11 Little-Known Towns In Maryland
Maryland is home to 157 self-governing municipalities across its 12,407 square miles of area. Some of the towns in the state are more famous than others. While you may have heard of Baltimore, Ocean City, and National Harbor, there are more small towns in Maryland that are less well-known but that deserve attention. Whether you travel to the mountain village of Oakland in the western part of the state, the waterfront hamlet of Havre de Grace on the Chesapeake Bay, or artsy Leonardtown in the southern part of the state, these towns in Maryland are full of rich history, vibrant culture, and a welcoming, community feel. Take a look at 11 little-known Maryland towns to decide which one you will visit next.
Boonsboro
In Washington County, at the foot of South Mountain, you will find the small town of Boonsboro. The town lies 11 miles south of Hagerstown, and 65 miles west of Baltimore. Founded in 1792, Boonsboro is full of and surrounded by history. Boonsboro is adjacent to the Antietam National Battlefield, and the Boonsborough Museum on North Main Street houses artifacts and items from the Civil War. The town has created a Historic Walking Tour that can be downloaded on Android and Apple phones, to easily guide you around the area. The tour includes the Boonsboro Trolley Museum, a retrospective of the history of trolleys in Boonsboro and surrounding towns. It is housed in the last remaining trolley station in Washington County.
Four miles east of Boonsboro on Alternate Route 40, Washington Monument State Park is at the summit of South Mountain and boasts the 40-foot-high Washington Monument, the first monument dedicated to George Washington's memory. The park also features a picnic area, playground, and museum. Greenbrier State Park, on Route 40, includes a 42-acre man-made freshwater lake perfect for swimming, boating, and fishing.
Readers may recognize the novelist who owns the Inn BoonsBoro, Nora Roberts. Sitting on the square at North Main Street, the inn is a restored historic bed and breakfast that has been owned by Roberts and her husband since 2009. The inn has literature-themed rooms, a gift shop, and Turn The Page bookstore.
You may wish to finish your tour of Boonsboro by stopping at Jeovani's Pizzeria on South Main Street, which serves pizza and Italian dishes in a casual atmosphere. Stone Werks Coffee and Sweets on North Main Street can satisfy your cravings for caffeine and sugar with items including French macarons, tiramisu, and petit fours.
Havre de Grace
"Harbor of Grace," or Havre de Grace, sits where the Susquehanna River meets the Chesapeake Bay in Harford County. This historic town, founded in 1785, pairs natural beauty with history in a delightful way, drawing visitors to its quiet splendor. One of the town's most iconic features is the ¾-mile-long Promenade, running parallel to the Susquehanna River and offers spectacular views of water and wildlife, including ducks, osprey, geese, and bald eagles.
The Friends-Concord Point Lighthouse provides guided tours to visitors from April through October. You may even climb to its top, as long as you are at least 42 inches tall. The Maritime Museum, on Lafayette Street, holds much of the area's environmental and cultural history. Take a walking tour of the town's historic district by picking up a map at the Visitors Center on North Washington Street.
Millard Tydings Memorial Park, on South Washington Street, overlooks the Promenade, the Susquehanna River, and the city's Yacht Basin. Visitors can enjoy its small playground and gazebo, picnic areas, and pickleball courts.
Hungry Havre de Grace residents know to stop by Abbey Burger on North Washington Street. Serving much more than just burgers, the restaurant is open seven days a week. If you feel like something sweet after, head to Bomboy's Homemade Candy on Market Street. In addition to delicious handmade candies, they serve delectable ice cream.
Thurmont
While most people have heard of Camp David, the presidential retreat in Maryland, many do not know that it is located in the small town of Thurmont, at the foothills of the Catoctin Mountains in Frederick County. The town is aptly named, as Thurmont means "Gateway to the Mountains." Thurmont is a designated Main Street Community, and is just 20 miles south of Gettysburg, Pennsylvania.
Thurmont's Main Street has been enhanced to promote pedestrian traffic and tourism. The Main Street Center is a visitor's center and the first stop for many visitors to the town. It sells works by local artists and artisans and souvenirs. Murals on Main Street's former Thurmont Trolley Substation emphasize the natural beauty and community feeling of the town.
The Thurmont Trolley Trail is a one-mile, graded hiking and biking trail between East Main Street and East Moser Road. Four bridges are found along the trail, which was refurbished in 2009. In addition to hiking and biking, birding and photography are also popular pastimes along the trail.
When you have worked up an appetite from your treks around Thurmont, 10Tavern on Main Street serves American fare and alcoholic beverages, lunch, and dinner. The Mountain Gate Family Restaurant, on Frederick Road, features country cooking every day from 8 a.m. to 8 p.m.
North East
A small town on the North East River (which flows into the Chesapeake Bay), North East was the first permanent settlement in Cecil County, in 1658. The town's location along the water draws visitors who want to experience waterfront life, if only for a little while. It is also conveniently about an hour from both Philadelphia and Baltimore.
The North East Branch of the Cecil County Library, on Mauldin Avenue, was recently constructed and is open to visitors and townsfolk alike. A digital media lab, business area, teen area, and children's areas can all be found within this state-of-the-art library, which offers family fun for free.
Elk Neck State Park at the southern end of town contains 2,370 acres between the Chesapeake Bay and Elk River, and is a popular spot for hiking, camping, hunting, and birding. Hike for 1.6 miles from the park to the Turkey Point Lighthouse, which is open to visitors daily year-round.
Main Street North East bestows the perfect small-town experience upon visitors, with a mixture of shops, cafes, and restaurants. Shops such as Kathy's Corner Shop and Silver and Sassy sell unusual items and jewelry, respectively. Chesapeake Bay Coffee Co. is a cute cafe that, in addition to coffee, serves donuts and other baked goods made fresh daily. Restaurants on Main Street to satisfy your cravings include Woody's Crab House, serving Chesapeake seafood; and Steak and Main, a steak house combined with a sushi bar and oyster bar.
Leonardtown
Located in St. Mary's County, in southern Maryland, Leonardtown's breathtaking views of Breton Bay that flows into the Potomac River is just one reason to visit the town. Leonardtown was once a busy port and steamboat landing, and today, it retains the serene, easy feel of a small water-oriented town. It is just 90 miles from Baltimore and 60 miles from Washington, DC.
Leonardtown Wharf Park combines history with outdoor recreation. An exhibit at Tudor Hall within the park explains the town's importance in the War of 1812. The wharf includes a canoe and kayak launch, boat tie-ups, and rentals. The Port of Leonardtown Park houses Mcintosh Run Trail, a water trail running six miles from Leonardtown Wharf Park to Abell's Wharf in lower Breton Bay. Paddlers are often seen along its shoreline.
Leonardtown contains the only Arts and Entertainment District in southern Maryland, covering 100 acres in the walkable downtown area. Shops and galleries such as Craft Guild Shop, North End Gallery, and St. Mary's County Arts Council Gallery and Gift Shop all showcase the work of local artists.
Every October, Leonardtown hosts the National Oyster Shucking Championship at St. Mary's County Fairgrounds. Hungry tourists during other parts of the year should visit The Front Porch or Sweetbay Restaurant and Bar, both on Washington Street.
Chestertown
Settled on the banks of the Chester River along Maryland's Eastern Shore in 1706, Chestertown, in Kent County, is a historic waterfront town that should not be overlooked. Colonial homes along brick sidewalks line its Historic District, and the downtown area is filled with shops, arts, and entertainment.
Chestertown is known as an artist's paradise. Its Arts and Entertainment District includes nine galleries and studios, such as The Artists' Gallery and Garfield Center for the Arts. The Center also sponsors plays at the Prince Theatre, and auditions may be open to the public.
The Historical Society of Kent County in Chestertown has a self-guided walking tour for visitors to help guide them around the town's Historic District. Walking around town, you will notice the wide range of architectural styles, from Georgian to Federal to American Gothic.
Feel hungry or thirsty? Stop by Bad Alfred's Distilling, which serves food as well as alcoholic beverages Wednesday through Sunday. Musicians often perform on the pub's small stage to entertain you while you dine.
Hancock
One of the oldest towns in Maryland, Hancock, in Washington County, was settled in the 1730s. Today, Hancock may be best known for Sideling Hill, a stunning rock formation along Interstate 68 that allows vehicles to travel through it. There is a Welcome Center that you can visit as well, which enables you to take scenic photographs of the breathtaking area.
Hancock has been labeled "Maryland's Trail Town" and houses notable trails, such as the 28-mile-long Western Maryland Rail Trail and the 184.5-mile C&O Canal Towpath. Parks in the town include Widmyer Park, which has sports areas, a branch of the Washington County library, and a playground.
Hancock's Main Street is home to diverse businesses, such as Flannel on the Trail and Hendershot's Sporting Goods. The Blue Goose Fruit Market and Bakery is also quite popular, and not just for its quirky seasonal outdoor decor.
Hungry Hancock visitors should stop at Buddylou's Eats, Drinks and Antiques on Main Street. Here, you can shop, eat, and drink, all in one place. Brunch, lunch, dinner, and ice cream are all served. Bring your dog, as they have a menu just for Fido, too!
Sykesville
Found in Howard and Carroll Counties, Sykesville is just 20 miles west of Baltimore and 50 miles north of Washington, DC. The Main Street of this busy, small town was named the best Main Street in America in 2020 by Independent We Stand.
A walk down Sykesville's Main Street will take you to many shops and boutiques, such as CharlieJoes Clothing Co., Gypsy Systers, and Tidal Salt on Main. If you are looking to improve your health or wellness, stop in Enchanted Karma Wellness and Massage Therapy. Pamper yourself with one of the many salons on Main Street, including Hair by Samsara.
Festivals and events in Sykesville include the Art and Wine Festival in May, the July 4th Parade, the Fall Fun Festival in October, and the Downtown Sykesville Farmer's Market from May through October.
Dining choices are numerous in Sykesville. 7556 Main Street Bistro serves lunch, dinner, and Sunday brunch. If you prefer sweets, stop by The French Twist Cafe on Oklahoma Avenue, where the crepes are to die for.
Oakland
Thousands of tourists visit Deep Creek Lake every year but might not know about Oakland. If you travel past Deep Creek Lake, just 11 miles southwest on Rt. 219, you will come to Oakland, a gem of a town on the border of West Virginia. Sitting in the Appalachian Mountains, at an elevation of 2,451 feet, this town is the farthest west you can go in the state of Maryland.
The Garrett County Historical Museum in Oakland tells the county's history through artifacts from the area. Vehicle aficionados will love the Garrett County Transportation Museum, which houses all types of vehicles. If you are a train lover, the Oakland B&O Museum and Train Station should be to your liking.
Love the outdoors? You will love Oakland. Hike at Swallow Falls State Park, with its 53-foot Muddy Creek Falls. You can then travel 5.5 miles (either by hiking on the trail, or by vehicle) to Herrington Manor State Park, which features the 53-acre Herrington Lake.
In downtown Oakland, don't miss Englanders Antiques Grill and Soda Fountain. This unique store combines an antiques shop with a 1950s-style grill and soda fountain. Englanders serves breakfast and lunch every day, as well as ice cream treats.
Mount Airy
Situated within Carroll and Frederick Counties, Mount Airy is an oft-forgotten small town in Maryland that should not be missed. It is within 40 miles of the Washington, DC and Baltimore areas, and a nice getaway from the busy city.
Historic downtown Mount Airy is easily walkable, and the town's website even provides a handy map to help you find your way around town. One highlight of the area is the Mount Airy Museum, housed within the Historic Train Station on Main Street. A walk through the museum will teach you about the town's history and how the B&O Railroad played a large part in its creation.
Although the town is small, Mount Airy boasts 10 parks within town limits. The most popular park, Watkins Park, encompasses 20 acres between Route 27 and Main Street. It is just a quarter mile from the downtown area. Trails, ball fields, basketball and tennis courts, a playground, and more can be found within Watkins Park.
When you have had enough recreation and are ready to eat, the Mount Airy Inn on South Main Street serves delicious American food and craft beer.
Oxford
The tiny waterfront town of Oxford in Talbot County sits along the Tred Avon River and, founded in 1683, is one of the oldest towns in Maryland. The Oxford Museum on Morris Street contains artifacts from over 300 years of the town's past. The Oxford Custom House, at the intersection of Morris Street and Strand Road, is a replica of a Federal Custom House and is quite interesting for history buffs to explore.
One of the most amazing outdoor experiences in town is a ride on the Oxford-Bellevue Ferry. Started in 1683, it is thought to be the oldest privately owned ferry in the nation still in operation. The ferry takes visitors from Oxford to Bellevue on the Tred Avon River and accepts vehicles, bicycles, and people for its round-trip, 20-minute rides.
Hunger and history meet at the Robert Morris Inn, on North Morris St., which retains part of the original 1710 structure and was the home of a signer of the Declaration of Independence. Chesapeake-American cuisine is on the menu at this waterfront inn, which gives visitors a singular dining experience.
These Towns Deserve Recognition
Hit the roads of Maryland to discover these charming small towns that are new to you. If you opt to visit Oxford, you will enjoy its waterfront, maritime feel. You will marvel at the true engineering feat and beauty of Sideling Hill if you travel to Hancock. A sojourn to Boonsboro will draw you into the town's rich history and sense of community. No matter which of these uncelebrated small towns you choose to visit, you will be sure to discover something new.
