St. Michaels Maryland aerial view panorama in Chesapeake bay. Image credit Andrea Izzotti via Shutterstock.

Most Underrated Towns in Maryland

Maryland is chock full of history and culture, as well as beauty and charm, which makes it worth the visit. The state sits amidst the dense forests of the US and along the coast of the Atlantic Ocean, meaning there is plenty to see and do.

While there are many beautiful cities to tour through–and maybe even retire to–in Maryland, there are a number of exciting and charming towns to explore. Here's a list of the most underrated towns you need to visit in Maryland.

St. Michaels

The harbor in St. Michaels, Maryland. Image credits: Jon Bilous via Shutterstock

Located on Maryland's Eastern shore, St. Michaels is home to a scenic harbor and the Chesapeake Bay Maritime Museum. The small town is the ideal location if you're curious about the state's maritime history, or if you want to indulge in activities such as sailing, kayaking, golfing, and bicycling. 

Nestled in the harbor, the town's seafood and waterfront restaurants are something you can't miss. And if you pay a visit during winter, be sure to check out the town's Christmas celebrations. You can explore the many boutiques and gift shops and relish in the jolly spirit of the Christmas village.

Bel Air

Bynum Run Creek in Bel Air, Maryland. Image credits: zachmaclellan4 via Shutterstock

Nestled in Hartford County, Maryland, Bel Air is known for its thriving arts community and armory. The armory park is also home to landscaped gardens, benches perfect for relaxation, and a stage area for performances. 

Stop off at Bel Air and pay a visit to one of the town's many concerts, art galleries, or memorable holiday cultural events. You can also enjoy a self-guided public art tour and visit 23 different sculptures and murals.

Chesapeake City

View of Chesapeake City from the Chesapeake City Bridge, Maryland. Image credit Jon Bilous via Shutterstock.

It's no surprise that Chesapeake City–actually a small town–is situated on Chesapeake Bay. The town is on the National Register of Historic Places as it bridges the bay and the Delaware River, operating as a commercial canal.

Most of the town's 19th-century architecture still stands, and visitors can also enjoy dining and nightlife, trails, water cruises, boutiques and shops, and more! And if you'd like to stay a little longer, check out one of the cozy bed and breakfasts

Oakland

Oakland Station in Western Maryland. Image credits: Jason Knauer via Wikimedia Commons

A visit to Oakland, Maryland, consists of walking trails, parks, shopping trips, and events and festivals. The beautiful outdoor locations are perfect for picnicking, adventuring, and time well spent.

The town also boasts a vibrant art scene where visitors can enjoy different sources of entertainment, ranging from galleries to musical events and plays. And if you've got an inkling to shop, check out Maryland's main street.

Finally, don't forget the Historic District, where you'll find beautifully restored Victorian buildings.

Vienna

Intersection of Market and Race Streets in Vienna, Maryland. Image credits: Acroterion via Wikimedia Commons

Located on the Nanticoke River, Vienna is one of the oldest colonial settlements in Maryland. It is known as a historic waterfront town as it boasts access to a 1768 Customs House, the Vienna Heritage Museum, as well as a waterfront park.

With an abundance of inns and bed and breakfasts to choose from, you can stop in for a weekend or take your time and enjoy the historical and cultural stories of the town.

Leonardtown

A pier juts into the mirror-like waters of Breton Bay, in Leonardtown, Maryland. Image credit TJ Brown via Shutterstock.

Leonardtown is home to picturesque landscapes and waterways, as well as historic buildings, specialty shops, galleries, and scrumptious restaurants. Visitors will also find a quaint town square that is charming and walkable, ideal for a relaxing visit.

If you do visit, don't forget to check out the town's art scene, including one-on-one art classes and entertaining shows. It's also the perfect spot to visit during the holidays, with a beautiful tree lighting ceremony, meetings with Santa, and more.

Visit These Towns and Be Mary(land)!

It's safe to say that Maryland is home to a plethora of unique small towns ideal for weekend adventures and exciting getaways. Whether you're interested in picturesque views, outdoor activities, delving into the history, or everything in between, add these small towns to your bucket list.

There's plenty to explore and see, and the only thing that will make your trip better is if you check out more than one!

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