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.
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.
