Berlin sits on a 300-acre tract that was originally the Burley Plantation. As Native American hunting paths became colonial highways, the plantation found itself at a crossroads: the post road north to Philadelphia met the Sinepuxent Road east to the barrier islands. A tavern, blacksmith shop, and livery opened at the intersection, and a town grew up around them. Berlin was incorporated in 1868, three years after the Civil War, and the arrival of the Delaware, Maryland and Virginia Railroad within the decade made it the commercial hub of upper Worcester County. In 1895 a fire leveled much of the downtown. The rebuilding produced the streetscape of Victorian brick storefronts in Queen Anne, Italianate, and Second Empire styles that still defines Main Street today. Forty-seven of the historic structures appear on the National Register of Historic Places. Berlin is a Maryland Main Street Community - a deliberate designation that has supported decades of careful preservation and incremental revival.

Hollywood discovered Berlin twice in three years. In 1999, Paramount Pictures filmed Runaway Bride with Richard Gere and Julia Roberts using Main Street as the fictional town of Hale, Maryland. The production crew altered storefronts, planted fake mailboxes, and dressed the street to match the script. Three years later, Disney returned for Tuck Everlasting (2002) with Sissy Spacek, Ben Kingsley, and William Hurt. This time Berlin played Treegap, the small American town where Winnie Foster meets the immortal Tuck family. The production teams kept much of the work subtle - period storefronts were already there, the architecture worked - and locals walked their dogs past camera trucks for weeks. Both films make the town look distinctively like itself, which is the trick of small-town location work: dress the place up enough to fit the story, but not enough to lose what made the location worth choosing. Berlin played itself twice with slightly different names.

Just east of Berlin, on Glen Riddle Farm, stood the training stables of Samuel D. Riddle. Riddle owned a chestnut colt named Man o' War, who in 1919 and 1920 ran one of the most dominant racing campaigns in American thoroughbred history. The horse won 20 of his 21 starts, set five American records, and earned the lifetime nickname Big Red. His only loss, in the 1919 Sanford Memorial Stakes, came after the starter gave the field a chaotic break; his name became a byword for raw speed. Man o' War was sired in Kentucky but bred and trained at Glen Riddle Farm in Worcester County, and he died in 1947 and was originally buried at Faraway Farm before being reinterred in 1977 at the Kentucky Horse Park in Lexington under a bronze statue. Riddle later bought Man o' War's son War Admiral, the 1937 Triple Crown winner who lost the legendary Seabiscuit match race in 1938. Two of the greatest racehorses of the twentieth century were stabled, at different points, in the same farm a mile from Berlin's town hall.

Atlantic General Hospital, a 62-bed facility founded in 1993, sits in Berlin. On September 17, 1996, former Vice President Spiro Agnew died there of acute leukemia at age 77. Agnew had resigned the vice presidency in October 1973 amid a corruption investigation - he eventually pleaded no contest to one count of tax evasion, the only U.S. vice president to leave office under that kind of cloud until that point. He had retired to Worcester County, where he played golf at Ocean City courses and kept a low profile. His death at the Berlin hospital made local news but barely national news; the country had moved on. The hospital itself is a regional facility serving the lower Eastern Shore, with an emergency room, a cancer center, and a bariatric clinic. The fact that a former vice president died here - one of very few to leave office before their term ended - is the kind of detail Berlin does not advertise but also does not hide.

In 2014, Budget Travel magazine named Berlin America's Coolest Small Town - an honor that drew busloads of weekend tourists and pushed downtown rents higher than the residents had ever seen. The designation also accelerated the revival of the commercial district that had started in the late 1980s. Restaurants opened in the Victorian storefronts. Boutiques replaced hardware stores. The Globe Theater, a 1917 vaudeville house, reopened as a restaurant and music venue. Tucked into Worcester County's interior, Berlin offers what Ocean City cannot: a walkable downtown without traffic, with original architecture rather than imitation. It sits eight miles inland from the beach, close enough to be the back-door dinner-and-drinks alternative to the boardwalk crowds. The 2010 census counted 4,485 residents. The town has grown steadily since. Notable past residents include Stephen Decatur, the naval officer born nearby in 1779; David H. Jarvis, the Revenue Cutter Service officer who in 1897 led the dogsled rescue of eight stranded whaling ships off Point Barrow, Alaska; and Charles Tindley, the Methodist minister and composer who in 1901 wrote 'I'll Overcome Some Day,' the hymn that became the basis for the civil rights anthem We Shall Overcome.