10 Small Towns In Maryland With Big Charm
Maryland is well-known for its bustling cities and iconic waterfronts, but beyond these usual routes lie small towns bursting with charm, character, and community spirit. These hidden gems offer a refreshing escape from the fast lane. In these towns, historic main streets, scenic landscapes, and friendly locals are found. Whether you are seeking a weekend getaway, a new hometown, or just a drive to visit somewhere new, these small towns prove that big charm often comes in the smallest packages.
Chestertown
The Kent County town of Chestertown, on the Chester River on Maryland's Eastern Shore, is one of the state's oldest towns, founded in 1706. Today, its brick sidewalks are filled with charming shops, food, arts, and culture. Its small-town atmosphere is bolstered by its many annual festivals and events. The Chestertown Tea Party Festival is held each Memorial Day weekend, celebrating the town's own Revolutionary Tea Party in 1774. History about the area can be gleaned by visiting the Historical Society of Kent County. Chestertown's Arts & Entertainment District includes eclectic venues such as the Garfield Center for the Arts on High Street, which puts on live performances and shows current and classic films. The area's best, freshest food is sold at the Chestertown Farmers and Artisans Market, held every Saturday year-round.
Berlin
Just 10 miles from the resort town of Ocean City, Berlin was named the "Coolest Small Town in America" in 2022 by Baltimore Magazine. This Worcester County town is brimming with charm, as evidenced by its usage as a filming location in two major motion pictures, "Runaway Bride" in 1998, and "Tuck, Everlasting" in 2001. Berlin is a town steeped in history, art, and the beauty of the Eastern Shore.
Berlin's historic district comprises 47 structures. One of them is the Calvin B. Taylor House, a historic museum on Main Street that will enlighten you more on the town's history. Berlin's historic Globe Restaurant & Bar is actually the renovated Globe Theater, which, today, serves up movies, food, and drink. Art lovers can participate in the Second Friday Art Stroll, held year-round in downtown Berlin, when shops and restaurants stay open late while visitors and residents check out art from local artists. If you want to be surrounded by nature, head 10 miles from Berlin to the Maryland entrance of Assateague Island National Seashore. The 37-mile-long barrier island is filled with birds and wild horses, as well as other wildlife, and is a quiet, serene place to enjoy the outdoors.
Stevensville
The unique small town of Stevensville, founded in 1850, sits at the eastern end of the Chesapeake Bay Bridge, and is the first stop on Kent Island after crossing the Bay Bridge. This quaint waterfront town offers some of the most scenic views of the Chesapeake Bay. Stevensville has a large historic district, arts area, and busy downtown shops and eateries that make it an interesting town to visit.
Historic Stevensville, listed on the National Register of Historic Places, is open to the public on the first Saturday afternoon of each month. One of the sites that can be toured is the Stevensville Train Station and Caboose, now vacant, which was once a stop on the rail service from Queenstown to Lewes, Delaware. The Kent Island Federation of the Arts in Stevensville is an art gallery and exhibition site that was opened in 1963 to make the arts accessible to residents of the island. To see even more of the natural beauty of the area, visit Terrapin Nature Park, with 276 acres of meadows, wetlands, woodlands, and shoreline, and a 3.25-mile walking trail. The town comes together each year on the third Saturday in May to celebrate Kent Island Day, commemorating the island's founding in 1631 with a parade, exhibits, displays, music, food, and more.
Easton
The Talbot County town of Easton lies halfway between Baltimore and Ocean City, and contains boutiques, art galleries, restaurants, and a large historic section. The town's website notes that it has been called the "8th Best Small Town in America," and its older homes with large porches, tree-lined streets, and a busy downtown area make visitors to Easton feel comfortable.
The town's historic Avalon Theatre, built in 1921, was restored to its original Art Deco style in the 1980s. Now, the 400-seat theatre features live performing arts, community events, and educational programs. The arts are celebrated at Plein Air Easton each July, the largest and most prestigious juried plein air painting competition in the US. Thompson Park, in the heart of the downtown area, is a community square with benches and public art displays that also hosts live music performances and festivals. While in Easton, be sure to visit the Pickering Creek Audubon Center, comprising 400 acres of forests, fields, and tidal marshlands, with four miles of trails for hiking.
Cumberland
The Western Maryland town of Cumberland is enjoying a renaissance, as it has just undergone a renovation to its downtown area. Called the "Queen City," Cumberland was once the second-largest city in the state (Baltimore being the largest). The Allegany County town of Cumberland is a gem sitting in a valley in the Appalachian Mountains, rich in arts, culture, history, and beauty.
Cumberland's downtown area is historic and artsy at the same time. This walkable area is home to a variety of galleries, such as the C. William Gilchrist Museum of the Arts, and historic landmarks, including the Gordon Roberts House, home to the Allegany County Historical Society. Check out River Park at Canal Place, a waterfront park area that is currently being transformed into a much larger outdoor recreational site. Hikers and bikers can get some exercise along the C&O Canal Towpath, running from Cumberland to Washington, DC, and providing not only outdoor exercise but also more than 1,000 historic structures and 200 rare and threatened species of plants and animals along its route.
Pocomoke City
The Southern Maryland town of Pocomoke City in Worcester County is just a few miles north of Maryland's border with Virginia, and its Chamber of Commerce touts it as "the friendliest town on the Eastern Shore." Sitting along the Pocomoke River, Pocomoke City is just 30 miles from Ocean City and holds much history in its streets. This town's natural beauty and community feel add to its charm.
Visit the Sturgis One Room School Museum, a historic school from 1900, honoring the history of African American education. Pocomoke City's historic Mar-Va Theater Performing Arts Center hosts live performances, films, and events. Cypress Park along the town's waterfront features a 1.5-mile nature trail featuring exercise stations, a floating boardwalk, and a fishing pier. Downtown Pocomoke hosts Fourth Fridays every Friday evening from spring through fall, in which food trucks, artisan vendors, live music, and residents gather to enjoy all that their community has to offer.
Havre de Grace
The Harford County town of Havre de Grace (French for "Port of Grace") sits along the Susquehanna River in northern Maryland, at the top of the Chesapeake Bay. Named by the Marquis de Lafayette in 1782, the town was incorporated in 1785, making it the second-oldest town in Maryland after its capital city, Annapolis. Today, this town is still full of grace, charm, and history.
The Lafayette Trail loops for three miles through Havre de Grace, starting at the Lockhouse Museum in North Park and winding through its historic district. Walking this trail is a great way to get exercise and see the town's history. The Concord Point Lighthouse, built in 1827, is the oldest publicly accessible lighthouse on the Chesapeake Bay, and can be visited on weekends. For a different type of history, visit Bahoukas Antique Mall and Beer MuZeum, featuring a wide array of antiques as well as beer and alcohol related artifacts. The town holds many annual events, including Christmas at the Park, held at Tydings Park in December, complete with caroling, hot chocolate, and Santa Claus.
Oakland
Located in the Appalachian Mountains in southern Garrett County, the small town of Oakland is about 20 minutes from the popular tourist site, Deep Creek Lake. Visitors to Deep Creek Lake only need to stay on Route 219 for 20 more minutes heading south to reach the charming town of Oakland. It is a destination that is definitely worth the short drive.
Oakland and the area's history is explored at the Garrett County Historical Society Museum in the small town's bustling downtown area. The Garrett County Arts Council is responsible for the town's many events and art programs, including the Artist Studio Tour, held in July. Oakland's most popular annual event is the Autumn Glory Festival, held for five days each October, celebrating the gorgeous fall foliage of the area. Hikers should check out the Swallow Falls Canyon Trail, a 1.1-mile-long trail in Swallow Falls State Park, that passes four breathtakingly beautiful waterfalls.
Parkton
The northern Baltimore County town of Parkton is just five miles south of the Pennsylvania state line, adjacent to York County, Pennsylvania, along the Mason-Dixon Line. This small town is historic, first settled by Europeans in the 1700s. Parkton's rural setting, among rolling hills and serene beauty, combined with its proximity to Baltimore, which is just 35 minutes away, makes it a charming suburb in which to get lost for a while.
Hill House, on the National Historic Register, is one of Parkton's most famous historical landmarks, also known as Cool Spring. This house, circa 1879, was built for a local physician and still stands as an example of Second Empire architecture in the modern era. BeeTree Preserve is 260 acres of meadows and forest, home to many wildlife species, hiking areas, pavilions, and campsites. Gunpowder Falls State Park features 120 miles of trails for hiking, biking, and horseback riding. Wine lovers should check out Royal Rabbit Vineyards, a family-owned winery in Parkton that offers tastings and event space.
Bel Air
Just 45 minutes north of Baltimore in Harford County, the town of Bel Air today is a mecca for shoppers, but was once a stop along the Underground Railroad. The county seat of Harford County since 1782, Bel Air is packed with charm, history, and modern amenities that make it a one-of-a-kind small town.
The Hays-Heighe House on Harford Community College Campus was the first place in Harford County to be put on the National Underground Railroad Network to Freedom. The public can tour this important landmark in history. Bel Air's Arts and Entertainment District runs a Public Art Tour through the town, where visitors can explore public art over two miles across the town. The town of Bel Air is known for its markets as well as its shopping, and the Belle Aire Holiday Market in December is one example. This open-air market features artisan items, crafts, and antiques. Bel Air's Historic District is filled with unique, independently-owned shops, like The Nest on Main Gift Shop. Those who prefer big-box stores have their pick from four shopping malls in Bel Air: Harford Mall, Tollgate Marketplace, Bel Air Plaza, and Bel Air Town Center.
Small Towns, Big Hearts
These 10 small Maryland towns are loaded with charm, community spirit, history, and beauty. While not as flashy or crowded as the big city, small municipalities in Maryland offer even more than that: a real sense of belonging. Whether you want to visit a waterfront town, a mountain village, or a suburban hamlet, these towns provide a window into the state and the nation's history. Surrounded by natural beauty, a visit to any of these Maryland towns is a great way to relax, unwind, and discover something new.
