Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland.

These Towns in Maryland Have The Best Main Streets

Maryland, the state on the scenic banks of the famous Chesapeake Bay, is the birthplace of the national anthem in its vibrant city of Baltimore. This major historic trading port is also a baseball destination, where Francis Scott Key wrote "The Star-Spangled Banner" with views over the harbor six months before the War of 1812 ended. The Free State's towns boast historic downtowns with vibrant modern-day culture and scenic vestiges of the era along the main street that are worth a visit alone. Choose one of the waterfront towns with bayside trails, views, and summertime recreation galore. These main-street towns reminisce about the state's history for endless perusal through major historical sights, museums, and stunning architecture. Find attractions for tastes and ages through shopping and dining in the scenic embrace of historical sights and bay views, and join in regular festivals or any-day live music at outdoor concerts, art sights, and cultural strolls.


Downtown Berlin, Maryland. Image credit: Squelle, via Wikimedia Commons.

Berlin is a cool little town, just ten miles from Ocean City, with a picturesque main street. It is literally an eastern shore gem renowned for great jewelry, antiques, and other crafts. This charming small town of barely 5,000, chock full of pride, hosts an enchanting main thoroughfare of unique shops with attractive storefronts and entertainment for all. Join in regular live events like lawn concerts, quirky bathtub races, pageants, and street festivals every second Friday of each month.

Take joyous strolls among perusable hotspots to mingle, people-watch, or just relax amid sights on all sides. Check out the wealth of old buildings and stop by Burley Oak Brewing Company and the Maryland Wine Bar. Enjoy easy access to diverse outdoor activities and recreational pursuits, like concerts in the park, spectacular beaches nearby at Assateague State Park during the summertime, and Dr. Shred's Surf Adventures. This rural eastern Maryland gem, named as a variation on its old tavern, the Burleigh Inn, also hosts an annual fall peach festival.


View of the historic town of Chestertown, Maryland
View of the historic town of Chestertown, Maryland.

This town on the scenic banks of the Chester River boasts a lovely main street with an impressive historical edge in the collection of vintage buildings, including bed and breakfasts. Enjoy shopping and browsing through Chestertown's proud maritime sights from the Colonial era, with numerous museums and galleries, as well as events on the area's rich heritage. The lively thoroughfare is a popular destination for all seafaring fans on a stroll to the historically operating port, with docking and departing vessels of all kinds for lovely waterfront views.

Enjoy the scenery right from the aptly named High Street, descending all the way to the river, just a block over from the Marine, and another block to Wilmer Park. Check out the vibrant Fountain Park right in the middle of Main Street and the Riverfront Park near the water. There is also the autumn celebration of all things Harry Potter in the enchanting fall foliage on the Main and the magical Schooner Sultana, a beautiful 18th-century replica of a British Navy ship, harborside.


The J. Millard Tawes Historical Museum, a maritime museum in Crisfield, a town on the Chesapeake Bay.
The J. Millard Tawes Historical Museum, a maritime museum in Crisfield, a town on the Chesapeake Bay. Editorial credit: Linda Harms /

This characterful town in Somerset County is famous in its circle as the "Seafood Capital of the World," and a few restaurants around the country are named after Crisfield. Find a complementing Main Street steps away from the waterfront of Tangier Sound on the Chesapeake Bay, with popular must-stops and amazing seafood places you will reminisce about after. The Eastern Shore gem hosts spirited celebrations like the National Hard Crab Derby, the J. Millard Tawes Crab and Clam Bake, and the Scorchy Tawes Pro-Am Fishing Tournament. Take a boat tour around Smith and Tangier Islands or enjoy a stroll through Janes Island State Park with a picnic at beautiful marine and birdlife sights.

Having long recommended itself as a favorite, Crisfield avoided the economic combustion that other MD towns suffered from declining Chesapeake Bay industries. Visit the renowned small town for strolls along the vibrant streets cramped with arts, entertainment, and shopping opportunities in the community of visual and performing artists, writers, and other imaginative creatives and creators. Stop by the Smith Island Baking Co. for Smith Island Cake, the official state dessert, with chocolate icing in between ten layers of yellow cake.


Aerial view of Cumberland in fall.

This historic town played a strategic role during the Civil War and its aftermath. Today, the open-air pedestrian town center amid the Allegheny Mountains is an arts and shopping destination for one-of-a-kind country décor, a tea parlor, and woodworking, leather-making, pottery, and yarn studios. Discover Cumberland's railroad roots on a stroll along the lovely main street with a nostalgic feel in the air and vestiges like charming period buildings from that era.

This unique town in western Maryland hosts regular heritage events, and historical sights abound to discover its locomotive past amid some of the country's most striking architecture and equally beautiful nature. Spend a day along the Washington Street Historic District, with exquisitely preserved Gothic Revival architecture against the Appalachian backdrop, and stop by the Western Maryland Scenic Railroad Gift Shop for great souvenirs.

Ellicott City

The Ellicott City Historic District lies in the valleys of the Tiber and Patapsco rivers. Many of its buildings were constructed in the 1800s.
The Ellicott City Historic District lies in the valleys of the Tiber and Patapsco rivers. Many of its buildings were constructed in the 1800s. Editorial credit: Nicole Glass Photography /

Ellicott City is a small town with deep antiquity in heritage and architectural sights, markets, and shops selling all kinds of old crafts, collectibles, and vintage decor. It is among the most historic towns in the state; founded in 1772, it is home to the oldest surviving railway station in the US, now a museum made from blocks of locally quarried granite. The main street is a vibrant mix of trendy boutiques, bookshops, and local artisans.

Enjoy endless strolls amid over two hundred 18th and 19th-century buildings and stunning houses, like the Wayside Inn B&B, which once hosted General George Washington. Despite a recent flood, the mainstay is on fire with regular events like the Girl's Night Out in the Old Town. Visit anytime for the lively atmosphere and something fun for everyone, like plein air painting competitions, outdoor movie nights, ghost tours, concerts, and festivals. You can recharge at the plentiful specialty restaurants along the main street, including fine French and global fusion restaurants, breweries, and pubs.

Havre de Grace

The Lafayette Trail is a three-mile loop through the historic district of Havre de Grace. Editorial credit: Rosemarie Mosteller /

Havre de Grace is a waterside gem in Maryland, with St. John Street anchoring the shopping hub along the Susquehanna River. Discover the little town with a ton of personality on a stroll along its scenic main street with countless unique hotspots. Find unmatched waterfront views and shop for everything from toys and candy stores to quality leather goods and global fair-trade crafts.

Havre de Grace feels made for feel-good pursuits like relaxing strolls to peruse unique stores and delectable local cafes just steps away from the waterfront promenade. Vibrant events light up the streets in an atmospheric glow during the holidays and various festivals in town, like the festive First Friday block party. Stay for this weekly live music event with merchants every week from April through December in the downtown area closed to traffic.

Mount Airy

Main street in Mount Airy, Maryland.
Main street in Mount Airy, Maryland. Image credit: Acroterion via Wikimedia Commons.

The small town in central Maryland, some 45 minutes from Baltimore and Washington, is a sought-after breath of fresh air on a getaway from the city. Even the name emanates waves of scenic relaxation for strolls through the mountain's breeze and calm atmosphere to refresh and recharge. Explore Mount Airy on foot along the best main street, strewn with scenically backdropped hotspots, to feel part of the picture-perfect scenery.

The laidback atmosphere is complete with some of the state's best wineries in Maryland, making it the best place to relax like never before over some wine and views. Visit for some retail therapy along specialty boutiques in between art galleries down the main street. Enjoy good food, from outdoor bistros and cafés to local wineries just minutes from the downtown area, like Elk Run Vineyards or Linganore Winecellars, with wine tastings and live music.

New Market 

The New Market Historic District, New Market, Maryland, USA
The New Market Historic District, New Market, Maryland. Image credit: Acroterion, via Wikimedia Commons

This "Antiques Capital of Maryland" boasts a scenically historic main street for strolls no matter the season. New Market was established when the trading routes were connected through Baltimore and Frederick, with street sights still reminiscent of those times. Take a walk along the impressive collection of old buildings hosting antiquing shops and some of the most unique boutiques of your life.

The culture of the town is most vivid along the main thoroughfare, so find a café for some afternoon java to sip at the sights and absorb it all. Come for "A Day in New Market" in May or "Christmas in New Market" in December, its two state-famous annual festivals. Concentrated along the main street, you will feel part of the lifestyle highlighted in the 18th and 19th centuries in the New Market area. The scenically charged main street with restaurants and a few night spots recharges you with energy for another day of sightseeing and scoping out the town further, dotted with charms all around.

St. Michaels

The Chesapeake Bay Maritime Museum is located in St. Michaels, Marylan
The Chesapeake Bay Maritime Museum in St. Michaels, Maryland. Editorial credit: George Sheldon /

The town promoting itself as a "Historic Charm, Nautical Adventure, Romantic Spaces" is a must-visit in Maryland. Choose a fetching bed and breakfast along the eye-candy main thoroughfare—a real delight on a stroll with attractions for all groups and ages. It is one of the state's most walkable streets, filled with a variety of whimsical boutiques and great seafood restaurants to peruse, relax, and repeat. Visit St. Michaels during the summer or winter holidays, when fun and magic take place along the decorated downtown with local events.

The small waterside town with quaint, old-fashioned houses, boutiques, and restaurants concentrated along the main street is also home to the astounding river harbor, steps away from the hotspots. The beautiful river views greet you with the town's best attraction, the iconic screw-pile design of a 19th-century Hooper Strait Light, one of only four along the Chesapeake Bay. Enjoy a scenic coffee break at a terraced cafe with the sea breeze in your face amid charming maritime culture sights with deep roots in seafaring.


Maryland State Route 851 (Main Street) at Sandosky Road and Oklahoma Avenue in Sykesville, Carroll County, Maryland
Maryland State Route 851 (Main Street) at Sandosky Road and Oklahoma Avenue in Sykesville, Carroll County, Maryland. Image credit: Famartin, via Wikimedia Commons.

Sykesville, a cool town in central Maryland, boasts easy access to its most-worthy Main Street with a weekend's worth of browseable hotspots. Discover all the charm that Sykesville has to offer on a getaway from the city, with its cozy atmosphere and feel-good small-town pursuits. The recent winner of America's coolest small town, Sykesville, has also literally won "best main street" competitions.

Find an epic mix of historic sights and modern-day attractions like atmospheric pubs, cozy cafes, and various shops along the main thoroughfare behind the beautiful building facades of yesteryear. Slow down and savor the unique culture of a local lifestyle on a stroll through farmers' markets, local eateries, charming shops, and regular festivals on a family-friendly getaway into always-good times.


Loys Station Covered Bridge in Thurmont Maryland
Loys Station Covered Bridge in Thurmont, Maryland.

This astounding small town is a mere hop away from Frederick at the edge of the Appalachian Mountains. Thurmont is a destination for historians with vestiges dating to its mid-18th-century establishments and for nature lovers at the gateway to the beautiful Catoctin Mountain Park. Discover the vibrant, historic main street next to the refreshing outdoors on a memorable weekend getaway from the city. The small town of around 7,000 people, founded in 1751 with 1,000 residents, a fire department, a bank, and two hotels, is now declared a National Main Street by the National Trust for Historic Preservation.

Enjoy plenty of warm-weather opportunities through Cunningham Falls State Park and Catoctin Mountain Park, like biking, hiking, and swimming. Discover the area's covered bridges, orchards, and wineries in any season, and visit the Catoctin Wildlife Preserve and Zoo. The small town charms with sights and epic pursuits along the unique red-brick buildings that veil countless local independent businesses. Visit the annual Catoctin Colorfest arts and crafts festival along the main street, which draws some 125,000 people the second week of October.

The "Old Line State" since the Civil War was divided over whether to join the Union and remained a slave state for most of the war, while in 1862, it held the bloodiest one-day battle in the history of the US, the Battle of Antietam. Visit one of these 12 towns for history-strewn thoroughfares with endless cultural pursuits and learn about the state's pivotal role in American history before and after it was named a state in 1788. Enjoy shopping and dining for every taste and diversify your stay with no common stop on a getaway along the main street alone.

Join the local lifestyle to absorb all that the state's got on a relaxing stroll along beautiful architecture left from the time when Maryland was one of the original 13 colonels in the 18th century. Every stroll down these exciting main streets is a cultural one with a perfect mix of scenic views, epic pursuits, and hotspots to sit back and relax any way you like. Slow down to the local pace and feel its beating main street heart, with spirited festivals and events like farmer's markets and in between boutiques and cafes.

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