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Berlin, Maryland. By David - CC BY 2.0, Wikimedia Commons.

The 10 Friendliest Little Towns In Maryland

Traveling to new places can be intimidating, even scary. Not only visiting places you have never been to but also interacting with locals. Some residents don’t always like sharing their town with tourists, and that can cause hesitation for a lot of people. But sometimes you find yourself in a storybook town with people who love to see you there. These towns fit into that category. If you’re planning on a visit to Maryland, make sure to check out these 10 friendly small towns.

Berlin

Berlin, Maryland.
Berlin, Maryland. Editorial credit: Alexanderstock23 / Shutterstock.com

Start your Berlin trip at the Assateague Island National Seashore. The coastline offers its visitors different types of entertainment, whether on land or in the water. Go fishing or crabbing, take a dip in the ocean, hike or bike, or ride a horse down the beach. Make sure to only ride the horses offered at the stables, as you’ll probably encounter wild horses on the beach while traversing the seashore. For a more social experience, take a stroll down Main Street. Only eight miles from Assateague Island National Seashore, Main Street not only offers multiple restaurants and shops to meander through but is also part of the Art & Entertainment District. There are over 60 shops and more than 15 restaurants. Main Street is also one of the streets that participate in the town’s Farmer’s Market. Running every Sunday from May to October, the Market also stretches over Pitt Street and Commerce Street. More than 50 vendors participate and sell products ranging from Rum to candles to homemade pies.

Berlin, Maryland. Local businesses in Berlin, Maryland.
Berlin, Maryland. Local businesses in Berlin, Maryland. Image credit: Philip N Young via Flickr.com.

Saint Michaels

Historic house in Saint Michaels, Maryland.
Historic house in Saint Michaels, Maryland.

This quaint town is located on the Miles River. The river flows amongst tree-lined streets and ends in Chesapeake Bay. And that bay plays a large part in Saint Michael’s culture and history. Make the Chesapeake Bay Maritime Museum your first stop once you’ve arrived and experience more than a standard museum. The CBMM offers several exhibits and programs that provide a hands-on learning experience. Not only is this space a museum but also an active harbor, so come by boat for an enriching experience. Continue your learning experience by going to the Classic Motor Museum. The exhibit includes antique motorcycles, classic cars, and fuel-related paraphernalia, like a Texaco gas pump from the 1950s. If you come in the summer, enjoy the Summer Concerts in the Park. Every Thursday from May until August, a different musician plays a free live show.

St. Michaels Harbor in historic Saint Michaels, Maryland.
St. Michaels Harbor in historic Saint Michaels, Maryland.

Chesapeake City

A scenic view of Chesapeake City, Maryland.
A scenic view of Chesapeake City, Maryland.

Running along one of the busiest canals in the Â鶹AV is the tiny town of Chesapeake City. It is also the only town in the state that sits on a functioning commercial canal. Due to its deep history, the town has been named to the National Register of Historic Places. Make sure to immerse yourself fully by visiting the Chesapeake City Historic District. The district features restored homes, restaurants, antique stores, and an art gallery. Continue learning about the history at the Chesapeake City Museum. The museum pays homage to residents who excelled at their talents. MLB baseball player John Mabry, whose childhood was spent in Chesapeake Bay, has baseball cards on display. There are other town memorabilia, including newspapers from the 1940s, a washing machine from 1916, and more. If you want to get involved in present-day Chesapeake City, make sure to visit during their Spring Fling Charity Gala. There’s food, drinks, auctions and raffles, and a band to get everyone up and dancing. Mingle with the locals for a good cause!

View of Chesapeake City, Maryland.
View of Chesapeake City, Maryland.

Rock Hall

Sitting by the waterfront in Rock Hall, Maryland.
Sitting by the waterfront in Rock Hall, Maryland.

Rock Hall is located in Chesapeake Bay, so upon visiting, take advantage of all that the water has to offer. Experience the small beach at Ferry Park and take a swim while enjoying the sights of the bay. This park also offers immaculate sunset views over the bay. Continue taking in the views of the bay at the Haven Harbour South. The harbor is on a protected cove, so after docking, you can swim, bike, and relax at the beachside. The marina also serves as a venue for the town’s festivals, including Independence Day fireworks and poker nights. Take advantage of these festivals while in Rock Hall, as well as others located at Mainstay. Spending a night listening to traditional Bluegrass music on Main Street is magical. Rock Hill hosts multiple community events that involve music and aquatics. So, if you want the full experience of this small town, make sure to stop at one of their music events on the water.

Leonardtown

Downtown Leonardtown, Maryland.
Downtown Leonardtown, Maryland. Image credit Elvert Barnes via Flickr.com

One of Leonardtown’s most notable historical sights is the Moll Dyer Rock. Believed to have been a witch who plagued the town with influenza in 1697/1698, Moll Dyer allegedly froze to death on the rock now named after her. Her right hand left an imprint on the rock that the townspeople saw as a curse, still rumored to be true to this day. If you visit the rock, make sure to look but not touch it, as touching it is what is rumored to cause misfortune to those who do. Explore more of this town’s bizarre history with a visit to a jail cell. The Old Jail Museum, built in 1876 and operational until 1945, is located in the charming downtown area and is open for tours. The original rooms and cells remain to this day. If you’re looking for a more lighthearted experience, grab a blanket and some popcorn and head to Leonardtown Movie Nights. Socialize with your neighbors before watching the selected movie of the night.

The entrance to an antique and souvenir shop in Leonardtown, Maryland.
The entrance to an antique and souvenir shop in Leonardtown, Maryland.

Ocean City

Ocean City, Maryland Boardwalk.
Ocean City, Maryland Boardwalk.

Who doesn’t love hitting up a good boardwalk when in an ocean area? When you visit Ocean City, immerse yourself in the most traditional oceanside activity, touring the boardwalk. The Travel Channel hails it as one of the most exciting boardwalks in the US, so don’t miss this one! Mostly known for its food, the 3-mile stretch also offers activities, shops, and rides. Ride the Ferris Wheel to get the best views and eat saltwater taffy to get a taste of the ocean. Step away from the hustle and bustle of the boardwalk for a bit and learn more about Ocean City at the Ocean City Lifesaving Museum. Located at the end of the boardwalk, the museum pays tribute to and teaches patrons about the US Life Saving Services. The museum also provides stunning views of Assateague Island. Ocean City is also home to multiple music festivals throughout the year, including their popular Sunfest and Dreamfest. Most of the festivals take place on or near the boardwalk.

Boonsboro

 East Main Street, Boonsboro, Maryland.
East Main Street, Boonsboro, Maryland. Image credit Acroterion, CC BY-SA 3.0, Wikimedia Commons

Enjoy an afternoon outside at Devil’s Backbone Park. This park is the second oldest park in Washington County and allows visitors to fish, canoe, grill, and hike. Nestled along Antietam Creek, a footbridge crosses over the creek to take you to the “island” of the park. This section of the park offers a nature trail that will take you to the summit of the ridge. Another leisurely spot to visit in Boonsboro is Washington Monument State Park. The park has a rich history, including the Washington Monument, which was the first complete monument built in honor of George Washington. The monument itself was constructed by the town’s citizens. A town that erects a monument together makes you feel a strong send-over closeness, and you can join in that feeling at one of the town’s annual fests. For the past five years, Boonsboro has hosted the Food Truck Festival in Shafer Park. Enjoy food, music, drinks, and friendly competition.

East Main Street, Boonsboro, Maryland.
East Main Street, Boonsboro, Maryland. Image credit Acroterion, CC BY-SA 3.0, Wikimedia Commons

Thurmont

Loys Station Covered Bridge in Thurmont, Maryland.
Loys Station Covered Bridge in Thurmont, Maryland.

Thurmont is home to beautiful Catoctin Mountain Park, tucked within the Blue Ridge Mountains. The park offers 25 miles of hiking trails for visitors to take in the sights of Chimney Rock, Wolf Rock, Cunningham Falls, and more. Spend the day and enjoy all the nature this scenic park has to offer. Another park this charming town is home to is Cunningham Falls State Park. It is so popular that it is known to fill to capacity on Saturday and Sunday. Make sure to arrive early to get the most out of your visit. This park is also located within the Catoctin Mountains and has amenities for hiking, swimming, boating, fishing, hunting, and camping. With all these activities, it’s no surprise that this park has been filled up so quickly. When visiting Thurmont, if you’re lucky enough to come during restaurant week, you can dine at the establishments residents have been eating at for years. Feel like a regular at one of the many locally owned restaurants participating.

Downtown Thurmont, Maryland.
Downtown Thurmont, Maryland. Image credit Andrew Bain, CC BY-SA 3.0, Wikimedia Commons

Oxford

 Aerial view of Oxford, Maryland on the Chesapeake Bay with clouds, water and shoreline.
Aerial view of Oxford, Maryland, on the Chesapeake Bay with clouds, water, and shoreline.

Oxford, located along the Tred Avon River, showcases its nautical roots at the Water’s Edge Museum. The museum also presents accolades from the Founding Black Families of America. The museum is home to artifacts of black sailmakers, crab pickers, watermen, the military, and more. Visit the museum to learn how life was for black professionals and how they paved the way for the future. Near the museum, catch the Oxford-Bellevue Ferry and take what is considered one of the most scenic tours of Oxford. The ferry takes you across the Tred Avon River and allows you to visit other neighborly towns in the area. This service is also the oldest privately owned ferry service in the US, dating back to 1683. The Oxford community looks to embrace many talents of their residents, and the Oxford Community Center is one place for those talents to come together. Every Monday, they host a jam session, which is open to anyone who wants to come and play their instruments.

South Morris Street in the town of Oxford, Maryland.
South Morris Street in the town of Oxford, Maryland. Editorial credit: JE Dean / Shutterstock.com

Oakland

The Baltimore and Ohio Queen Anne Style Railroad Station building. Oakland, Maryland.
The Baltimore and Ohio Queen Anne Style Railroad Station building. Oakland, Maryland. Editorial credit: Kim Howell / Shutterstock.com

If you make it to Oakland during your Maryland trip, do not skip a visit to Swallow Falls State Park. Take in the awe-inspiring views of Muddy Creek Falls. The beautiful 53-foot waterfall is not the only attraction, though. Hike along the rivers and through the gorges on your way to the falls. After the state park visit, learn about the town’s transportation history at the Oakland B & O Museum. The museum tells the story of the two men who constructed multiple buildings along the tracks from Baltimore, MD, to Parkersburg, WV. B & O and the Pennsylvania Railroad were pitted against each other to be the major railroad line to the west. If you visit Oakland in the winter, be sure to participate in its annual Winter Fest and Wine Walk. The Winter Fest provides live music, theater performances, markets, and hand-carved ice sculptures. Join the crowd at the festival before heading out on the Wine Walk, but only if you’re over 21!

Swallow Falls State Park at Canyon Trail located in Oakland, Maryland.
Swallow Falls State Park at Canyon Trail located in Oakland, Maryland.

If you’re looking for a welcoming visit to Maryland, plan a stay at one or more of these 10 friendly towns and explore all they have to offer. Visit beaches, take a hike, explore history, and participate in local festivals and community activities. See what life is like somewhere other than what you call home and spend time with the town locals to really get the feel of life in the area.

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