These 11 Towns in Maryland Have Bustling Main Streets
Main Street is the lifeblood of any town or city, and Maryland offers a long list of vibrant communities brimming with character. Beyond the crowded streets of Baltimore, the Old Line State houses beautiful small towns with high-spirited downtown districts, where history, community, and commerce collide in a fun, social atmosphere. They present the perfect starting point for exploring the area, with a chance to discover historical landmarks, browse local businesses, and indulge in homegrown cuisine.
Additionally, the pedestrian-friendly configuration allows newcomers to move conveniently from one point of interest to another. Whether you want to shop for antiques along the rustic streets of Kensington or connect with the arts in Chestertown's old town district, these towns in Maryland have bustling Main Streets.
Cumberland
This beautiful municipality in western Maryland harbors a lively downtown district that seamlessly blends cultural venues, historical sites, shopping outlets, and dining joints. The pedestrian-friendly main street is home to the Cumberland Pedestrian Mall, a three-block establishment with a mix of shops, boutiques, eateries, and galleries. Stop by the Queen City Creamery Scoop Shop for a delicious ice cream or milkshake to calm your sweet cravings.
The Allegany Museum is a short walk off the main thoroughfare and invites newcomers to explore various artifacts about the town's history inside a Neo-Classical Revival building. Before leaving the neighborhood, spare a few hours to watch a live presentation at the Cumberland Theatre.
Cambridge
This community on the Choptank River is steeped in maritime heritage and colonial history. Its revitalized downtown district boasts many restaurants, shops, old homes, and art centers, overlooking the calm river waters. The Dorchester Center for the Arts is a significant draw along High Street, offering guests visual and performance art opportunities through exhibitions and events. Not far from this spot, you will come across the Richardson Maritime Museum, which is dedicated to chronicling centuries of the region's maritime history.
The Choptank River Lighthouse is perfectly visible from downtown Cambridge and stands out for its classic screwpile design. Besides being a postcard-worthy landmark, it reminds of the town's enduring heritage since it was erected in the 19th century.
Berlin
Berlin is known for its always busy Berlin Commercial District, hosting an eclectic blend of restaurants, galleries, boutiques, antique shops, and other local businesses. The Berlin Main Street and Maryland Welcome Center offer first-timers a proper reception. It has all the information to fashion a perfect itinerary along the main avenue. This includes visiting the Calvin B. Taylor House to check out original furnishings and artifacts from the late 19th century.
Main Street also hosts the weekly Berlin Farmers Market, where guests can shop for unique products from over 50 local vendors. Lastly, don't forget to sample the delicious flavors at 410 Social Eatery & Barroom, which features tasty burgers and sandwiches.
Crisfield
Crisfield has a picturesque waterfront downtown district that spoils guests with unparalleled vistas of the Chesapeake Bay. The Eastern Shore town allows you to access the waters for a fun sail through the Tangier Island Cruises. Booking the trip will enable you to explore the downtown scenery from the water en route to the neighboring Tangier Island.
Meanwhile, the Crisfield Arts and Entertainment District is a delightful cultural hub with a vibrant community of creatives. It has a nice spot to watch exhibitions, listen to musicians, and watch street performers perfecting their craft. If you want a souvenir for your time in Crisfield, you can pass by The Bay Gift Vault and sort through its collection of accessories, decor items, jewelry, and more.
New Market
New Market is a historic municipality in Frederick County known for its wealth of antique shops. Its charming historic district hosts a mix of vintage homes and old buildings hinting at its enduring heritage. The Henkel House is a prominent landmark along the corridor and brings back memories of New Market in the 19th century. It was initially constructed in the early 1800s and played a role during the Civil War. Antique collectors are spoilt for choice in downtown New Market, with a chance to find unique treasures at Fleshman's Antiques.
Alternatively, The Village Potter sells beautiful ceramics that improve your home decor, jewelry, pottery, tableware, and other handcrafts. Also, you can find a nice green space to relax and breathe fresh air at the New Market Community Park.
Ocean City
Ocean City is one of the best small towns in Maryland, not just for its sunny weather and coastal scenery but also because of its lively downtown corridor. Main Street harbors the city's lifeblood, and tourists gather here to enjoy the stunning water vistas during lazy walks along the Ocean City Boardwalk. This adorable promenade hosts a variety of businesses, amusement parks, and more, resulting in an upbeat social setting. Thrill seekers can ride a roller coaster at Trimper Rides of Ocean City to enjoy themselves.
Elsewhere, Ripley's Believe It or Not! interests tourists with quirky exhibits and oddities that will have them questioning their thought process. Lastly, remember to explore the town's coastal heritage at the Ocean City Life-Saving Museum.
Havre de Grace
Havre de Grace's downtown region overlooks the beautiful confluence of the Chesapeake Bay and the Susquehanna River. Its pedestrian-friendly atmosphere allows visitors to explore local attractions comfortably. The Havre de Grace Promenade is one of the most popular escapes in the area and spoils newcomers with unprecedented views of the water. Meanwhile, the Havre de Grace Maritime Museum showcases a catalog of rare artifacts documenting the region's nautical history.
From downtown, you can't miss the imposing Friends-Concord Point Lighthouse, a stunning reminder of past maritime expeditions. Additionally, use the opportunity to taste great-tasting craft beers at Market Street Brewery.
Sykesville
Sykesville offers visitors from nearby D.C. and Baltimore a less crowded downtown atmosphere without diminishing the vibrancy. The town square harbors the Sykesville Historic District, where a collection of Victorian structures reminds newcomers of the town's long heritage. This includes The Town House, which was constructed for an Irish immigrant and his wife in the 1880s. Every Sunday from May through October, the Downtown Sykesville Farmers Market livens up the main street as dozens of farmers and vendors sell their baked goods, farm produce, and craft items.
Meanwhile, numerous pubs and diners in the area invite tourists to hang out and catch up during their free time. If you want something to eat, pop into EW Beck's Restaurant & Pub for delicious eats, draft beer, and creative cocktails.
Kensington
Kensington is a charming village with a glowing heritage that shows throughout its Victorian downtown region. The main thoroughfare is named Antique Row and is lined with everything from boutiques and galleries to restaurants and souvenir shops. Design Emporium and Antiques is where visitors go to seek gift items to bring home. Elsewhere, art enthusiasts keep busy watching live presentations at the Kensington Arts Theatre. This popular hub hosts a lineup of musicals, dramas, and plays for the public's amusement.
Additionally, shoppers can find exciting opportunities during the weekly Kensington Farmers' Market. This welcoming gathering of area vendors and crafters offers an array of products and a chance to learn about local culture from personal interactions.
Chestertown
Chestertown is steeped in history, and you only need to stroll through its downtown district to notice this. The rustic corridor is dotted with Victorian storefronts and old buildings housing restaurants, galleries, museums, and local businesses. The Garfield Center for the Arts is a popular location along Main Street and serves as the regional hub for watching diverse theatrical performances. Downtown also presents visual art lovers with plenty of areas to browse local creations, including Chestertown RiverArts.
If you are interested in the community's longstanding heritage, the Historical Society of Kent County has resourceful information about it. Finally, one of the best times to experience Main Street Chestertown is during the Chestertown Tea Party Festival.
Leonardtown
This St. Mary's County community is known for its vibrant Arts and Entertainment District, where a cluster of eateries, galleries, museums, shops, and boutiques culminate in a beehive of activities. The corridor seamlessly mixed the new with the old, and historians take a glimpse of the past years at the Old Jail Museum. This old sheriff's office was constructed in the 1870s. Shopaholics can find over 90 shops at Shepherd's Old Field Market for an immersive retail therapy session.
Also, Leonardtown's charming waterfront scenery lures vacationers with soothing moments on the quiet grounds of Leonardtown Wharf Park. The space is ideal for lazy picnics while soaking up sweeping panoramas of the Potomac River.
These bustling towns in Maryland demonstrate that you don't have to restrict yourself to the big cities to experience the state's urban flair in the United States. Their attraction-rich downtown areas and busy thoroughfares allow you to design a day-long itinerary around various points of interest in the small neighborhood. Whether you plan to enjoy the lively arts landscape in Cambridge or delve into Havre de Grace's rich maritime heritage, these lovely destinations offer an authentic feel of the Old Line State.
