10 Maryland Towns With Unforgettable Main Streets

When traveling to a new city or town, the best opportunities to discover it lie in the downtown district. These social hubs harbor major historical landmarks, commercial institutions, and cultural venues, serving as crucial gathering places for newcomers. While Maryland is known for big cities like Baltimore, it has a long list of beautiful little towns that embody the true heart and soul of the Old Line State.

Some of these boast well-preserved historic downtown districts and revitalized Main Streets, where history, culture, and commerce harmoniously coexist to offer visitors a feel for local character. From the artsy avenues of Havre de Grace to the rustic streets of Chestertown, discover Maryland towns with unforgettable Main Streets.

Sykesville

Situated a short drive from the bustling scene of Baltimore and Washington, DC, this little town houses a compact yet site-rich downtown. At the center of the urban square is the Sykesville Historic District, which provides a glimpse into the past with its collection of Victorian structures, highlighted by the Historic Town House Marker from 1883. The busy neighborhood hosts the weekly Downtown Sykesville Farmers Market, where guests can indulge in local flavors while shopping for fresh produce, baked goods, and artisan goods.

Several eateries and watering holes provide opportunities to get together with the residents and other tourists. If you relish a hearty meal, you can pop into EW Beck's Restaurant & Pub for warm nachos and burgers or Patapsco Distilling Company for a craft spirit.

Chestertown

Chestertown is one of the oldest towns in Maryland, boasting a heritage dating back to the start of the 19th century. It has a rustic downtown area boasting an impressive blend of history and culture, marked by vintage structures and art centers. Walking down the Main Street Chestertown district, you will come across the Garfield Center for the Arts, known for hosting a lively lineup of musical and theatrical presentations. The MassoniArt Gallery displays a colorful collection of exhibits by artists accumulated over decades.

Meanwhile, visitors can learn a lot about Chestertown's dynamic history at the Historic Society of Kent County by perusing artifacts, archives, and documents. Main Street Chestertown comes alive during the annual Chestertown Tea Party Festival, which brings a weekend of fun activities for all ages.

Havre De Grace

Havre de Grace is a picturesque town in Harford County, known for its unparalleled waterfront views, a picturesque promenade, and interesting museums. Its downtown region showcases a rich blend of history, culture, and entertainment, inviting first-timers to learn about its heritage at the Havre de Grace Maritime Museum. Meanwhile, the Havre de Grace Promenade presents some of the best views in the town. This quiet walkway overlooks the dramatic intersection between the Susquehanna River and Chesapeake Bay.

A thriving craft brewery scene in Havre de Grace promises first-timers exciting tasting experiences at Market Street Brewery, where you can enjoy a refreshing pint of beer. Finally, the Friends-Concord Point Lighthouse decorates the downtown skyline with its 36-foot facade, serving as a stark reminder of its nautical history.

Cumberland

This historic town in Western Maryland entices visitors with its blend of cultural venues, historic structures, and dining spots, spread across its pedestrian-friendly downtown district. Baltimore Street forms the heart of the town square and hosts various events, shops, stores, and businesses. The Allegany Arts Council welcomes visitors to check out intricate creations by local artisans and attend walk-ins and other events. Those who enjoy theatre can catch engaging musicals and dramas at the Cumberland Theatre by professionals.

Historians will have a blast exploring the town's past at the Gordon-Roberts House, which still maintains a variety of Victorian furnishings. Whenever you need to eat, be sure to stop by Ristorante Ottaviani and enjoy sumptuous and authentic Italian cuisine, including cannoli and pasta bolognese.

Berlin

Berlin is one of Maryland's towns with unforgettable Main Streets, owing to its dynamic Berlin Commercial District. Its vibrant Main Street is lined with at least 60 galleries, restaurants, boutiques, and other businesses, resulting in a popular gathering hub. You can start exploring at Berlin Main Street & Maryland Welcome Center, which provides tourists with in-depth information about the best things to do and places to go around the neighborhood. This includes getting a feel for local history at the Calvin B. Taylor House.

Also, foodie can make the most of dining and wining opportunities at BourAgave Bourbon & Tequila Joint, which tantalizes palates with a unique mix of Spanish flavors and Southern-style cooking. Later, you can wash down the meal with refreshing craft beers at Burey Oak Taproom & Brewing Company.

Kensington

Kensington is a quaint borough in Montgomery County, reputed for its Victorian homes and a lively downtown landscape. Main Street, popularly known as Antique Row, features a collection of antique shops, restaurants, boutiques, and galleries. You can sort through an impressive library of vintage treasures and furnishings at Design Emporium and Antiques. The Kensington Arts Theatre connects the community with the arts by hosting a lineup of dramas, musicals, and other live performances.

The Kensington Farmers Market breathes life into the downtown region as local growers and crafters line their assorted merchandise along Howard Avenue, luring guests with a casual shopping experience. If you visit with kids, remember to take them to the Noyes Library for Young Children.

New Market

Nicknamed "Antiques Capital of Maryland," New Market is a historic town in Frederick County with an enduring heritage that plays out across its historic district. Exploring the neighborhood reveals a colorful cluster of vintage homes and antique stores. Souvenir collectors are in for a fun experience hunting for unique treasures at Robert Esterly Antiques or Fleshman's Antiques. While on Main Street in New Market, consider passing by the Village Potter to check out intimate jewelry and pottery creations by local artisans.

When tired from all the walking around downtown New Market, feel free to take a rest and revel in the serene scene of Community Park.

Cambridge

Cambridge boasts a rejuvenated downtown district set along the scenic bank of the Choptank River. It has a unique maritime heritage, which newcomers can learn more about inside the Choptank River Lighthouse, which stands out for its screwpile style design. While there, take advantage of the unrivaled water views for a photo opportunity. There is more to see inside the Richardson Maritime Museum, whose exhibits document over three centuries of regional nautical history.

The Dorchester Center for the Arts is the perfect stop for art enthusiasts. The venue brings locals and visitors together for workshops, classes, gallery shows, and performances. One of the best times to explore downtown Cambridge is during the annual Groove City Culture Fest, as the corridor erupts into a vibrant celebration of music and culture.

Crisfield

Crisfield is a small waterfront community on Maryland's Eastern Shore with a scenic downtown corridor bordering the shiny waters of Chesapeake Bay. Its walkable Main Street is home to Tangier Island Cruises, which treats guests to a fun tour on the water, exploring the surrounding areas. While strolling down the main thoroughfare, you will bump into the Bay Gift Vault, which sells a lovely collection of handmade jewelry, decor items, t-shirts, and other accessories.

The Crisfield Arts and Entertainment District offers proof of the region's thriving arts community. Visitors have a blast mingling with craftsmen, artists, musicians, and performers in an upbeat atmosphere. Lastly, those interested in Crisfield's history can find dependable resources at the Crisfield Heritage Foundation.

Ocean City

This popular holiday town on the Atlantic Ocean charms travelers with its sunny weather, white sands, and sprawling waters. Its main street, Atlantic Avenue, is the heart and soul of the community and compels newcomers and residents to gather along the lively corridor of Ocean City Boardwalk. The location has everything from amusement parks and souvenir shops to restaurants. You can get adventurous with a thrill ride at Trimper Rides of Ocean City, featuring heart-stopping roller coasters.

Meanwhile, you can learn some enduring local history at the Ocean City Life-Saving Museum, whose collection of artifacts highlights the culture of life saving on the Eastern Shore. Finally, stop by Ripley's Believe It or Not to browse a display of oddities.

Some of the best experiences in Maryland take you from the busy metro areas to the quiet rural towns. Despite their low-key setting and underwhelming reputation, some have vibrant downtown areas with buzzing thoroughfares that promise a rich mix of experiences. Whether a foodie looking to savor sumptuous seafood in Ocean City or a historian planning to explore the past eras in New Market, the best Maryland towns with unforgettable Main Streets deliver a wholesome traveler experience.