9 Most Charming Town Squares In Maryland
The town square still runs the show in a lot of Maryland. Denton wraps its courthouse green in canning-era storefronts that have watched circuses and ballgames pass through. Havre de Grace turned a waterfront alley beside its square into a gallery of three dozen murals. Nine Maryland squares still earn their keep as the center of town.
Annapolis
Sticking into the tidal estuary of the Severn River, Annapolis, Maryland, is home to both the state capitol and the United States Naval Academy. The Statehouse grounds are actually a circular green at the center of town. Red brick sidewalks lead up to the Maryland State House, situated on the west side of the park. The center of state government is open to tours daily, and the historic State House Cannon stands out front. Here stands Maryland's oldest public building, the Old Treasury Building, constructed between 1735 and 1737.
For a place to stay, the Historic Inns of Annapolis sit just across State Street from the square. These inns combine the historic Maryland Inn, the Governor Calvert House, and the Robert Johnson House. A block from the square is the campus of St. John's College, home to the Liberty Bell Replica. The Department of the Treasury cast the replica bell in 1950 and presented it to Maryland. If you would rather experience Maryland's maritime history, head away from the square toward the Annapolis City Docks. Here, Annapolis Tours By Watermark offers scenic boat tours. Options include trips past the Naval Academy, sightseeing on the Severn River and Spa Creek, and the Thomas Point Lighthouse and Bay Lighthouses cruises.
Hagerstown
Continue heading west, and you will find Hagerstown in the Great Appalachian Valley. The historic Old National Pike or National Road, the first Congressionally funded roadway, runs through town. George Washington and Thomas Jefferson both believed the roadway provided an essential link to the western United States.
The Hagerstown Public Square is located at the intersection of Washington and Potomac Streets in the downtown center. Mornings here often start with a cup of locally roasted coffee. Cannon Coffee faces the square, one of two locations of the independent shop founded by a hometown couple. The shop features coffee drinks and seasonal specialties. At the opposite corner of the square stands Gardenbelle Shop, a boutique featuring natural-fiber clothing. The store specializes in clothing made from certified organic fibers, hand-sourced upcycled fabrics, and vintage pieces. Afterward, you might want to catch a show just off the square at the Maryland Theatre. Built in 1915, the historic theatre began life as a vaudeville house. Today, the 1,293-seat theatre hosts private events, comedians, concerts, and the Maryland Symphony Orchestra.
Cumberland
Situated in the Allegheny Mountains, Cumberland, Maryland, serves as the Allegany County Seat. At the center of the visitor district is Canal Place Historic Park. The park sits within the visitor district alongside the Western Maryland Scenic Railway. The historic rolling stock includes two steam engines. Excursions on the line include dinner trains into the Allegheny Mountains and murder mystery performances. The park also marks the beginning of the Chesapeake & Ohio Canal Towpath. The former canal has been converted into a 184-mile, multi-use trail for biking, running, and walking. Along the path, you can also view the Historic Canal Boat Replica, just south of the park.
Opposite the square is the Allegany Museum. The Art Deco and Neoclassical Building, erected in 1932, showcases the museum's 50,000-piece collection. The museum celebrates the industrial past of the Allegany Region and Native American history throughout the area. A block to the north, you'll find the pedestrian-only Baltimore Street, the historic shopping district of the city. Grab a bite to eat here at local restaurants like the City Lights American Grill. The bistro-style menu offers seafood, steak, and pasta. City Lights also has homemade cheesecake and pies. If you'd rather have a scoop of ice cream, head down the street to Queen City Creamery Scoop Shop for a cone, shake, or ice cream cake.
Easton
Easton has gained a reputation for its walkable downtown and eclectic shops. Thompson Park sits at the center of all the action. Book lovers, for instance, will find three stores within a block of the square. Flying Cloud Books has a curated selection of new releases, Vintage Books offers rare and out-of-print titles, and Crackerjacks is stocked with a variety of children's books. There are plenty of other shops too. The Marc|Randall boutique, just across the street from Thompson Park, features women's clothing designs from around the world.
Sitting across from Thompson Park, the Prager Family Center for the Arts presents performances and educational events at the Ebenezer Theater. The theater also hosts regular movie nights highlighting vintage films. Across the street is the Talbot Historical Society. Six buildings comprise the organization's campus, including the Mary Jenkins House. The house dates to at least 1783 and is believed to be the oldest frame house in Easton. The society also hosts exhibits on local history.
Havre de Grace
Havre de Grace sits at the mouth of the Susquehanna River and has an active waterfront. Here you will find marine services, such as boat slip rentals and boat repair, from local businesses like Tidewater Marina. If you don't have any maritime experience, you can learn to sail at the BaySail School of Sailing. The school offers introductory sailing classes, private training, and American Sailing Association certification.
Graw Alley, a public green space, connects the river waterfront to Market Street. Founded in 2023, the park now features 36 building-sized murals. The Graw Alley Art Party Series hosts events on the first Friday of each month from May until October, featuring music and art exhibitions. You can keep the party going a few doors down, at the Market Street Brewery, where river views come with the brewery's craft beer on tap. It's all just a short walk to the main downtown district on North Washington Street.
Denton
Denton sits on a hill above the Choptank River as the seat of Caroline County. At its center is the Courthouse Green, where the county courthouse still presides over a square ringed by colonial revival homes and storefronts built during the area's canning boom between 1895 and 1919. The town dates to 1781, and the Green has served as the setting for balls, circuses, baseball games, and military parades. Every August, Caroline Summerfest takes over the streets around the courthouse.
The blocks around the Green hold most of the town's attractions within an easy walk. The Museum of Rural Life covers Eastern Shore farm and town history, and nearby, the Fiber Arts Center of the Eastern Shore and the Foundry give area artists a place to show their work. Shore Gourmet Market at the Chesapeake Culinary Center offers a food stop along the way, and independent shops and restaurants line the surrounding streets.
Chestertown
Chestertown's downtown sits between the Washington College campus and the Chester River. Fountain Park, at the center of town, hosts events like Paint The Town, where artists have two hours to draw before their work is judged and displayed in the park. Around the park are local shops. Check out Walnut & Wool, a women's clothing store, or Houston's Dockside Emporium, which features gifts, books, and knick-knacks.
Extending from the park along High Street is the weekly Chestertown Farmer's Market. The community tradition started with local farmers bringing their goods to the center of town on horse-drawn wagons. Today, local food vendors and artisans gather on Saturday mornings year-round. In addition to farm-fresh foods, vendors sell gifts and merchandise produced from local animals. A few blocks away, the Lawrence Wetlands Preserve includes 8.5 acres of open space with a short walk through the marshes and wetlands. There is also a connection to the Wayne Gilchrest Trail, an adapted rail trail that runs from downtown through the Washington College campus.
Leonardtown
Leonardtown spreads across the waterfront of Breton Bay, an inlet at the mouth of the Potomac River. Leonardtown Square sits at the center of the town's historic district, surrounded by Washington Street and Fenwick Street. The Upper Square includes the War Memorials Garden, which honors the local men who died during World War I. Throughout the warmer months, the square hosts numerous concerts, such as Swing into Spring and the Summer Concert Series.
The square is the perfect place to start your morning off. Grab a coffee from SOCIAL Coffeehouse & Cocktail Bar, a local roaster overlooking the square. The restaurant offers brunch and dinner, and is open late for drinks, too. Across the square, you can grab a sweet treat at The Salted Scoop. The shop serves a rotating selection of ice cream flavors and homemade cones. Also facing the square is New View FiberWorks, a women's cooperative that sells handmade knitted items such as shawls and scarves. The store also stocks handmade soaps, pottery, and jewelry made by local artisans. And if you need a place to stay, just off the square, you will find The Inn at Leonardtown, a boutique hotel.
Centreville
Centreville sits at the head of the Corsica River as the seat of Queen Anne's County on the Eastern Shore. Its center is the Courthouse Green, laid out in a colonial town-square style, with a statue of the county's namesake, Queen Anne, standing in the middle. The green's western end holds the Queen Anne's County Historic Courthouse, a white-brick Federal building completed in 1792 that served as Maryland's oldest courthouse in continuous use until a new circuit court opened in 2019. The statue was unveiled in 1977 by Princess Anne and is said to be the only one of Queen Anne outside England. The square hosts Centreville Day, Maryland Crafted/DrinkMaryland events, and a Sunday farmers' market.
A short walk from the square, the Queen Anne's County Historical Society keeps two period houses open for tours: Tucker House, built in the 1790s on the second lot ever sold in town, and Wright's Chance, an 18th-century farmhouse with original wood paneling. For a drink, Bull and Goat Brewery and Old Courthouse Distilling share a downtown space, and nearby, Commerce Street Creamery serves homemade ice cream and bakery treats.
Maryland's Best Squares Are More Than Pretty Parks
Public squares serve their communities as third spaces where people gather, shop, and support small businesses. In these Maryland towns, the square still does that work: Chestertown's vendors set up on Saturday mornings where farmers once arrived by horse-drawn wagon, and in Centreville, a statue said to be the only one of Queen Anne outside England stands at the center of the green.
