12 Of The Friendliest Towns In Maryland
Maryland may be small in size, but it's big on charm, especially when it comes to communities where friendliness is a way of life. With waterfront villages, historic main streets, and close-knit mountain towns, Maryland is filled with places where neighbors still wave hello, and newcomers are welcomed with genuine warmth. Here, we highlight 12 of the friendliest towns in Maryland, each offering its own unique blend of hospitality, community spirit, and small-town charm that makes visitors feel at home and residents proud to call it their own.
Thurmont
Sitting at the foothills of the Catoctin Mountains in Frederick County, the town of Thurmont is 20 miles south of Gettysburg, Pennsylvania. It is known as the "Gateway to the Mountains," and also as the home of Camp David, the famous presidential retreat. Thurmont's friendliness can be seen in its inclusion as a designated Main Street Community, with a downtown area that is very pedestrian-friendly.
Catoctin Wildlife Preserve and Zoo in Thurmont, open from the end of March to two days before Christmas, is a 50-acre park filled with wildlife, ponds, and beautiful landscaping. Visitors can experience interactive educational programs that help them better understand wildlife and conservation. Those interested in hiking should visit Cunningham Falls State Park. The park consists of over 6,100 acres. Of its two areas, the William Houck Area contains the Falls Trailhead, with a 2.8-mile nature trail. Its lower trail, just 0.5 miles, leads to the stunning falls. The second weekend every October, Thurmont's downtown area hosts the Catoctin Colorfest, a festival that draws 100,000 visitors and includes food, crafts, and art from local vendors. Locals and visitors also gather regularly at Thurmont Kountry Kitchen downtown for country-style, relaxed meals.
Havre de Grace
The "port of grace," Havre de Grace marks the spot where the Susquehanna River meets the Chesapeake Bay in Harford County. This historic, waterfront town is just 40 miles from Baltimore. Havre de Grace has a communal, friendly atmosphere that keeps visitors coming back again and again, with some even opting to settle down there instead.
One of the most historic landmarks in Havre de Grace is the Concord Point Lighthouse, the second-oldest lighthouse in Maryland, established in 1827. Open to the public weekends only from April through October, the lighthouse also hosts special events. Visitors who are art lovers should check out the town's Arts and Entertainment District, which includes Arts by the Bay gallery, featuring works by a diverse array of locals. The district also hosts 225 events and 22 festivals annually, including "It's Lit!" Book Readings on the third Friday of each month at St. John's Episcopal Church, bringing people of all ages together. MacGregor's Restaurant, also on St. John's Street, is the perfect place to enjoy local seafood and awe-inspiring views of the Susquehanna River for lunch or dinner.
North East
The Cecil County community of North East is at the headwaters of the North East River, one of the tributaries flowing into the Chesapeake Bay. One of the oldest towns in Maryland, it was settled in 1658. North East is about 40 minutes from Wilmington, Delaware and just an hour north of Baltimore.
The town's Main Street is an inviting, friendly road filled with shops, such as Silver and Sassy jewelry, and eateries, including Woody's Crab House, that attract visitors year-round. North East hosts many community events that bring people together, such as Valentine Carriage Rides on Valentine's Day. The annual Salute to Veterans & Fireworks Show, held each year on July 3 in North East Community Park, is another popular event that draws thousands of visitors to this small riverside town. It features live music, food, and fireworks that rival those of many neighboring small towns.
Boonsboro
Washington County's town of Boonsboro is at the foot of South Mountain, 11 miles south of the larger city of Hagerstown and 65 miles west of Baltimore. Founded in 1792, Boonsboro's history, community feel, and natural beauty draw many to this small village amidst the mountains. It is the first Appalachian Trail Community in Maryland.
Those wishing to hike the Appalachian Trail need to head only a few miles east of town to access it, at Washington Monument State Park. The park also includes the first Washington Monument, standing 34 feet high and built by Boonsboro townsfolk in 1827. To learn more about the history of the town, take the self-guided Historic Walking Tour, including a stop at the Boonsboro Trolley Museum, which is housed in the county's last remaining trolley station. The town holds its Annual Rescue Company Carnival in Shafer Park at the end of May, featuring food, rides, music, and fun for everyone. Branded Chophouse in town is an eatery with a laid-back atmosphere, well-suited for enjoying food while in the company of others.
Oakland
Oakland is one of the westernmost towns in Maryland, located in Garrett County just 10 miles from the West Virginia border. This mountain town in the Appalachians sits at an elevation of 2,451 feet and features historic sites, a welcoming downtown area, and breathtaking natural beauty. It is just over 100 miles south of Pittsburgh, Pennsylvania.
History and automobile lovers should start their tour of Oakland at the Garrett County Transportation Museum, which, in addition to housing sleighs, carriages, buggies, and automobiles, features exhibits on nearby Deep Creek Lake and Maryland State Parks. Visitors can hike in Swallow Falls State Park, nine miles north of town, and check out its awesome 53-foot high Muddy Creek Falls. Those who wish to shop and eat in the same spot should visit the downtown Englander's Antiques Grill and Soda Fountain, a welcoming, 75-year-old establishment that sells consigned antiques, milkshakes, buckwheat cakes, breakfast, and lunch. Each October, Oakland hosts the annual Autumn Glory Festival, now in its 59th year. Attracting thousands to the town, this festival celebrates the area's beautiful foliage and features a parade, musical competitions, and driving tours.
Easton
The Talbot County town of Easton is a small town east of the Chesapeake Bay that is easily accessible from Baltimore (about an hour and a half drive) and Annapolis (just under an hour's drive). Founded in 1710, Easton is filled with history, charm, art, and culture, beckoning those who are searching for a quaint small town. Its position at the headwaters of the Tred Avon River, a tributary of the Choptank River, gives the city a unique waterfront feel.
The Talbot Historical Society in Easton is a great place for history lovers to start a tour of the town. The historical center includes three galleries of the county's history as well as an antique shop. Art enthusiasts should check out the Academy Art Museum, open daily with free admission, featuring exhibits by local and regional artists. Each November, Easton hosts the Waterfowl Festival, now in its 55th year. This celebration of waterfowl art draws thousands of visitors and raises awareness of wildlife conservation. Visitors enjoy a variety of activities, including food, crafts, exhibits, and demonstrations. Food and drink can be enjoyed any time of the year at Legal Assets Craft Food and Spirits in Easton's downtown area.
Sykesville
Sykesville is just 30 miles from Baltimore and spans two counties, Carroll and Howard. This small town is also 50 miles north of Washington, DC, and is a favorite of many living in those larger cities who want to get away from the hustle and bustle for a while. Sykesville is filled with natural beauty, friendliness, and quietude that can't always be experienced in the big city.
The Gate House Museum in town is a great place to learn more about Sykesville's history and its founder, James Sykes. Sykesville's Global Mural Mosaic Program, unveiled in 2024, celebrates the beauty of community and individuality and is part of a larger worldwide program. Sykesville hosts its Fall Fun Festival each October on Main Street, featuring face painting, mimes, crafts, food, and entertainment. You can also enjoy food and spirits at E.W. Becks Pub and Restaurant, located on Main Street, which serves local seafood, coffee, and specialty cocktails.
Mount Airy
Another town that straddles two counties, Mount Airy is in Carroll and Frederick Counties. At just under an hour from Baltimore and only 20 minutes from the city of Frederick, the charming small-town atmosphere of Mount Airy, combined with its historic downtown, makes it the ideal spot to relax, recharge, and enjoy the company of family and friends.
The Caboose Visitor Center on Mount Airy's Main Street is a retired C-2095 Caboose, retired from service in 1978, and is now used as a museum and the centerpiece for town events. Mount Airy Rails to Trails, also known as the Old Main Line Trail, is a mile-long paved trail that runs along a former B&O Railroad through town, perfect for exercise or exploring the town's unique character. Mount Airy Inn on Main Street is a great gathering spot that serves American food and local craft beer, and the Mount Airy Farmers Market brings people together on Wednesdays from May to September. Vendors at the market sell local and regional produce, crafts, meats, eggs, wines, and more.
Hancock
Washington County's Hancock is one of Maryland's oldest towns, settled in the 1730s. This small town features outdoor recreational opportunities, small businesses, arts, and natural beauty, along with friendly townsfolk. Hancock sits between Cumberland (40 miles to the west) and Frederick (55 miles to the east).
Hikers and bikers might want to check out the Western Maryland Rail Trail, running 28 miles beside the C&O Canal Towpath. Flannel on the Trail is a one-of-a-kind shop showcasing the works of local artisans, selling home decor, offering workshops, and even serving as an event venue. Triangle Restaurant on Main Street serves American fare in a friendly atmosphere. One of Hancock's most popular events is its Halloween Parade, now in its 79th year. Both locals and visitors from elsewhere travel toward downtown to participate in this annual event.
Chestertown
Kent County's town of Chestertown was founded along the banks of the Chester River in 1706. Chestertown has something for everyone, including history, the arts, fresh seafood, and waterfront beauty. It is also the home of Washington College, founded in 1782 and the first college chartered in the sovereign United States.
Chestertown's Arts and Entertainment District includes galleries such as the Garfield Center for the Arts, a performing arts venue in the downtown area. To learn more about the town's rich history, stop by the Historical Society of Kent County for a self-guided walking tour of the town's Historic District. Bad Alfred's Distilling on High Street serves wood-fired pizzas, house-made spirits, and local craft beer, providing a gathering place for locals and visitors. Each May, Chestertown hosts its annual Chestertown Tea Party Festival, reenacting the town's 1774 tea party and featuring a variety of food, drink, crafts, and activities suitable for all ages.
Leonardtown
Located in St. Mary's County in southern Maryland, Leonardtown is a friendly, walkable town filled with history and a bustling downtown area. It also houses the only Arts & Entertainment District in Southern Maryland. Leonardtown is about 55 miles from Washington, DC, and just a few miles across the Potomac River from the Virginia border.
Leonardtown Wharf is a beautiful waterfront area with space to walk, paddleboard, or hold an event. Free concerts are held here in the summertime, at the Leonardtown Summer Music Festival, from June through August. Leonardtown's Arts & Entertainment District spans 100 acres of the downtown area and features the St. Mary's County Art Council Gallery and Gift Shop, showcasing and selling works by local artists. The Front Porch Restaurant, located on Washington Street, serves Southern cuisine, craft beer, and cocktails in a historic home featuring a large front porch, perfect for dining in warmer weather. It is one of the best spots in town to enjoy a meal with friends.
Elkton
The county seat of Cecil County, Elkton sits along the Elk River at the northern headwaters of the Chesapeake Bay. The town borders Delaware, offering easy accessibility to Wilmington (a 30-minute drive away), Baltimore (approximately an hour away), and Philadelphia (just over an hour away from Elkton). Elkton combines historical charm, a busy downtown area, and opportunities for outdoor recreation in a friendly atmosphere.
The Historical Society of Cecil County is on Main Street in Elkton and offers a glimpse into the town's significance in the Revolutionary War and the War of 1812. The Fair Hill Natural Resources Management Area spans 5,600 acres and features walking and horseback trails, as well as an environmental education center. Each September, Elkton hosts its annual Fall Fest, a community event including music, food, and fun. Dining options in Elkton's downtown area include C3ntral Tavern on Main Street, serving American comfort food with a full-service bar. Locals and visitors can often be found gathering here to watch sporting events together.
Cordial Communities in Maryland
From the coastal eastern part of the state to its western mountains, Maryland is filled with cordial communities that offer a variety of fun and friendly activities for visitors, newcomers, and long-term residents. Whether you enjoy strolling down a quaint Main Street, hiking in the mountains, or participating in water-oriented activities, these 12 small towns in Maryland are some of the friendliest that you will encounter anywhere.
