13 Of The Most Welcoming Towns In Maryland
Maryland's unique cultural diversity, Southern hospitality, and small-town riches make it one of the most welcoming states on the East Coast. Beyond Baltimore's rowdy streets and stifling crowds, the Old Line State is dotted with charming towns where community pride takes precedence and genuine hospitality fuels everyday life. In these close-knit communities, everybody seems to know everybody, local businesses thrive on familiar faces, and visitors are often treated like old friends.
From admiring the soothing beauty of countryside landscapes and dining in down-to-earth eateries to partaking in longstanding traditions among friendly locals, these gems offer respite from life's daily routine. From Pocomoke City to Berlin, find welcoming towns in Maryland to visit.
Pocomoke City
Pocomoke City's nickname, "Friendliest Town in the Eastern Shore," rings true for first-timers in the community, given the numerous opportunities to socialize and interact with strangers. This begins at the Mar-Va Theater Performing Arts Center, where everybody can watch theatrical presentations in a family-friendly atmosphere. Every Friday, the Pocomoke City Farmers Market transforms the downtown region into one big social party as multiple vendors and potential buyers come together for a fun trade day.
The town also charms guests with a lineup of unmissable festivals, including the annual Delmarva Decoy Heritage Festival, which celebrates the Eastern Shore tradition of carving duck decoys for hunting.
Berlin
Historic Berlin is home to a vibrant commercial district that is always buzzing with activity, ranging from local businesses and seasonal events to annual events, allowing strangers to feel a sense of belonging from sustained human interactions. The Berlin Farmers Market is an excellent example of why the town feels welcoming to first-timers. This is a chance to mingle with over 50 regional growers and more locals looking for something nice to buy.
The annual Bathtub Races is another whimsical tradition that has brought townsfolk together for over three decades, featuring friendly yet competitive races, costumes, and a parade down Main Street. Berlin's inclusivity shows during the eagerly anticipated Oktoberfest, which embraces German heritage with authentic German food, beer, and music in a festive environment.
Havre De Grace
Under 50 minutes from Baltimore, Havre de Grace makes it easy for tourists to encounter locals and engage in heartfelt conversations due to its long lineup of year-round events. Whichever season you visit, there is always something happening to bring people together, including the Waterfront Festival in the fall. This mixes a boat parade, seafood treats, live music, and a fundraising event. Meanwhile, the Decoy & Wildlife Art Festival headlines the major occasions in summer. This unites decoy markers, crafters, carvers, and fans of the industry for one of the largest gatherings celebrating the tradition.
However, the warm season hosts a bulk of the annual events in Havre de Grace, and most tourists target the Art, Wine, Jazz & Soul Festival to coincide with their vacation. This well-attended event features everything from live music and wine tastings to art demonstrations, creating an exciting overall vibe.
Thurmont
Thurmont is fun to visit any time of the year, but especially pleasant in the fall. This is when the many farms and orchards in the community host various seasonal festivals and events, allowing families to come together and welcome the foliage and harvest in style. For instance, Magnolia Meadow Farms hosts a beautiful Fall Festival with hayrides, a corn maze, mini ziplines, jumping pillows, and more to entertain the townspeople. Autumn also coincides with the Catoctin Colorfest, which draws over 125,000 attendees for a massive celebration of the arts and crafts.
But you don't have to visit during the festivals to feel welcomed in Thurmont. On Saturday, the Thurmont Main Street Farmers Market presents an excellent chance for genuine interactions with farmers and vendors.
Mount Airy
Mount Airy is a close-knit town in central Maryland with a thriving agricultural heritage, evidenced by sprawling farms, orchards, and vineyards. The Mount Airy Farmers Market allows local farmers to come together and share their agrarian bounty with the community every Wednesday, offering an ideal setting for townsfolk to mingle. Thanks to an abundance of farms in the town, the autumn season comes with multiple themed festivals. The Fall Fun Festival at Gaver Farm is among the season's highlights, drawing families with pumpkin pickings, animal petting, a corn maze, and giant slides.
Mount Airy demonstrates its curious connection with Europe with the annual Mid-Maryland Celtic Festival. This whimsical, family-friendly affair celebrates Scottish heritage through bagpipe music, Highland games, traditional crafts, and other activities, leaving a lasting impression on vacationers.
Darlington
This tiny village in northeast Harford County has a charismatic vibe that shows in the genuine way locals interact. Almost everyone is on a first-name basis, a credit to the fun festivals that always bring townsfolk together. Darlington is best known for the Darlington Apple Festival, held in the fall to celebrate the harvest with delicious food, unique crafts, and live entertainment. The town also hosts the annual Ramble Festival, which brings three days of nonstop music entertainment, featuring jam, funk, and brass music genres.
Darlington even designates a festival for those who don't indulge in alcohol to make them feel included. Anahata's Purpose is an interesting four-day wellness festival incorporating live music, workshops, and other activities in an alcohol-free environment.
Oakland
Small-town charm and unprecedented natural beauty make visitors feel welcomed in this tiny Western Maryland town. Oakland comes alive in the fall when the foliage starts transforming, and the community marks this with the Autumn Glory Festival. This anticipated family affair sees five days of parades, corn mazes, crafts, great food, and concerts to spread cheer throughout the community. Meanwhile, the Little Yough Summer Musical Festival brings a series of month-long concerts to downtown Oakland to entertain all generations in the community.
Besides the festivals, Oakland is home to Our Town Theatre, a vital cultural hub that nurtures creativity in the town. This is where residents come together to rally behind homegrown talent by watching them perform engaging plays, musicals, and other forms of performance art.
St. Michaels
St. Michaels is easily one of the most welcoming towns in Maryland, a credit to its soothing waterfront setting along the Chesapeake Bay, and a consistent lineup of fun, family-friendly events across the calendar. The St. Michaels Running Festival is a major tourist draw in the town, and features different races for various age groups to help participants maintain a healthy lifestyle. Also, WineFest at St. Michaels calls wine lovers and wine makers from around the region to enjoy tasty local wines during a two-day celebration.
Finally, the Chesapeake Bay Maritime Museum hosts the Eastern Shore Sea Glass and Coastal Arts Festival every spring, which draws at least 100 craft exhibitors and vendors and features an exciting costume contest.
Easton
Easton is a likable small town on Maryland's Eastern Shore known for its small-town flair and a shared love for the arts. The community hosts multiple farmers' markets that allow sustained gatherings, including the Amish Country Farmers' Market. Besides interacting with impressionable Amish vendors, tourists shop for and buy pretty Amish crafts, baked goods, and furniture. Elsewhere, the annual Waterfowl Festival celebrates the arts and nature during a three-day event, attracting participants with crafts, music, and unique heritage.
The town also gives beer lovers something to look forward to with the Easton Beer Fest. Since 2016, multiple craft beer makers from around the area have participated in the festivities, alongside food vendors and live entertainers.
Crisfield
The "Seafood Capital of the World" hosts a long lineup of annual festivals and fairs celebrating its dynamic heritage and many facets. Crisfield's National Hard Crab Derby pays tribute to its seafood heritage with various family-friendly activities. This fun event features crab cooking, crab races, and other crab-themed contests over the Labor Day weekend. Furthermore, the Crisfield Heritage Festival celebrates community and family, promising fun activities for all ages. This fall event features kids' entertainment, great food, craft vendors, and live music.
Meanwhile, the Crisfield faithful demonstrate their community pride during the Big Little Townfest. Held in July, this family-centric affair welcomes everyone for a fun beach party, heritage events, and the World's Largest Rubber Duck.
Timonium
This small town in Baltimore County is famous for hosting the annual Maryland State Fair. Thousands of thrilled participants gather at the Maryland State Fair Grounds every August to celebrate the state's premier agricultural show. This yearly jamboree supports and promotes the region's farming industry through concerts, free entertainment, animal shows, and delicious food. Timonium also holds the Festival of Trees at the same grounds to celebrate the Kennedy Krieger Institute.
Finally, the Timonium Beer, Bourbon & BBQ Festival is a large food festival in the town. This headlines the fall events in Timonium and features a selection of beer, barbecue, bluegrass music, biscuits, and more.
Centreville
Centreville is a tiny village in Queen Anne's County that takes pride in its robust sense of community. The town hosts one of the liveliest 4th of July parades, with participants of all ages painting the downtown streets with a spectrum of colors. Also, the annual Queen Anne's County Fair welcomes tourists to join the townsfolk in celebrating the agricultural heritage. The event incorporates an array of family-friendly activities to entertain all the attendees, from livestock shows and rodeo showcases to craft vendors and live concerts.
Those visiting Centreville in summer can make a point of attending Maryland Crafted: Centreville. This enthralling event allows tourists to mingle with at least 40 makers from across the state and sample some of the finest craft beers, wines, spirits, crafts, and live music created in the state.
Ocean City
This charming coastal town by the Atlantic Ocean feels like a never-ending beach party with its stacked lineup of festivals across the seasons. The Oceans Calling Festival is one of the premier events along the shore, with dozens of regional and national acts treating attendees to electrifying musical performances on stage. Movie lovers and movie creators meet in the town every spring for the Ocean City Film Festival, which screens at least 100 national and international films of diverse genres.
Meanwhile, the Ocean City Sunfest is a must-experience event and one of the biggest outdoor festivals along the East Coast. It attracts tens of thousands annually and promises four days of music, crafts, food, art, and fun.
These welcoming towns in Maryland demonstrate their charm and community spirit through vibrant festivals that celebrate local culture, history, and seasonal traditions of the United States. From crab derbies in Crisfield and Celtic gatherings in Mount Airy to apple fests in Darlington, each town offers visitors an authentic experience. Whether you are drawn to coastal celebrations or mountain harvests, Maryland's small towns open their arms with hospitality and joy, no matter the season you choose to visit.
