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Things to do this May in Berlin

When’s the last time you visited America’s Coolest Small Town? Not just drove through or stopped in for lunch, but really took the time to explore Berlin? If it’s been awhile, this May just might be the perfect time to rediscover the quaint, historic town, 10 miles from the beach and in the center of all of Worcester County’s natural beauty and charm. 

10 reasons to visit Berlin, Maryland

 Berlin, Maryland Welcome to America’s Coolest Small Town Berlin, MD Navigation The town of Berlin, otherwise referred to as ‘America’s Coolest Small Town,’ (see below) is just 10 miles from the beach, but it’s more than a tourist destination for sunshine and summer fun.

Take the day, the weekend or an entire week-long vacation to stroll downtown and see the new boutiques lining Main Street; enjoy a meal at a beloved local restaurant like The Globe or Rayne’s Reef; take in the history and old-fashioned atmosphere of the Atlantic Hotel; and attend one of the fantastic annual events happening this May in Berlin. 

representational art at the globe
See some art while you’re in town, too- the Worcester County Arts Council is based in Berlin, along with several galleries, including the upstairs of The Globe! (The restaurant’s downstairs dining room also features local artwork, pictured here.)

Jazz & Blues, Wine & Brews

May 4, 10 a.m.-6 p.m.

Jazz and blues? Wine and brews? Yes, it’s all happening in Berlin on Saturday, May 4, when jazz and blues musicians take to two stages in Berlin and provide the soundtrack to shopping Berlin’s quaint downtown shops and the craft vendors throughout town. There will also be food vendors, a beer garden and 60 different wines from around the world available to taste for $35. Admission to the festival is free. 

Reggae Play Day

May 10, 5-9 p.m.

“Can’t make it to Jamaica this year? No problem mon… We’ll bring Jamaica to you!” It’s all about the music on Reggae Play Day, where Jah Works and the Zion Reggae Band will be performing. Sponsored by Ocean98, Reggae Play Day also features food vendors, wine and a beer garden.

Spring Cruisers in Berlin

May 18, 10 a.m.-2 p.m.

Classic cars and cruisers line the streets of Main Street Berlin during this annual Cruisin’ event. Come see all the retro cars and hot rods on a beautiful spring day in America’s coolest small town.

Memorial Day at the Monument

May 26, 8-8:30 a.m.

Begin celebrating Memorial Day a day early at Berlin’s Memorial Day at the Monument event, where a ceremony to honor our veterans will be held at the Veterans Monument on the corner of West and Main Street. Sponsored by the American Legions. 

Memorial Day Parade at Henry Park

May 27, 11 a.m.-5 p.m.

Stick around Berlin for the weekend and attend the Memorial Day Parade at Henry Park! The parade begins at 11 a.m. at Stephen Decatur Middle School and features cars, bands, dancing and music. The parade will march down to Henry Park, where music, vendors, food and games keep the celebration going until 5 p.m. Sponsored by the Berlin Community Improvement Association. 

Kristin is a writer and photographer in Ocean City, Maryland, and is the content manager for OceanCity.com and other State Ventures, LLC sites. She loves getting reader-submitted stories and photos, so send her an email anytime. She also works part-time at the Art League of Ocean City and the Ocean City Film Festival and lives just off the peninsula with her dog and fiancé. Her photos can be found on Instagram @oc_kristin.

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