The Best Towns To Visit In Maryland

CALIFORNIA, Md. — Even if you’ve lived in Maryland for a lifetime, there are always new hidden gems to discover in our historic state. Fans of small towns will love the distinct atmosphere in Leonardtown Square, while big city people may prefer the hustle and bustle of Bethesda. Our list will walk you through the best towns and communities to visit in Maryland, plus a few fun activities waiting for you at each location.

Click here for a look at the best museums in St. Mary’s County.

Annapolis

Whether you attend a ghost tour, cruise around the Chesapeake, or simply walk around a variety of adorable shops, Annapolis is a must-visit for every Marylander. Annapolis is a historic capital city, and walking its streets is a great way to enjoy a chilly evening in the winter. To find out more about the expansive list of activities in Annapolis, go to VisitAnnapolis.org.

Leonardtown

Leonardtown is one of the most interesting cities in Southern Maryland, especially if you like town squares. Leonardtown Square is packed full of things to do, along with an assortment of restaurants and shops. Take an art class at Crafts N Stitches or grab a warm drink at Social Coffeehouse. Leonardtown is a fun place to visit in St. Mary’s County, and it has ample activities to partake in year-round.

Historic St. Mary’s City

Historic St. Mary’s City is the original capital of Maryland, and there are a plethora of attractions to be found here if you love history. Reenactors will guide you through your adventures, and you can visit various buildings within the city to find out about how people lived hundreds of years ago. If you want to brush up on Maryland history or have a unique experience in the outdoors, then Historic St. Mary’s City is the destination for you.

Bethesda

Walking around Bethesda in Montgomery County feels like exploring a small version of a big city. Between the upscale restaurants and variety of events, there’s always something interesting to see in Bethesda, like the Round House Theatre. If you’re looking for shopping, then the Bethesda Row mall is a fantastic option due to its large number of different stores. Bethesda is the perfect place for a shopping spree, and there are endless options for dining when you get hungry, too.

Frederick

For Marylanders seeking a city farther to the north, Frederick is a great place to visit. Downtown Frederick is a treat for shoppers and sightseers due to its collection of stores, restaurants, galleries, and more. Carroll Creek Park is a beautiful spot for a stroll on a sunny day, while the National Museum of Civil War Medicine offers a fascinating look at the history of the United States. There’s a lot to do in Frederick, which is why it’s one of the best cities to visit in Maryland.

St. Michaels

St. Michaels is a peninsula town in Maryland, and boat rides, shops, and B&Bs await in this small community. The Chesapeake Bay Maritime Museum is a local gem, and the boating will leave you longing for life on the water. If you’re seeking a quiet afternoon or weekend in an adorable Maryland town, then St. Michaels is the ultimate option.

Cumberland

Cumberland is an enchanting town in Western Maryland. Take a beautiful ride on the Western Maryland Scenic Railroad, then head to downtown Cumberland for a delicious meal from a variety of restaurants. There are plenty of places to hike in and around the mountains of Cumberland, so this town is a hub for nature lovers.

Havre de Grace

Havre de Grace is a small town nestled in northeast Maryland. It offers scenic water views of the Susquehanna River and art decorating the streets, plus a few local attractions like the Havre de Grace Maritime Museum. If you enjoy strolling through small towns rich with history and unique shops, then Havre de Grace is calling your name.

Ellicott City

The 19th-century architecture of Ellicott City’s Main Street is a feast for the eyes, though the true point of interest is the Ellicott City Station Museum, where you’ll get a fun history lesson about the oldest passenger railroad station to survive until 2025 in the United States. Festivals and shops are also abundant in Ellicott City, as it’s one of the most popular towns in Maryland.

Ocean City

If you’re heading to the Eastern Shore, then drop by Ocean City for a day of excitement under the sun. Between the Jolly Roger Amusement Park and numerous ice cream shops, there’s ample fun to be had in Ocean City, especially in the summer. Beaches are a hub for relaxation for all ages, so Ocean City is the perfect town for your next vacation!

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