Berlin, Maryland. Local businesses in Berlin, Maryland. Image credit: Philip N Young via Flickr.com.

9 Maryland Small Towns With Unmatched Friendliness

Maryland boasts a winning mix of features that make it one of the most welcoming states you can visit. It enjoys economic stability, has a strong sense of community, and the social scene is vibrant with numerous entertainment companies. While this may not be too obvious when strolling through the crowded streets of Baltimore, the rarely explored sides of the Old Line State are chock-full of welcoming municipalities, where the phrase "Southern hospitality" seems to have taken root.

These likeable localities make visitors feel at home from the moment they arrive, with residents keen to welcome them into their fold. From Eastern Shore gems like Pocomoke City to Chesapeake Bay favorites like Ocean City, these Maryland small towns demonstrate unrivalled hospitality.

Crisfield

Main Street in Crisfield, Maryland.
Main Street in Crisfield, Maryland. By Idawriter, CC BY-SA 3.0, Wikimedia Commons

Crisfield is a small, beautiful town on the scenic Chesapeake Bay shores with a laid-back charm and comfortable weather year-round. Its waterfront setting draws many visitors to the water, compelling them to take mellow-paced sightseeing cruises courtesy of local outfitters like Experience Smith Island. Guests can sample the iconic Chesapeake Bay cuisine in numerous downtown restaurants. At Linton's Seafood, the trademark crab dishes are heavenly, and the service is top-notch. The Crisfield Entertainment Arts and Entertainment District hosts a charismatic community of creatives, featuring talented artists, makers, crafters, musicians, and writers.

It is an excellent escape to get in touch with your artistic side while browsing art galleries and interacting with live performers. Crisfield also hosts numerous festivals throughout the year, giving townsfolk a reason to come together for fun. The BIG Little Townfest is among the most anticipated and unravels along the stunning Chesapeake Bay shoreline.

Cumberland

Fall scenery in Cumberland, Maryland.
Fall scenery in Cumberland, Maryland. Editorial credit: Kosoff / Shutterstock.com.

This delightful United States mountain community in Western Maryland entices visitors with its unmatched outdoor scenery, vibrant art scene, and receptive residents. The Cumberland Visitor Center provides a glimpse of the townspeople's warmth as they welcome newcomers to the city, providing them with an elaborate summary of the best things to do and top experiences to try out. Cumberland's magical natural scenery is best explored aboard the Western Maryland Scenic Railway. Guests enjoy a solemn sightseeing excursion through the vast wilderness of the Allegheny Mountains.

The arts community takes shelter at the Cumberland Theatre. This lively cultural hub stages diverse live performances to entertain residents and unite them through a mutual cause to support local talent. Finally, regional events like the Taco Fest help demonstrate a sense of camaraderie in the area.

Berlin

Downtown Berlin, Maryland
Downtown Berlin, Maryland. Image credit Alexanderstock23 Shutterstock

A slow pace of life and a strong sense of community in Berlin allow visitors to warm up to their new surroundings seamlessly. Residents are known for their friendliness; you can tell this from the many fun experiences along the Berlin Commercial District. Burley Oak Taproom & Brewing Company has a warm atmosphere that invites newcomers to sample Berlin's delicious craft brews and socialize with vivacious patrons. Meanwhile, those who enjoy nostalgic encounters can find fascinating artifacts depicting the past at the Calvin B. Taylor House.

Beyond the downtown, the atmosphere at the Assateague State Park best personifies the amiable nature of the people. This storybook natural space features pristine beaches and marshes, with roaming wild horses casually walking around the shores. It is an idyllic escape for nature lovers and wildlife enthusiasts.

Snow Hill

Bates Memorial United Methodist Church, Snow Hill, Maryland.
Bates Memorial United Methodist Church, Snow Hill, Maryland. Image credit Anthony Frisina via Shutterstock

This unassuming village on the banks of the Pocomoke River combines small-town flair and beautiful nature to ensure guests have a comfortable time. It beckons outdoor immersion throughout the sprawling wilderness of the Pocomoke River State Park. Spreading over 14,000 acres, adventurers of all types gather here for endless recreation, from swimming to hiking and camping. Downtown Snow Hill hosts an eclectic mix of attractions that first-timers will fancy exploring. If you love to shop, you can pass by Sassy Girl Boutique for unique gift items and trendy fashion accessories.

Elsewhere, the Julia A. Purnell Museum offers a glimpse of the town's past with a dynamic collection of memorabilia and artifacts, some stretching back to the 16th century. Snow Hill's long lineup of festivals gives the community a reason to come together, and guests are welcome to join them for a great time during the Snow Hill Seafood Festival.

Hampstead

Northbound Main St, Hampstead, Maryland.
Northbound Main St, Hampstead, Maryland.

Hampstead's small-town America reputation manifests through the warm personality of its residents, pristine nature areas, and farm-to-table eats. Tourists are thrust into the heart of the wilderness at Prettyboy Reservoir Park, which features a mix of dense woodlands and calm waters. Activities here range from hiking and hunting to boating and fishing. Tourists with an appetite can taste diverse local delicacies at the many downtown eateries. If you have a thing for Italian, Fratelli's Italian Restaurant promises to impress you with authentic dishes like baked manicotti.

Later, a pint of great-tasting craft beer from Pipe the Side Brewing Company is the perfect follow-up. While Hampstead hosts many events annually, the Hampstead Volunteer Fire Company Carnival is the most anticipated.

Pocomoke City

Rustic buildings along the main street in Pocomoke City, Maryland
Rustic buildings along the main street in Pocomoke City, Maryland. Editorial credit: Kosoff / Shutterstock.com

With a nickname like "the friendliest town on the Eastern Shore," Pocomoke City ranks among Maryland small towns where you will come across genuine Southern hospitality. The people are very welcoming and make you feel part of the community. This is true for anyone watching a live show at the Mar-Va Performing Arts Center. The atmosphere is always buzzing as local performers entertain the audience with dramas, musicals, and comedies. Meanwhile, family-friendly events like the Downtown Pocomoke Fall Festival allow newcomers and natives to mingle in a superb setting.

Those who enjoy green spaces can venture outdoors along the scenic Cypress Park Nature Trail. This is an excellent pursuit for tourists seeking to unplug in a peaceful environment devoid of the downtown noise. Lastly, if you have some change to spare, consider searching for a vintage souvenir at Flea Market 14 Antiques.

Thurmont

Downtown Thurmont, Maryland
Downtown Thurmont, Maryland. Image: Andrew Bain, Wikimedia Commons.

This pleasant mountain town in Frederick County is known as an outdoor haven, offering numerous opportunities to explore virgin nature getaways. The Catoctin Mountain peaks highlight Thurmont's beautiful scenery, beckoning adventurers to take on rugged trails through Catoctin Mountain Park. These are perfect for mountain bikers and hikers. More fun awaits at Cunningham Falls State Park, whose crowning jewel is the 78-foot Cunningham Falls. Considered the state's highest cascading waterfall, it is a terrific visual spectacle that nature photographers can't get enough of.

Beyond the outdoor immersion, Thurmont offers tasty local wines to get you in the holiday mood. You can tour Catoctin Breeze Vineyard to enjoy some of the best offerings and revel in the views of the Blue Ridge Mountains. Finally, schedule your visit to fall within the Catoctin Colorfest to partake in a longstanding tradition celebrating art, food, heritage, and more.

Ocean City

View of the boardwalk in Ocean City, Maryland
View of the boardwalk in Ocean City, Maryland. Editorial credit: eurobanks / Shutterstock.com

Ocean City's combination of sun, sea, and sand makes it one of the most sought-after East Coast destinations for a summer vacation. Unlike the city, the crowds are thinner, and tourists enjoy a sense of privacy and comfort when enjoying the sandy shores of Ocean City Beach. But if you don't mind a little company, the Ocean City Boardwalk has an eclectic mix of restaurants, gift shops, souvenir outlets, and juice bars, resulting in a vibrant hub perfect for mingling and socializing.

Those visiting with children can head to Jolly Roger Amusement Park for fun moments with loved ones, featuring a Ferris wheel, water slides, and thrill rides. Also, mark your calendar so you do not miss the Ocean Calling Festival and experience the town's more outgoing personality.

Havre De Grace

A vibrant ice cream bench in Havre de Grace, Maryland.
A vibrant ice cream bench in Havre de Grace, Maryland. Image credit George Sheldon via Shutterstock

Havre de Grace is another charming city on the Chesapeake Bay where life moves at an easygoing pace. Visitors experience its rich history and culture across multiple downtown museums. The Havre de Grace Maritime Museum focuses on the region's nautical history, displaying artifacts related to various expeditions on the surrounding waters through the years. Havre de Grace sits on the confluence of the Chesapeake Bay and the Susquehanna River, and visitors can witness the magical scene of the two water bodies interacting from the Havre de Grace Promenade.

This scenic platform is a popular escape for trekkers and nature photographers throughout the year. Meanwhile, those who relish genuine conversations with the locals can make the most of the Havre de Grace Farmers Market. This weekly gathering brings together exuberant local vendors eager to get into a conversation with any potential buyer.

Final Thought

While Maryland is nationally renowned for its Civil War history, vibrant cultural landscape, and exquisite natural scenery, its hospitality is the icing on the cake for tourists expecting a remarkable experience. Next time you plan to check out the Old Line State, take a detour from the major cities to discover the above Maryland small towns with unmatched friendliness. Opportunities abound to make lasting memories amidst welcoming townsfolk, whether you are mingling with festival goers in Hampstead or chilling by the ocean in Berlin.

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