8 Best Downtowns In Maryland

Downtowns are the heart and soul of any town or city! They are where the arts, history, culture, and entertainment collide, making them crucial stops for tourists. With more than 30 Main Street communities, the Old Line State has a fair share of exciting downtown areas where newcomers can get an authentic Maryland experience. But unlike the bustling cities with crowded streets, smaller towns are more comfortable to explore due to their walkability and easygoing pace.

Whether you like to window shop on foot, dine at trendy restaurants, hunt for vintage treasures, or examine the unique architecture of historic buildings, there is no limit to possibilities in the state's charming small towns. Between this rustic charm of New Market and the artsy streets of Havre de Grace, here are some of the best downtowns in Maryland.

Crisfield

This Eastern Shore community of Somerset County might be small but big on personality. It has a beautiful downtown area overlooking the Chesapeake Bay and offers ready access to the waterfront. Tangier Island Cruises, along Main Street, takes guests on laid-back tours that explore the town from the water. Crisfield has a thriving community of artists, craftsmen, musicians, and writers cramped up at the Crisfield Arts and Entertainment District. This vibrant hub welcomes newcomers to browse local art in three galleries, watch street performers, and buy sophisticated crafts for an engrossing cultural experience.

The Smith Island Baking Company indulges your sweet tooth with an assortment of delicious snacks and confectionaries. However, the highlight is getting to taste Maryland's official dessert, the 10-layered Smith Island cake draped in chocolate icing.

Cumberland

Cumberland is known for its impressive blend of the new and the old, and this merging of generations plays out harmoniously in its adorable downtown. On the one hand, tourists can travel back in time with a tour of the 19th-century Gordon-Roberts House. The mansion was built by a prominent attorney, Mr. Gordon, in 1867 and features period furnishings and artifacts reminiscent of Victorian life. George Washington's Headquarters takes visitors further back to the mid-1700s and preserves a historic log cabin where President Washington once sought refuge.

On the other hand, the town showcases its more contemporary side at the Cumberland Theatre. This lovely venue is the sole professional theater in Western Maryland and hosts an array of live performances, including dramas, music, and comedies.

Havre De Grace

Havre de Grace boasts a bustling downtown area with an eclectic mix of restaurants, galleries, museums, bakeries, breweries, and other local businesses. The Havre de Grace Maritime Museum collects and preserves a variety of historical artifacts, shedding light on the local crabbing and fishing history. Meanwhile, the Havre de Grace Decoy Museum exhibits a quirky collection of duck decoys and fine art models that pay tribute to the art of decoy making and the tradition of waterfowling in the region.

Given its location at the junction of the Chesapeake Bay and Susquehanna River, Havre de Grace delivers a genuine waterfront experience when walking along the Havre de Grace Promenade. It is a lovely spot to watch the birds fly over the water and the Friends-Concord Lighthouse, which rises 36 feet into the air and is a prominent town landmark dating back to 1827.

Cambridge

Cambridge's revitalized downtown lies along the banks of the Choptank River and features a cluster of restaurants, galleries, shops, and other local businesses. It hosts vital cultural spots like the Harriet Tubman Museum, which honors the legacy of Harriet Tubman with a brief video footage. Its exhibits also highlight different historical moments in American history, such as the Civil War and the Underground Railway. The Dorchester Center for the Arts is the local culture hub. It hosts changing exhibitions and galleries, as well as a performance hall to enrich the arts community on the Eastern Shore.

Several eateries in the neighborhood serve delicious flavors when you need something to eat. At the Blue Ruin, you can enjoy a seafood gumbo with a cocktail glass as live music from a piano plays. Downtown Cambridge also stages different events and festivals that add to its flavor, including the Groove City Jazz & Blues Fest.

Ocean City

Ocean City has one of the busiest downtowns in Maryland, thanks to a steady stream of tourists throughout the year. The 3-mile Ocean City Boardwalk is always a bee-hive of activities, with visitors flocking to the shops, craft stores, eateries, and entertainment spots lining the wooded promenade. Families always have a blast at Ripley's Believe It or Not! This whimsical museum has a selection of weird exhibits, ranging from strange animal skeletons to shrunken human heads.

Those who like to wine and dine can sample Maryland's seafood cuisine at Ropewalk Ocean City, which serves sumptuous crab cake sandwiches and shrimp dishes. Meanwhile, shopaholics enjoy an exceptional experience at Outlets Ocean City, home to a variety of designer stores and brand-name outlets like Adidas and Michael Kors.

Williamsport

Williamsport's history is built on welcoming visitors since its formative years, from fur traders to Native Indian tribes, thanks to its strategic location on the Potomac River. Today, you can visit the C & O Canal Historical Park for a lesson on how the 184.5-mile-long canal has been a lifeline for communities along the Potomac River over the years. The Canal Quarters shed more light on the functioning of the canal by exhibiting restored lock houses. These have been rehabilitated and furnished with period decor to allow interested visitors to spend the night.

Leonardtown

Leonardtown's Arts and Entertainment District packs a punch with multiple shops, restaurants, galleries, and museums squeezed into its 100 walkable areas. This gives the region an upbeat atmosphere, where guests can explore the community's past at the Old Jail Museum. Constructed in 1876, it is the country's oldest sheriff's office and depicts the lives of period prisoners in an old granite and brick structure. At North End Gallery, Leonardtown's arts community showcases its talent using a collection of jewelry, crafts, and sculptures by almost three dozen juried artists.

Leonardtown's waterfront location gives it a relaxed vibe. Visitors looking to take it easy can grab a bottle of wine at Port of Leonardtown Winery before finding a nice picnic spot at Leonardtown Wharf Park to revel in the scenery while sipping on tasty wines.

New Market

New Market is a welcoming little town with a well-preserved historic district that provides a perspective into its enduring history. The neighborhood is replete with vintage structures from the 19th century, such as the 1802 Henkel House, which gives it a unique and rustic charm. Furthermore, a series of antique stores give credence to New Market's moniker, "Antique Capital of the World." Souvenir lovers and antique collectors can pass by Fleshman's Antiques or Robert Esterly Antiques to comb through diverse vintage treasures worth investing in.

Art on Main is an excellent escape for those who appreciate the arts and nature. Set in the serene setting of Community Park, it features an intimate Butterfly Garden and elaborate sculptures created by artists like Parran Collery.

Downtowns are the best place to start exploring a new destination, particularly in the United States. They offer everything you may want to experience, from museums and art centers to restaurants and movie houses. The discussed destinations above have some of the best downtowns in Maryland, with a pedestrian-friendly atmosphere and a close cluster of attractions within walking distance of one another. Whether planning to shop in Ocean City or meet the locals in Cumberland, they are a great representation of the state's heritage and culture and promise first-timers a wholesome experience.