6 Charming Small Towns Across Maryland

Maryland has some well known cities such as Baltimore and Ocean City. But, it’s also full of charming small towns, especially in the more rural areas. Here are a few sweet small towns we have visited. Geographically our list starts in the Western edge of Maryland and heads East, then south along the bay.

Oakland

The little town of Oakland is nestled in the Allegheny Mountains on the western edge of Maryland. It is near the state’s border with West Virginia. It has a charming, historic downtown with a peaceful, quiet atmosphere. Known as the snowiest city in Maryland due to its elevation, be prepared for chilly temperatures outside of the summer months.

The town features several interesting small museums. The B&O Museum has an old steam train outside; the Transportation Museum features all sorts of vehicles; and the Garrett County Historical Museum contains 9 rooms of exhibits related to the local history. We also had some delightful barbecue at Schweitzer’s BBQ in Oakland – some of the best we’ve had.

Another bonus is that it’s only a 10 minute ride to beautiful Swallow Falls State Park. Here a short hike gives you fabulous views of 7 waterfalls. It’s also very close to Deep Creek Lake State Park. The park sits along a beautiful, large reservoir offering plenty of opportunities for outdoor recreation. Find out more about Maryland’s state parks at this post.

Grantsville

Moving a little further east along the panhandle, Grantsville is closer to the Pennsylvania border. The town was founded in 1796 and incorporated in 1864. Here you will find Casselman River Bridge State Park, featuring one of the oldest bridges in the country, and the Spruce Forest Artisan Village. The village hosts a variety of artists making and selling their wares, including pottery, blacksmithing, and many other forms of art. Unique boutiques located in historic buildings offer a unique shopping experience. The Yoder History House offers living history displays and activities.

It is best to visit in the warmer months for most businesses to be open, but the atmosphere remains tranquil throughout the year. The Cornucopia Cafe has a unique and cozy ambiance if you’re looking for a fine dining experience. Other popular choices are the Casselman Inn and Restaurant or Penn Alps.

Cumberland

Moving east along the Panhandle brings you to historic Cumberland. This charming district is part of a larger town which was once a vital transportation and industry hub. Its revitalized downtown features many restaurants, cafes and shops that are easily walkable, such as the Baltimore Street Grill

The town is also known for the Western Maryland Railway and the vintage steam train rides that it offers. You can take a three hour excursion and see the stunning scenery of Western Maryland’s mountains from the comfort of your train car. Stop for a picnic meal or use the dining car if you get hungry.

There are many nearby opportunities for outdoor recreation, including Rocky Gap State Park, and long trails such as the C&O Canal Towpath and the Great Allegheny Passage.

Sykesville

Moving toward the center of the state before reaching Baltimore, you will find Sykesville in Carroll county. This charming small town hosts a picturesque main street, some beautiful homes, a gorgeous old church, and various unique boutiques and cafes.

Formed in the 1830’s around Howard Cotton Factory, the town retains several historic buildings. One is a historic “colored” school house that you can visit, a historic train station, and a visitor’s center inside a train car along with the post office. Browse A Likely Story bookstore and get a bite to eat at the French Twist Cafe. Check out the Sykesville and Patapsco Railway Museum or attend a concert at Cooper Park.

Havre De Grace

Keep on heading east and you will come to Havre De Grace, a sweet little townlocated where the Susquehanna River meets the Chesapeake Bay. The town was incorporated in 1785 and named for its resemblance to Le Havre, France, by the Marquis de Lafayette.

Known as the “Decoy Capital of the world,” you can visit the Decoy museum where you’ll find local carvings traditional to the area. Or, stroll along the “Promenade,” which is a little winding boardwalk along the Bay that ends up in front of the historic Concord lighthouse. Play at the playground on the hill above the marina which sports its own miniature Concord Lighthouse for children to enjoy.

The town has a variety of options for seafood and other dining, There are a number of charming waterfront restaurants nearby, such as McGregor’s Restaurant and Tidewater Grill. Visit nearby Susquehanna State Park for outdoor recreation.

Easton

If you head south through eastern Maryland, you will find the cute little town of Easton not far from the Chesapeake Bay. The town hosts an attractive blend of Colonial and Victorian architecture and numerous art galleries such as the Academy Art Museum. Founded in 1710, the historic downtown features the Third Haven Meeting House, built in 1682, and a farmer’s market running since 1752. Maritime activities are popular here, and the town offers easy access to other charming small towns such as St. Michael’s and Oxford.

For the little ones, Idlewild Park has a wonderful series of playgrounds. From there, it is a short walk to the town to enjoy some ice cream from Storm and Daughter’s or a bite at Doc’s Downtown Grill. If you’d like to enjoy some views of the water, head over to one of the local marinas or visit Easton Point Park.

These are just a handful of the lovely small towns you can find in Maryland, and we hope you enjoy finding many more as you explore the state. Find more information about family fun throughout all of Maryland’s regions at this post.