9 Most Neighborly Towns In Maryland
Maryland, a quintessential East Coast state, is known for its coastal views, but it's rich in neighborly communities where hospitality is a way of life. From Chesapeake Bay waterfront towns to mountain retreats and historic main streets, Maryland is full of places where neighbors wave hello, and newcomers are genuinely welcomed. In Easton, weekend farmers' markets bring the town together, while in Boonsboro, hikers and locals cross paths near the Appalachian Trail. Below are nine of the most neighborly towns in Maryland, each offering a sense of community pride, friendliness, and undeniable small-town charm.
Easton
Located in Talbot County on Maryland's Eastern Shore, Easton blends waterfront charm with arts and culture, all within easy driving distance from Baltimore and Annapolis. Sitting on the Tred Avon River, a tributary of the Choptank River, this small waterfront town of just over 17,000 residents was founded in 1710 as Talbot County's county seat.
Easton has something for everyone. The Talbot Historical Society details the history of the town and the county. The Academy Art Museum is open daily with free admission and hosts the works of local artists. Easton is also home to many neighborly festivals and fairs, such as the Waterfowl Festival, an international celebration of waterfowl art that attracts thousands to the town each November. Every Saturday year-round, townsfolk gather on Harrison Street at the Easton Farmers Market to buy produce and baked goods from local growers and arts and crafts from local artisans.
Chestertown
One of Maryland's oldest towns, founded in 1706, Chestertown was known as "Newtown" and was a historically significant colonial port. It sits on the Eastern Shore in Kent County and was one of just six “Royal Ports of Entry” to the state during colonial times. Today, the town of about 5,500 has a historic district that includes the Custom House, circa 1746, and Memorial Park, which honors Kent County residents lost in various wars. Honoring townsfolk and county residents who have served to defend our country is one of the most neighborly aspects of Chestertown.
Chestertown's renowned Arts and Entertainment District is filled with galleries, including Chestertown River Arts on High Street. Even some of the town's annual events have a historic theme. One of Chestertown's most popular annual festivals, the Chestertown Tea Party Festival, is held each May and reenacts the town's famous Tea Party of 1774. Town residents and visitors attend each year and partake of the food, entertainment, and activities offered.
Havre de Grace
Housing just under 15,000, the "harbor of Grace," Havre de Grace sits along the Susquehanna River where it empties into the Chesapeake Bay. It is within easy driving distance to Baltimore and is a charming, historic waterfront town that cherishes its small-town, welcoming atmosphere. Founded in 1782, the town was renamed from Susquehanna Lower Ferry to Havre de Grace in honor of General Marquis de Lafayette, who mentioned that the town reminded him of Le Havre, a French seaport.
With such neighborly historic beginnings, recognizing help from our French allies, it's no wonder that Havre de Grace is known for its neighborliness today. Lafayette's legacy is still remembered today, as the town conducts Historic Havre de Grace Walking Tours covering the "Lafayette Trail." The Historical Society of Harford County also periodically hosts concerts featuring Music from the Life and Tour of Lafayette. Other town events include the Havre de Grace Ice Festival, held each February, and the Susquehanna Wine & Seafood Festival, occurring each September at the Concord Point Lighthouse.
Leonardtown
The small town of Leonardtown, population about 4,500, in St. Mary's County, is an easy drive from our nation's capital, Washington, DC. One of Maryland's oldest towns, founded in 1708 as "Seymour Town," on Breton Bay, this rural community in southern Maryland is full of arts, culture, and nature. The Leonardtown Butterfly Trail is one of the most creative ways to explore Leonardtown, as it highlights historic landmarks, art galleries, and outdoor spaces of interest to residents and visitors.
Leonardtown Wharf Park sits on Breton Bay and offers opportunities for strolling, paddleboarding, and simply sitting to admire the view. In the summer months, neighbors and visitors gather in the park for the Leonardtown Summer Music Festival and Fourth at the Wharf Event and Concert on the Fourth of July. Shops and small businesses along Leonardtown Wharf include Frog Town Ice Cream. Leonardtown's community spirit shines through in its defining small-town events and friendly small businesspeople.
North East
One of Maryland's oldest towns, North East in Cecil County, was settled in 1658. It sits at the headwaters of the North East River and is an easy drive from both Philadelphia and Baltimore. Home to about 4,000 residents, North East's small-town charm and walkable downtown area, combined with its friendly community, make it one of the most neighborly towns in Maryland.
Main Street in North East is easily walkable, featuring shops like 5 & 10 Antique Market and coffee houses including Chesapeake Bay Coffee Co. Restaurants serving local seafood dot Main Street, with Woody's Crab House among the most visited. North East Community Park in town hosts events year-round, its most popular being the Salute to Veterans Festival & Fireworks held each July 3. North East's sense of community spirit keeps townsfolk in the area and attracts visitors to return time and again.
Mount Airy
Sitting within two counties (Frederick and Carroll), the small town of Mount Airy, with a population just under 10,000, has a welcoming downtown that serves as a natural gathering place for friends and neighbors. It is within an hour's drive of Baltimore, and just 20 minutes from the larger city of Frederick. Mount Airy was founded, nameless, in the 1830s alongside the construction of the Baltimore & Ohio Railroad line. It is said that an Irish railroad worker complained of the cold air in the town and suggested the name Mount Airy. Neighbors agreed, and the town was renamed Mount Airy.
Such an auspicious beginning, with neighbors settling on the town's name together, bodes well for Mount Airy's friendliness going forward. The Historical Society of Mount Airy Museum, located in the Train Station on Main Street, tells much of the town's long history. Today, neighbors and visitors meet weekly, on Wednesdays from May through September, at Mount Airy Farmers Market, to buy local produce, arts, crafts, and more. Mount Airy Inn on the town's Main Street brings folks together for food and drink year-round, known for its delicious pizza & microbrews. Each August, the Celebrate Mount Airy festival is held on Main Street, drawing townspeople and 2,500 visitors to the small town. The event features a block party, car show, and live music, so there is something fun for everyone.
Boonsboro
Nestled at the foot of South Mountain of the Appalachian Mountains in Washington County, Boonsboro is Maryland's first designated Appalachian Trail Community. Founded in 1792, the town is just 10 miles south of Hagerstown and within easy driving distance of Baltimore. Its gorgeous mountain scenery and close-knit community help make Boonsboro, with a population of about 3,500, one of Maryland's most neighborly towns.
Hikers and mountain lovers can access the Appalachian Trail in multiple places in Boonsboro, one of the most popular being South Mountain State Park. The 7,700-acre park also offers scenic overlooks, camping spots, and hunting areas, providing endless opportunities. Back in town, the Boonsboro Trolley Museum, housed in the last remaining trolley station in Washington County, is where townsfolk and visitors go to learn more about Boonsboro's history. Neighbors come together at the Boonsboro Farmers' Market on Potomac Street every Tuesday from May through October. One of the town's most popular annual events is the Boonsboro Food Truck Festival, held in Shafer Park each September, drawing residents and outsiders to sample a variety of foods from food trucks and local vendors.
Oakland
One town in western Maryland that is the epitome of small-town charm is the Garrett County seat of Oakland. Home to almost 2,000 residents, Oakland abuts the West Virginia border and is a self-contained, walkable small town. The town was founded in 1849 as a planned stop along the upcoming B&O Railroad. Everything a resident could possibly need is within walking distance, from the Ruth Enlow Library on Second Street to the historic Garrett County Courthouse, circa 1907, on Fourth Street.
Oakland's small-town atmosphere extends to its businesses, one of its most popular being Englander's Antiques Grill & Soda Fountain on Alder Street. Here, townsfolk and visitors can browse through antiques and enjoy breakfast, lunch, or an ice cream treat. Oakland's most famous annual event is the Autumn Glory Festival, held each October. This five-day celebration of fall foliage features parades, art, activities, concerts, food, and fun. The natural beauty of Oakland is on display at this festival, which also highlights the city's friendliness.
Hancock
Dating to the 1730s, the Washington County town of Hancock was named after a Revolutionary War hero and resident Edward Joseph Hancock, Jr. The town of about 1,500 people sits at the northernmost point of the Potomac River, at the narrowest part of Maryland that is sometimes referred to as "Maryland's Waist," a mile-wide strip between Pennsylvania and West Virginia. It is within easy driving distance of the larger towns of Cumberland and Frederick, and is known for its rich history, natural beauty, and friendliness.
All of Hancock's parks are within walking distance of restaurants and stores, which increases the neighborliness of the town. The Western Maryland Rail Trail runs alongside the Chesapeake & Ohio Canal Towpath and offers townsfolk and visitors miles of hiking and biking. History lovers should check out the Historic Bowles House and Visitor Center, housed in a 1780s farmhouse and featuring exhibits on the town's canal history. The Two Mile Music Fest is an annual event held in Kirkwood Park each August, drawing local and nationally known musical acts. Buddy Lou's Farmer's Market is held on Saturdays on Main Street in Hancock, bringing neighbors and visitors together to browse local produce, baked goods, and gifts.
Neighborly Municipalities in Maryland
Across Maryland, from the eastern shore to its western mountains, you will find neighborly communities such as these, offering a variety of fun, friendly activities for all ages. While strolling down a historic Main Street, enjoying waterfront sunsets, or attending local festivals, you will feel the sense of connection, hospitality, and community pride that the residents of these Maryland towns value. These qualities make residents proud to call these towns home.
