Buildings opening onto street in small town of Havre de Grace, Maryland.

8 Quintessential Maryland Towns

Sandwiched between the rugged peaks of the Blue Ridge Mountains and the sublime coastline along the Chesapeake Bay and Atlantic Ocean, Maryland is home to diverse natural landscapes. Its winning blend of rich history, vibrant culture, and outdoor opportunities makes it a sweet spot for travelers on the East Coast. Unlike the bustling metro areas of Baltimore, a selection of little-known destinations on the fringes of the state truly bring out the charm of the Old Line State.

From idyllic waterfront villages like Havre de Grace, steeped in maritime heritage, to the lush mountain enclave of Cumberland, these quintessential Maryland towns embody the spirit of the state. Each locale offers a unique glimpse into the past while providing modern amenities and activities, inviting you to experience the state's charm and hospitality firsthand.

Mount Airy

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

Mount Airy is often celebrated for its beautiful countryside scenery, punctuated by sprawling farms, vineyards, and orchards. Newcomers can look forward to remarkable tasting opportunities at Linganore Winecellars, which sits on a rolling 230-acre property and produces over thirty wine varieties. The Mount Airy Historic District is a must-visit. It takes strollers on an exciting journey through time with its fine display of structures from the 1800s and 1900s. You can stop by the Mount Airy Museum, housed inside the historic Train Station, to learn about the town's dynamic past.

The downtown area expertly mixes the new with the old, allowing tourists to experience its more contemporary side with a retail therapy session at the Mount Airy Shopping Center. This bustling mall offers an eclectic blend of retail stores and dining venues featuring regional and national brands.

Chestertown

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

Chestertown finds the ideal balance between rich history, exceptional waterfront scenery, and a vibrant art landscape to guarantee tourists fun experiences. Since its founding in the early 1800s, the town has amassed a storied heritage that you can delve into at the Historical Society of Kent County. Thousands of items pertinent to Chestertown's history help bring landmark events in the area's past back to life. The local art community resides at the Garfield Center for the Arts, where enthusiasts converge for entertaining stage presentations.

With ready access to the water, Chestertown is a popular destination for aquatic fun lovers. The Chester River Packet Company takes guests on scenic cruises along the slow-flowing waters of the Chester River, with delicious crab cakes served on deck.

Cumberland

Overlooking Cumberland, Maryland.
Overlooking Cumberland, Maryland.

Boasting unbeatable vistas of the Allegheny Mountains, this rural community charms visitors with enchanting sightseeing excursions with a ride on the Western Maryland Scenic Railroad. This fun trip traverses the mountainous landscapes of the state's backcountry inside a classic steam locomotive. Cumberland's history stretches back to the 18th century and maintains numerous period landmarks to prove it. Prominent among them is George Washington's Headquarters, a rustic log cabin that President George Washington once used as a military command post.

Exploring downtown Cumberland reveals a delectable display of restaurants, galleries, and museums. While there is much to see and do, art connoisseurs easily gravitate towards the Cumberland Theatre to catch a compelling lineup of dramas, plays, musicals, and concerts.

St. Michaels

Autumn colors on the Chesapeake Bay Shore and Harbor in St Michaels, Maryland
Autumn colors on the Chesapeake Bay Shore and Harbor in St Michaels, Maryland

From exploring historic sites and enjoying the outdoors to indulging in sumptuous seafood, this lovely Chesapeake Bay town has no shortage of fun pursuits for vacationers. A trip to the Chesapeake Bay Maritime Museum allows guests to check out a world-class collection of interactive artifacts in an 18-acre museum. Not far off, the photogenic Hooper Strait Lighthouse from 1879 always makes for a photo op. There is more to uncover about local history at the St. Michaels Museum, which showcases the town's evolution from Colonial days to the present.

One of the most popular visitor experiences features getting on the water for a unique perspective of St. Michael. Fortunately, numerous local outfitters, including St. Michaels Harbor Shuttle, organize boating tours on the Miles River.

Thurmont

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

This charming mountain village, a few miles from the Pennsylvania border, is surrounded by rugged wilderness, making it one of the quintessential Maryland towns for ardent adventurers. It is home to Cunningham Falls State Park, which offers isolated hiking trails, camping sites, and a 43-acre reservoir. However, the highlight is a 78-foot waterfall, which provides a spectacular backdrop for a photo. Thurmont presents more opportunities at the Catoctin Mountain Park, where 25 miles of trails thrust hikers into the heart of the backcountry.

Animal lovers will enjoy touring the Catoctin Wildlife Preserve. This 100-acre zoo provides a sanctuary for native and exotic species, promising an opportunity for rare encounters with zebras, panthers, bears, and other wildlife.

Berlin

Downtown street in Berlin, Maryland
Downtown Berlin, Maryland. Image credit Alexanderstock23 via Shutterstock

Berlin captivates first-timers with a Victorian town center, quaint museums, beautiful nature areas, and a lively restaurant scene. The downtown district hosts a fair share of significant points of interest, including Burley Oak Brewing Company. This is an excellent stop to sample the area's craft brewery culture. Furthermore, the Berlin Farmers Market breathes life into the sleepy corridor as local vendors, farmers, bakers, and crafters display a colorful array of merchandise for potential buyers.

Also, don't leave without checking out Berlin's beautiful coast at the Assateague State Park. This premier outdoor space presents fine opportunities to spot a range of birds, reptiles, and mammals, with the major attraction being wild ponies roaming the sandy shores.

Havre De Grace

 Panoramic view of the coast in Havre de Grace in Maryland.
Panoramic view of the coast in Havre de Grace in Maryland.

Havre de Grace is a romantic village on the mouth of the Susquehanna River with a mixed bag of surprises awaiting first-timers. It has something for everyone, and historically inclined tourists will find the ideal pursuit at the Havre de Grace Maritime Museum. Browsing the different artifacts and archives in the museum provides an idea of the region's commercial crabbing and fishing heritage.

The Friends-Concord Point Lighthouse remains a conspicuous landmark and an important historical marker since its installation in 1827. The lighthouse overlooks the ocean and sits along the path of the Havre de Grace Promenade. On this beautiful boardwalk, sightseers take lazy strolls and soak in unbeatable vistas of the Chesapeake Bay-Susquehanna River junction.

Ocean City

 People walking along the Ocean City Boardwalk in Maryland.
People walking along the Ocean City Boardwalk in Maryland. Editorial credit: George Sheldon / Shutterstock.com

Most travelers planning to explore the Maryland coast without dealing with choking crowds visit this lovely resort city on the Atlantic Ocean shores. Ocean City boasts an extensive shoreline, inviting beachgoers to stroll on smooth sands and soak in the toasty waters at Ocean City Beach. This popular getaway has a family-friendly atmosphere with concession stands, restaurants, arcades, and other amenities. The historic Ocean City Boardwalk presents access to carnival rides, fancy eateries, and souvenir shops in a socially upbeat atmosphere. It is an excellent alternative for those who don't want to get on the sand.

Also, take some time to discover the town's life-saving heritage at the Ocean City Life-Saving Museum. This interesting station was established in 1891 and holds a collection of eye-opening exhibits.

Final Thought

Maryland's iconic small towns are a testament to the state's absorbing history, colorful culture, delicious cuisine, and stunning natural beauty in the United States. Each town invites visitors to experience its unique character and hospitality, whether visiting St. Michaels or Ocean City. Embrace the spirit of the Old Line State as you discover these quintessential towns in Maryland for a unique slice of charm and a warm welcome that will leave you wanting to return time and time again.

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