The Most Underrated Towns In Maryland

There's an argument to be made that Maryland is underrated, particularly when it comes to a few of its small towns. Oakland sits on the "other side" of Deep Creek Lake, a 20-minute drive that many vacationers never make. Havre de Grace is home to the 1827 Concord Point Lighthouse, the oldest accessible lighthouse in the state. Just 15 minutes from the Ocean City crowds, Berlin offers a Victorian Main Street so pretty it has served as a filming location for several Hollywood movies. On South Mountain above Boonsboro, Washington Monument State Park is the site of the first completed monument dedicated to George Washington. Together, these eight towns reveal a quieter side of Maryland, where historic streets and long-standing traditions warrant a visit.

Oakland

Because it is on the "other side" of Deep Creek Lake, many people have never visited the town of Oakland, Maryland, in Garrett County. It is just a 20-minute drive from the lake, and well worth it. Oakland has important things within walking distance, amid the beauty of the Allegheny Ridge of the Appalachian Mountains. Visit in October, and you can be part of the town's annual five-day Autumn Glory Festival, complete with parades, food, car shows, and breathtaking autumn colors.

The Suites at Silver Tree offers guests luxurious lodging with a restaurant, game room, and on-site fitness center. During your walk around Oakland, be sure to stop by Englander's Antiques Grill and Soda Fountain, an 80-year-old retail store with a 50s-style soda fountain and grill attached. If you want to sample local produce and home-baked goods, check out the Mountain Fresh Farmers Market, Garrett County's longest-running, producer-only market, held on Wednesdays and Saturdays from June through October.

Havre de Grace

Meaning "Harbor of Grace" in French, the Harford County town of Havre de Grace sits where the Susquehanna River meets the Chesapeake Bay. It is a beautiful, historic waterfront town, often characterized by its iconic Concord Point Lighthouse, built in 1827, the oldest lighthouse in the state that is publicly accessible. The Havre de Grace Promenade, a 0.75-mile-long boardwalk along the Susquehanna River, stretches from the town's Concord Point Park to Millard Tydings Memorial Park and offers awe-inspiring views of the river and the wildlife that inhabits it.

Just a short walk from the Promenade, Vandiver Inn Bed and Breakfast was built in 1886 and offers modern-day guests comfort and hospitality. One local shop that sweets lovers will want to visit is Bomboy's Candy. The shop's famous handcrafted chocolates, as well as homemade ice cream, keep customers coming back for more.

North East

Sitting along the North East River at the head of the Chesapeake Bay, the small waterfront town of North East, in Cecil County, offers opportunities for recreation both off and on the water, as well as shopping and dining in its compact downtown district. Turkey Point Lighthouse is a must-see. This 1833 lighthouse sits high on a 100-foot-tall bluff inside Elk Neck State Park, and offers panoramic views of the Chesapeake Bay.

Hungry folk in North East's downtown area have many choices along Main Street. Locals and visitors flock to Pier One Restaurant for home-cooked Chesapeake and Italian favorites. Shops on Main Street include Kathy's Corner Shop, featuring the works of local artists and selling books by local authors. The 5&10 Antique Market, housed in a late-1800s former hotel, is open every day, and sells vintage collectibles, antiques, jewelry, glassware, and more. Lodging at North Bay Bed and Breakfast is recommended if you want a peaceful, local retreat by the water.

Thurmont

Thurmont, in Frederick County, is just 10 miles from the Pennsylvania border, and known as the "Gateway to the Mountains." Sitting at the foot of the Catoctin Mountains, it is also home to the Presidential retreat, Camp David. Cunningham Falls State Park in Thurmont is the perfect spot to view mountains and waterfalls and hike challenging trails all in one place. The Inn at Springfield Manor sits on a 130-acre estate and offers elegant, comfortable rooms, with breakfast included.

Visitors to Thurmont in October can participate in the Catoctin Colorfest, one of the largest outdoor juried arts and crafts shows on the East Coast. It is free, and features art, crafts, jewelry, food, and beautiful color-changing fall leaves. Stop in Thurmont Kountry Kitchen for comfort food in a family-run diner setting before driving out of town.

Leonardtown

Traveling south in Maryland, you'll come to Leonardtown in St. Mary's County, just across the Potomac River from Virginia. Leonardtown is Southern Maryland's only Arts and Entertainment District, hosting art galleries like North End Gallery, studios, and events such as the Outdoor Art & Movie Night held at Town Market periodically throughout the year.

Leonardtown Wharf Park, sitting on Breton Bay, includes boat slips, a floating dock and a playground, and also hosts concerts and events. The Inn at Leonardtown, a 40-room boutique hotel in the downtown area, is the perfect place to stay to be in the midst of all the action. Dining at The Front Porch is recommended if you want Southern coastal cuisine in a historic home from the 1850s.

Hancock

Hancock, in Washington County, is just two miles from Pennsylvania and two miles from West Virginia. Its most notable feature, the Sideling Hill Road Cut, lies just six miles from town but is a must-see. It was created when Interstate 68 cut through the hill, and includes an exposed 810 feet of strata. Back in town, you can learn more about the history of the area and the Chesapeake & Ohio Canal at the C&O Canal National Historical Park Hancock Visitor Center, housed in a home from 1785.

Buddy Lou's Eats Drinks, and Antiques on Main Street is a place of interest for all ages (you can even bring your dog), featuring two restaurants, shops, and a farmer's market. The best lodging in Hancock is at the 1878 RiverRun Bed & Breakfast, offering views of the Potomac River from its front porch and bicycle storage for hikers and bikers who are traveling the C&O Canal Towpath.

Berlin

Fifteen minutes from the bustling resort town of Ocean City, you'll find the quieter small town of Berlin, in Worcester County. It is known for its Victorian architecture, brick-lined sidewalks, and grand oak trees. Berlin's Main Street served as the filming location for the movies Runaway Bride in 1998 and Tuck, Everlasting in 2001. Staying at The Atlantic Hotel will put you right in the middle of the downtown action, in an 1895 hotel with a Bistro Bar on site.

Beer lovers should tour Burley Oak Taproom & Brewing Company while in Berlin. Downtown Berlin is home to eclectic shops such as British Rose and eateries like the farm-to-table Blacksmith Restaurant, specializing in locally sourced seafood. Unlike restaurants in the busier resort towns, here, you can sit as long as you like and soak in the laid-back atmosphere while enjoying the scrumptious food and drink.

Boonsboro

The Washington County town of Boonsboro sits at the western base of South Mountain, where an important Civil War battle was fought. Just on top of South Mountain, you'll find Washington Monument State Park, the first completed monument dedicated to President George Washington. Book lovers looking for a place to stay in Boonsboro should consider Inn BoonsBoro, which was created and run by author Nora Roberts. All of its eight guest rooms are named after famous literary couples, such as Elizabeth and Darcy from Pride and Prejudice. The bookstore next door is also worth checking out.

Known as one of two towns recognized as an Appalachian Trail Community in Maryland, Boonsboro is the perfect place for hikers to access the trail. Locals will tell you that the town's best feature is the Boonsboro Free Library, with glass walls all around showing off the beauty of Shafer Park and South Mountain. Boonesborough Days, held each September for the past 55 years, is a well-attended event that celebrates the town's handmade crafters and artisans.

Understated, Underrated Charm

Whether you are chasing mountain views, tracking down Hollywood movie history, or relaxing along the waterfront, Maryland's small towns deliver big experiences without the noisy crowds. Exploring places like Havre de Grace, Boonsboro, and Hancock proves that the best travel memories can often be found just off the beaten path. Skip the predictable tourist hotspots the next time you are planning a weekend getaway. Instead, pack a bag, pick a direction, and discover the unmatched local friendliness and underrated charm found in these eight towns that are Maryland's best-kept secrets.