11 Picture-Perfect Main Streets In Maryland
Main Street Maryland is a program run by the Maryland Department of Housing and Community Development that is aimed at revitalizing and strengthening the economic potential of Maryland's small towns' downtown areas. Many, but not all, of these most picture-perfect streets in Maryland are part of the Main Street Maryland program. Whether strolling down the sidewalks of Berlin or the waterfront in Havre de Grace, visiting these towns and their Main Streets or downtown areas will give you a sense of community, history, culture, and belonging.
Berlin
The small town of Berlin in Worcester County is home to just over 5,000 people. Its Main Street has often been recognized, most recently by Main Street America, which named Berlin's Main Street as one of the best in the country for building a strong, vibrant community. Additionally, USA Today named Berlin and its Main Street one of its "Best Towns for Shopping" in 2018 and 2020. The historic shore town's Main Street is filled with more than 60 shops, such as Outten's Delites and Victorian Charm, and eateries, including The Sterling Tavern and Blacksmith.
Berlin's Main Street is so picture-perfect that it was used in two films in recent years. 1998's "Runaway Bride" was filmed with Main Street Berlin as a backdrop, transforming the town into the fictional Hale, Maryland. 2002's "Tuck, Everlasting" was also filmed in Berlin, with the tree-lined Main Street becoming the fictional Treegap. You must see Berlin's Main Street for yourself to grasp the charm of this picturesque town.
Sykesville
Not only was Sykesville's Main Street been named "Best Main Street in America" in 2020 by Independent We Stand, but it has also been recognized by the National Main Street Program for its revitalization. The town, located in Howard and Carroll counties, is home to just over 4,300 people, and was named the "Coolest Small Town in America" in 2016 by Budget Travel magazine. Sykesville is convenient to both Washington, DC, which is 40 miles away, and Baltimore, just 30 miles away.
A variety of shops, restaurants, and attractions line Sykesville's Main Street, which is not far from the Patapsco River. A Historical Tour of Downtown Sykesville might be your cup of tea, if you are interested in the history of the town. This starts at the Town House or Visitor's Center. Shoppers have their pick of shops on Main Street, including Park Books on Main. When hunger strikes, check out the many eateries such as 7556 Main Street Bistro.
Oakland
Although the Garrett County village of Oakland, home to just over 1,800 folks, doesn't have a Main Street, it has been designated a Main Street Maryland Community. The town's streets and businesses follow the "Main Street Approach," founded upon broad-based community engagement, understanding quality of life factors, and a focus on economic vitality, quality design, effective promotion, and sustainable organization. Second Street, Third Street, and Alder Street are full of historic buildings housing businesses, shops, and restaurants. The town is surrounded by the Appalachian Mountains.
The Garrett County Historical Society on Second Street offers walking tours of Oakland and is a great place to start exploring the town's roots. Englander's Pharmacy, Antiques & Fountain on Alder Street combines shopping for antiques and knick-knacks with a 1950s-style fountain and grill, so you can shop while you eat! Book lovers should check out The Book Mark'et on Second Street. Smoke N Mirrors Gallery on Third Street is perfect for those searching for original photographs of the area.
Havre de Grace
Another town without a "Main Street" but retaining that Main Street picturesque feel is Harford County's Havre de Grace, home to just over 14,800 people. The community is a designated Main Street Maryland Community, and its downtown area is filled with art galleries, shops, and eateries. A peaceful Promenade boardwalk along the Susquehanna River provides an area for walking and nature-watching.
Shops such as Anita's Treasures on St. John Street sell uniquely curated goods. Arts By the Bay, An Artists' Cooperative Gallery, also on St. John Street, is a space full of original works by regional artists. Strolling this quaint, historic town can work up an appetite. When it comes to dining choices, there are many, including the well-known MacGregor's, serving local seafood and more on St. John Street.
Cumberland
Cumberland is situated in a river valley in the Appalachian Mountains of Allegany County. This historic town of just under 20,000 people has 27 listings on the National Register of Historic Places, and has evolved with a vibrant downtown area filled with shops, art, and eateries. Canal Place Heritage Park on Canal Street is home to a Visitor's Center as well as other historic sites and is a perfect place to start your tour of Cumberland.
The Arcadian on Baltimore Street downtown houses an art gallery, a lounge, and an events space. Downtown shops like Myla & Maple on North Centre Street offer eclectic vibes and styles for many to enjoy. Mezzo's, on South Centre Street, is the perfect place to unwind with a cocktail and savor a tapas-style menu after a day spent walking around Cumberland.
Leonardtown
Leonardtown is home to the first Main Street Maryland designated Main Street in St. Mary's County. The small town, population just over 4,500, is also home to the only designated Arts & Entertainment district in Southern Maryland. The heart of Leonardtown's historic district is its Leonardtown Square, housing a two-sided World War I Memorial including the names of 27 St. Mary's County residents who died during the war.
Leonardtown also boasts many retail businesses, from galleries like North End Gallery on Fenwick Street, to boutiques such as New View FiberWorks on Washington Street. If all that shopping makes you hungry, there are many eateries from which to choose in Leonardtown. The Front Porch on Washington Street is a local favorite, specializing in Southern fare, cocktails, and craft beer served in a historic home with porch seats.
Thurmont
Another designated Main Street Maryland community, Thurmont, in Frederick County, is home to just over 6,000 residents. This historic small town, just 15 minutes south of Gettysburg, Pennsylvania, and an hour from Baltimore and Washington, DC, is filled with family-owned restaurants and independent shops. In addition to the many businesses on Main Street and in the town square, the town hosts signature events each year, like Plein Air, held each September as a gathering of artists painting outdoor subject matter.
Shops that you should check out in Thurmont include Thurmont Main Street Arts & Gifts, on Water Street, and Studio 24E, showcasing local artisans, on Main Street. Thurmont Kountry Kitchen on Water Street is a great place to stop for country, home cooking in a relaxing atmosphere. All of this can be experienced against the backdrop of the beautiful Catoctin Mountains, which surround the town.
Chestertown
The Eastern Shore town of Chestertown, population just over 5,500, is part of the Main Street America program and Main Street Maryland, both of which fuel Main Street Historic Chestertown. With around 300 historical landmarks and plenty of downtown businesses, Chestertown's downtown is thriving. The small town on the Chester River in Kent County is home to many interesting historic and contemporary sites. The Chestertown Visitor's Center on the corner of Maple Avenue and Cross Street is the perfect place to start your tour of this unique town.
When it comes to shopping in downtown Chestertown, there are many stores worth exploring. Bart's Records on Cannon Street and Bespoke Chocolate on Cross Street are just a few. If you decide to eat at Bad Alfred's Distilling Co. on High Street, you may choose to sample house-made spirits, local craft beer, and wood-fired pizzas. Most, if not all, merchants accept Chestertown Cash, a unique and convenient digital gift card program designed just for the businesses in the downtown area.
Easton
The county seat of Talbot County, Easton, population just over 17,000, was named one of America's 10 Best Small Towns in 2025 by Country Living Magazine and is another Main Street Maryland community. Situated on the Tred Avon River, Easton is home to the Waterfowl Festival, an annual festival held each October drawing nature lovers and artists from around the world. Plein Air Easton is another annual festival held each July that has been called the largest and most prestigious juried painting competition in the US.
In addition to art, Easton has a reputation as one of the best dining destinations in the Mid-Atlantic region. Scossa Restaurant & Lounge on Washington Street serves breakfast, brunch, dinner, and Italian specialties as well as alcoholic beverages. Another popular gathering spot in Easton is Hunters Tavern, inside the historic Tidewater Inn on Dover Street. Here, you can taste some of the most delicious flavors of the Eastern Shore, such as the restaurant's renowned snapping turtle soup.
North East
The charming waterfront village of North East, at the head of the North East River in Cecil County, is home to just over 4,000 residents and has long been known as a destination for boaters. In 2025, the town announced an investment in Main Street to enhance its aesthetics and accessibility and increase tourism. The expected investment from the town is projected to go towards clearer signage and better landscaping, as well as improving family amenities in the North East Community Park.
Walking down Main Street North East provides an experience for all of the senses, from the beauty of the jewelry at unique independent shops like Silver and Sassy to delectable smells from the sweets and treats at Chesapeake Bay Coffee Company. Hungry visitors as well as townsfolk know to stop by Woody's for the best seafood and crabs in town.
Brunswick
The Frederick County community of Brunswick, population just over 7,700, is another designated Main Street Maryland town. As of 2025, the town has secured grants for Main Street businesses to improve the health and welfare of older commercial properties with fewer than 15 employees. The community hopes to grow and enhance the Main Street experience through projects such as this.
There are many shops whose goods can be perused in the downtown Brunswick area, such as Antiques N'Ole Stuff on Potomac Street and Lockhouse Gallery, featuring all types of art, also on Potomac Street. The Potomac Street Grill serves a menu of American and Mediterranean fusion. Boxcar Burgers on Maple Avenue features simple foods, as well as sweet treats, with ice cream locally sourced from Great Fall Ice Cream in Gaithersburg.
Check Out These Main Streets in Maryland
From the mountains of towns such as Oakland and Cumberland, to the Eastern Shore communities like North East and Easton, Maryland is full of diversity, history, culture, and fun. These towns represent the best of Maryland's quaint, charming downtown areas. Whether you are looking for a new place to explore during your next sojourn or are thinking of moving to a new town, these 11 Maryland towns and their main streets beckon you with a welcoming atmosphere.
