8 Most Charming Town Squares In Maryland

Maryland is a Mid-Atlantic state, renowned for its extensive coastline along the Atlantic Ocean and the Chesapeake Bay, the largest estuary in the world. It also has a rich history that has been preserved in the seafaring communities that call the state home. These eight towns have charming town square areas, each reflecting the spirit of the state, while also adding its own flair.

The downtown sections are arguably the best destinations for getting to know the community's fabric, and these eight are no exception. These districts are where the locals go to shop, dine, and catch up on local news. A distinctive feature of each is the merging of history and modern amenities, which combine to make memorable destinations, perfect for a getaway.

Annapolis

Annapolis is renowned for being the home of the United States Naval Academy and its historic district, which features elegant 18th-century brick homes. It also has a charming town square area, centered around Main Street, with compact streets and unique finds. Little has changed since its 17th-century inception, except that the original structures now house modern restaurants and shops at the Annapolis Town Center.

You can also head up the hill to State Circle for a glimpse at the opulent Maryland State House. After snapping photos and basking in the capital's elegance, head to Maryland Avenue for more shops and restaurants like the Royal Blue. Downtown Annapolis is unbeatable for its collection of historic structures and shopping opportunities, which add to its distinctive charm.

Berlin

Downtown Berlin is a thriving district with a vibrant art and culinary scene. The state-designated Arts and Entertainment District features public murals, including the Dr. Reverend Charles Albert Tindley mural and the Pollinator Way interactive mural. Dining options include the local favorite Blacksmith Restaurant, which features a chef-inspired menu and farm-to-table fare.

Berlin's town square district is just fun to walk around, and there seems to be something fun to do in every corner. An exciting way to discover the area is by taking the 1.5-mile Haunted Berlin Ghost Walk. The guided stroll passes by the enchanting Atlantic Hotel and other structures rumored to be haunted by ghosts. The area also has a distinctive community vibe, similar to the peak era of Americana downtowns.

Havre de Grace

Historic Havre de Grace boasts a fantastic, walkable downtown district featuring beautiful structures and a vibrant atmosphere. The charming district is a shopper's paradise, from boutiques to antiques at retailers such as Blast From the Past and Breezy Bay Boutique. The district also boasts a thriving artistic scene, as evidenced by the numerous public murals and galleries downtown.

The Cultural Center at the Opera House is a historic venue that should not be missed. The historic theater serves as a cultural hub, hosting live plays, events, and art exhibitions that contribute to the region's charm. First Fridays is an ideal time to visit downtown, when vendors and live music acts take to the streets for a fun and community-oriented event.

Easton

Easton's town square area is a Main Street Maryland community, boasting eclectic art galleries, award-winning restaurants, and small-town charm. Shopping is a favorite pastime here, especially as autumn kicks off with the annual Fall Kickoff Weekend. Unique shops include The Bazaar on Federal Street, along with a host of other boutiques.

Gourmands will enjoy the eclectic dining scene downtown, with numerous offerings and distinctive pairings. Dinner options include Bas Rouge, a contemporary European restaurant, and Genesis Restorante, offering a pleasant combination of Mexican and Italian fare. Easton's downtown is modern while still retaining its original charm, making it one of the best districts in the state.

St. Michaels

Beautiful St. Michaels has extensive shopping and dining options in its quaint downtown district. The waterfront area features a blend of modern retailers and antique shops, including Antiques on Talbot. The walkable district offers a wide variety of dining choices, such as Bistro St Michaels and Corah's Corner.

The bistro is an excellent choice for a light lunch while exploring downtown. Corah's is ideal for a casual dinner with a lively atmosphere. No trip is complete without stopping at the Chesapeake Maritime Museum that interprets local and regional maritime history, an intergral part of the community's fabric.

Cumberland

Cumberland's town square section is a historical area with a three-block pedestrian mall, diverse restaurants, and a friendly atmosphere. This region is known as Maryland's mountain region, and the classic brick structures and church steeples reflect the region's ambience. Download the Cumberland Historic Walking Tour map to discover landmarks like the Allegany Museum.

The remodeled 1930s building interprets the region's heritage through exhibits and tours. Another landmark is the Embassy Theatre, opened in 1931 and one of the town's most notable Art Deco buildings. There are many other structures to see and, if you want to immerse yourself in Cumberland's history, book a room at the 1917 Fort Cumberland Hotel, now known as the Cumberland Hotel.

Sykesville

Sykesville is a charming area with colorful buildings and a friendly atmosphere that Budge Travel called " Coolest Small Town in America" in 2016. As you stroll past the distinctive buildings, look out for boutiques like CharlieJoe's Clothing and A Likely Story Bookstore, both of which are popular for residents and visitors alike. Along the way, you will discover murals that reflect the community's artistry and principles, such as the community mural that connects artists from around the world.

All that walking works up an appetite, and Sykesville has that covered in spades. Main Street Bistro is an ideal lunch spot, or you can opt for Patapsco Distillery for fun food and libations. There is much more to see and do in this friendly town with an artistic and cultural twist, and it is one of the coolest areas in Maryland.

Oakland

Downtown Oakland is a pedestrian-friendly area in the mountainous region of Maryland. The small-town atmosphere and live events like the upcoming Autumn Glory festival add to the charm. It is also a fascinating sight in the winter when white lights adorn almost every storefront and downtown building. Booking a room at the Suites at Silver Tree will keep you in the heart of the district while also providing elegant rooms that match downtown's characteristics.

The Farmer's Market at the Mountain Fresh Pavilion provides an excellent opportunity to meet the friendly community. After the market, stop at Our Town Theatre, which also supports the community. The small-town arts scene is irresistible and captures the district's soul like perhaps no other venue. This is one of the most charming town square districts in the region, especially during one of the annual festivals or events, and should top every traveler's destination list.

Although this is a different vibe than the social hubs of traditional town squares, these eight are the most charming in Maryland. Whether seeking a tranquil retreat or an electric night in town, these districts fit the bill. Towns like Annapolis are saturated in Naval traditions combined with modern shops, while St. Michaels is full of historic charm, each offering vibrant sights and sounds.

The downtown areas also offer a unique opportunity to connect with the community and stay informed about the latest local news. Grab a cup of coffee and hit the pavement for window shopping, and maybe take in a live show at a park or live theater. The community, preserved sites, and eclectic dining opportunities make these town square areas the best in the Old Line State.