10 Must-Visit Small Towns in Maryland

Berlin is a small town located just 10 miles from Ocean City, tucked into the countryside in eastern Maryland. This charming town offers everything from antique shops filled with treasures to delicious restaurants in historic buildings.

If you’re a fan of art, make sure to stop by on the second Friday of every month for an art stroll where you can listen to live music, check out the art on display and shop for some unique souvenirs. Berlin is also a town with year-round festivals you can enjoy a ton of different outdoor activities from concerts in the park to the popular peach festival in autumn.

Bel Air is a small town in northern Maryland, just 45 minutes north of Baltimore. People come from all over to spend an afternoon downtown shopping at one of their many local boutiques, dining at their delicious restaurants and grabbing a beer at one of their breweries.

Like many other small towns along the east coast, Bel Air was a stop along the underground railroad. The best way to explore its history is by booking a tour at the Hays-Heighe house on Harford Community College’s campus just a few miles from downtown Bel Air.

Havre de Grace is a charming little town on the coast along the Susquehanna River in northern Maryland. Located at the top of the Chesapeake Bay, one of the best places to visit in this small town is the promenade, which ends at the fully restored Concord Point Lighthouse. This lighthouse is not only a stunning place to take photos but also has an impressive museum and gift shop filled with some great local souvenirs.

For seafood lovers, Havre de Grace has some of the best restaurants around. From steamed crabs to oysters on the half shell, their waterfront restaurants and cafés downtown are a great way to enjoy the flavors of the Chesapeake.

St. Michaels is a picturesque town on the eastern shore of Maryland that was once a busy seaport and truly embraces small-town living. Today, people come from all over to enjoy a relaxing day by the water perusing unique shops along Talbot Street, sipping wine at the local winery and sailing on a harbor cruise through the bay.

Because St. Michaels is situated on the Chesapeake and was an important stop for sailors, its nautical history is quite impressive. Make sure to stop by the Chesapeake Bay Maritime Museum when you visit to experience its 18-acre waterfront, outdoor and indoor exhibitions, marina and more.

Mount Airy is a rural town in central Maryland, just 45 minutes away from both Baltimore and Washington DC. Take a stroll along the main street and enjoy some retail therapy at one of their many specialty shops and art galleries or grab a bite to eat at one of the local bistros and cafés.

If you’re looking for an awesome way to spend your afternoon, stop by one of the local wineries within a few minutes’ drive of downtown. Some of the most popular include Elk Run Vineyards, and Linganore Winecellars, which both offer wine testings and tours as well as some great live music.

Saint Mary’s City is a historic town in southern Maryland over 2 hours south of Baltimore. This small town was the first capital of the state of Maryland and a visit to Saint Mary’s City makes you feel like you stepped back into the 17^th century.

Located on the western shore of the Chesapeake Bay, the views from downtown are serene. One of the best ways to experience authentic colonial life is by stepping aboard the tall-ship Dove and taking one of their superb informative tours. This ship is a reconstruction of the original ship that docked here when the colony was first formed.

Easton is home to a stunning downtown area filled with upscale boutiques, incredible restaurants and eclectic art galleries. Located halfway between Baltimore and Ocean City, this small town has kept its historic charm alive through beautifully restored buildings.

Easton has a bustling arts culture with outdoor summer performances, a busy concert schedule at The Avalon Theater, and a prestigious air painting competition at the annual Plein Air Art Festival. For those who love to spend time outdoors, Easton is along the Chesapeake Views bike loop, a 38.2-mile scenic trail offering some incredible water views. If you’re more into sailing, canoeing or kayaking, just hop in the automobile and you’ll be at the bay in just a few minutes.

New Market is a small town in central Maryland, just 50 minutes west of Baltimore. Known as the Antique Capital of Maryland, people come from all over the state to browse the shelves of their unique shops. The best place to start your day in New Market is on main street, where you’ll find the majority of their antique stores and a few charming restaurants and cafés.

If you’re looking for something the whole family can enjoy, make sure to stop by The Original Playhouse, a children’s museum on Main Street, or head to Adventure Park USA, a nearby theme park with laser tag, bumper automobiles, small roller coasters and arcade games.

Pocomoke City is a historic town in southern Maryland, just a few miles north of the Virginia border. Located along the Pocomoke River, the small downtown is filled with quaint cafés and shops. One of the most popular attractions in Pocomoke City is the Delmarva Discovery Center. This museum features exhibits on the history of the colonies as well as the natural world of the Delmarva peninsula.

If you are visiting on a beautiful day, make sure to spend time on their nature trail. This 1.5-mile trail starts on the city dock at Cypress Park and takes you along the beautiful waterfront and through the woods.

Monkton is a beautiful small town located 40 minutes north of Baltimore. Gunpowder Falls State Park surrounds this small town and the Monkton Station is a popular drop-off point for tubing down the river. While there are tons of trails throughout the park, one of the most unique is the Northern Central Railroad (NCR) Trail. The NCR trail goes through Monkton Station and runs along an abandoned railroad up to the Pennsylvania border.

No visit to Monkton is complete without stopping by Ladew Topiary Gardens. Here you’ll find 22-acres of award-winning gardens, a serene nature walk, the beautiful historic manor house and a quirky gift shop.