An ice cream sundae bench on the sidewalk in the business district area of the bay town.

9 of the Most Welcoming Towns in Maryland

Maryland, recognized for its trademark hospitality, stands out among the Southern states. It is rich in colonial history, natural beauty, and coastal vistas, making it a dream destination for those traveling the East Coast. The state's small towns provide an ideal base for exploring Maryland's diverse offerings.

These towns not only exude a delightful small-town vibe but are also home to charming, close-knit communities. The locals are known for their warmth and openness to newcomers. Visitors exploring the rich historical heritage, unique cultural traditions, and stunning natural landscapes of these towns are assured of a rare and fulfilling experience. Suitable for solo travelers, friends, or families, these Maryland towns represent the epitome of Southern charm.

Pocomoke City

Street view in Pocomoke City, Maryland
Street view in Pocomoke City, Maryland, via Kosoff /

Referred to as “the friendliest town on the Eastern Shore,” Pocomoke City is a small community with around 4,500 residents in Worcester County. The town offers a tranquil atmosphere and picturesque natural spaces, ideal for relaxation and contemplation. The nearly 4-mile-long Cypress Park Nature Trail provides a tranquil environment for nature lovers. Walking through the town center, visitors are greeted by friendly locals who engage in conversation, adding to the sense of community.

In Pocomoke City, several family-friendly museums, such as the Costen House Museum and Sturgis One Room School Museum, allow visitors to delve into the town's heritage. The historic Mar-Va Theater Performing Arts Center hosts live performances, offering a glimpse into the town's cultural scene. For a taste of local hospitality and cuisine, Don’s Seafood & Chicken House is a popular spot, renowned for its delectable dishes and welcoming atmosphere

Havre de Grace

Aerial view of Havre de Grace, Maryland
Aerial view of Havre de Grace, Maryland, in autumn. Image credit Wirestock Creators via Shutterstock.

Located at the head of Chesapeake Bay, Havre de Grace is a captivating waterfront community. It strikes an excellent balance between suburban tranquility and city-like vibrancy, offering a pleasant contrast to the busier streets of nearby Baltimore. Visitors often marvel at the town's stunning natural scenery, best enjoyed along the Havre de Grace Promenade. The area's peaceful atmosphere and picturesque water views provide a perfect setting for relaxation.

The town is also rich in history, as seen in its numerous landmarks. The 1827 Concord Point Lighthouse, an iconic monument listed on the National Register of Historic Places, stands as a testament to this heritage. For a glimpse into the Victorian era, the Spencer Silver Mansion offers rustic accommodations with its 19th-century façade. Meanwhile, Millard Tydings Memorial Park is a favorite local hangout, ideal for interacting with residents and enjoying community activities.

Mount Airy

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

Strategically positioned between Baltimore and Washington D.C., Mount Airy serves as a haven away from the hustle and bustle of these larger cities. This modest community, home to about 10,000 residents, is one of the most sought-after places to live in Maryland, drawing professionals, retirees, and families alike. It boasts a low crime rate, small-town allure, and ample outdoor activities. The Audrey Carroll Audubon Sanctuary offers a serene environment with diverse habitats and wildlife, perfect for nature enthusiasts.

The vibrant Main Street in downtown Mount Airy features a variety of quaint cafes, trendy restaurants, unique galleries, and boutique shops. CarterQue BBQ & Grilling Co. is renowned for its exceptional meats, including chicken, beef, pork, and seafood. The town is also close to several wineries, such as Loew Vineyards, which is a prime destination for those interested in the local wine scene.


Historic downtown of Berlin, Maryland.
Historic downtown of Berlin, Maryland.

Berlin, a small village in Worcester County, Maryland, is home to about 5,000 residents and is rich in history. Contrary to what its name might suggest, Berlin was not named after the German capital but was inspired by a local tavern named “Burleigh Inn.” History enthusiasts have much to explore in Berlin, with landmarks such as Burley Manor and the Calvin B. Taylor House (which is temporarily closed), showcasing artifacts and memorabilia dating back to the 1830s.

Additionally, Berlin offers stunning outdoor scenery and adventurous activities. At Assateague State Park, visitors and locals alike can engage in swimming, camping, fishing, and sunbathing. The park is also known for its herd of wild horses, offering a distinctive wildlife viewing opportunity.


Corner of Main and Water in downtown Thurmont
Corner of Main and Water in downtown Thurmont, By Andrew Bain - Own work, CC BY-SA 3.0, File:Thurmont MD Corner of Main and Water.jpg - Wikimedia Commons

Despite its small size, Thurmont is a town with a unique appeal, characterized by a slow-paced and relaxed atmosphere. The residents are notably friendly and down-to-earth. The town becomes particularly vibrant during its various festivals, with Colorfest being a highlight. This family-friendly art event features over 650 craft vendors, displaying an array of local creativity.

Thurmont is also home to several serene and inviting attractions. The Catoctin Wildlife Preserve offers an opportunity to connect with nature and wildlife. For those interested in agriculture and scenic beauty, the Catoctin Mountain Orchard is an ideal visit, where guests can observe the harvesting of fresh produce in a picturesque setting.


View north along Maryland State Route 194 (York Street) at Maryland State Route 140 (Baltimore Street) in Taneytown, Carroll County, Maryland
View north along Maryland State Route 194 (York Street) at Maryland State Route 140 (Baltimore Street) in Taneytown, Carroll County, Maryland, By Famartin - Own work, CC BY-SA 4.0, Wikimedia Commons

Once renowned as Maryland’s safest town, Taneytown offers a quiet, relaxed ambiance. With fewer than 8,000 residents, it's ideal for those preferring a slower pace of life, complemented by beautiful natural surroundings. The 40-acre Taneytown Memorial Park, featuring shaded picnic areas, green lawns, and child-friendly amenities, serves as a community hub.

Taneytown’s historical heritage dates back to its founding in 1754. Its historic downtown corridor is lined with historical wooden buildings showcasing quaint architecture. Notable landmarks include the Antrim 1844, a 19th-century hotel listed on the National Register of Historic Places.


The entrance to an antique and souvenir shop in Leonardtown, Maryland
The entrance to an antique and souvenir shop in Leonardtown, Maryland

DatinThe entrance to an antique and souvenir shop in Leonardtown, Marylandg back to the 1660s, Leonardtown's downtown area is a rich mosaic of Maryland history. As the seat of St. Mary’s County, this town of about 5,000 people is known for its friendly community. Visitors can explore historic structures like the Tudor Hill Mansion from 1798 and the Moll Dyer Rock, steeped in local legend. The scenic Leonardtown Wharf Park offers panoramic views of Breton Bay along its concrete walkway.

A focal point for community interaction is Shepherd’s Old Field Market, a bustling hub for shopping and socializing. Leonardtown also celebrates various festivals, including the National Oyster Shucking Championship, offering a glimpse into local traditions and a taste of the area’s seafood.


Northbound on Main Street in Hampstead
Northbound on Main Street in Hampstead

Hampstead, a quaint town in Maryland, offers a safe and nurturing environment. With a population of just over 6,000, this town, established in the 1880s, is known for its fertile agricultural lands and small-town charm set amidst lush greenery. The low population contributes to a minimal crime rate, making Hampstead an inviting destination for those looking to enjoy its attractions. Lions Club Park is one of several open spaces where the community engages in recreational activities like baseball and football. For those seeking a more solitary experience in nature, Prettyboy Reservoir Park is ideal for hiking, birdwatching, angling, and hunting in a scenic setting. A popular spot to mingle with locals is the Greenmount Bowl, offering family-friendly bowling experiences.

Final Thoughts

Maryland attracts travelers from across the United States for various reasons, including its stunning natural landscapes, rich historical heritage, and exciting outdoor activities. However, the defining feature of Maryland is the welcoming spirit of its small-town communities, creating a home-away-from-home feeling for visitors. These towns are excellent starting points for anyone planning to explore the state.

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