford County's Havre de Grace, French for "port of grace," sits where the Susquehanna River meets the Chesapeake Bay. What better place to rest and enjoy the delightful scenery than over these waters? Havre de Grace has many historic landmarks to visit, as well as places to relax.
The Concord Point Lighthouse is 36 feet tall, and if you climb to its top, you will be rewarded with breathtaking views of the Susquehanna River. If you want to get a bit of exercise, check out the Lafayette Trail Tour, a self-guided tour consisting of three miles through the town. Grab a bite to eat and an alcoholic or non-alcoholic beverage at MacGregor's Restaurant along the Susquehanna River when you've finished exploring this quaint waterfront town.
Mount Airy
Situated in both Carroll and Frederick Counties, the town of Mount Airy is approximately 40 miles from both Baltimore and Washington, DC. It is the perfect place to escape the crowds of the big city, relax, and enjoy the fresh air. It is also home to Linganore Winecellars, the largest winery in the state, featuring more than 30 wines produced in an eco-friendly manner. Tours and tastings are available.
The Mount Airy Museum, located in the town's Mount Airy Station on Main Street, is a vast vault of information on local history and features free admission. A walk through the Mount Airy Historic District will take you to interesting landmarks, such as the Pine Grove Chapel and Cemetery, dating back to 1846. The Mount Airy Inn serves local Maryland seafood and libations when you are nearing the end of your visit in town.
North East
At the head of the North East River, the town of North East is popular with boaters, fishermen, and those who enjoy the water. It is also a quiet town in which to get away from it all for a while. The town is approximately an hour's drive from both Baltimore and Philadelphia, Pennsylvania, offering visitors a pleasant respite from the city's crowds.
The first permanent settlement in Cecil County, North East was settled by the English before the 1700s. The Upper Bay Museum features a collection of historical hunting and fishing artifacts from the town. North East Community Park along the North East River is a great place to relax, unwind, and visit with friends. Hungry visitors flock to Woody's Crab House for local seafood, or Chesapeake Bay Coffee Co. if they crave coffee and homemade baked goods.
Oakland
The county seat of Garrett County and the westernmost town in the state, Oakland is a beautiful, historic village near Allegheny Ridge of the Appalachian Mountains. Its charming downtown area is filled with historic buildings in which to relax and wander. Oakland, near both the West Virginia and Pennsylvania borders, is a little over an hour's drive from the college town of Morgantown, West Virginia.
Broadford Lake Park in Oakland features a lake with a beach and picnic area. For those looking for a more active park experience, check out Swallow Falls State Park, which contains the 53-foot-high Muddy Creek Falls and many walking trails. Visitors should not miss stopping in Englander's Antiques Grill and Soda Fountain, where they can browse through antique collections, then grab a snack or ice cream at the counter.
Slow Down and Visit These Small Towns
When you are searching for a quieter, serene spot to visit in Maryland, consider these eight small, laid-back towns. Whether you are searching for serenity in a coastal town like Havre de Grace or North East, or prefer the atmosphere of a mountain town such as Oakland, these towns showcase the best that Maryland has to offer: warmth, a welcoming atmosphere, and a quiet, relaxed vibe. Although they are laid-back, these towns are filled with plenty of fun activities to enjoy.
