Windsor Resort, Inc
Hospitality has long been at the heart of Trimper’s Rides, the longest running family-owned carnival in America. German immigrants Daniel and Margaret Trimper ran the Silver Dollar Bar in Baltimore, Maryland, but after visiting nearby Ocean City in 1890, the couple sold their business and invested their life in the beachside town. They bought their first seaside property in 1892 and opened two hotels—Eastern Shore and The Sea Bright—the next year.
At the time, the boardwalk was nothing more than a collection of boards that business owners would lay down on the sand by day and pull up each night. But Daniel saw potential in the town as more and more visitors discovered Ocean City. He expanded his business to entertainment: billiards, boxing matches, a shooting gallery, gambling, a roller rink, a bar, dancing, a carousel and even a live alligator exhibit.
After a major storm pummeled the town in 1900, Daniel remodeled his properties to resemble Windsor Castle in England and dubbed the makeover, Windsor Resort. He also added a theater and amusement park. In 1912, Daniel purchased a 50-food masterpiece carousel from the Herschell-Spillman Company. Still in operation, it’s one of the oldest operating carousels in the country. (A sister carousel once ran at Coney Island but was destroyed by fire.)
Over the past hundred years, Daniel Trimper and his descendants have added and lovingly maintained historic rides: Kiddie Carousel, Ferris Wheel, The Rock and Roll Matterhorn, The Himalaya, The Pirates Cove, The Haunted House, and The Balloon Ride.
In the 1950s, they introduced games like Frog Bog and Whack A Mole, and calls of “step right up” rang down the boardwalk. The family launched Ocean City’s tallest roller coaster, The Tidal Wave, in the 1980s, along with the Inlet Village shops and Harbour Watch restaurant.
Trimper Rides celebrated its 125th year anniversary in 2018, and two years later, a new board of directors recommitted their efforts to upholding the Trimper Family legacy in Ocean City. They hunted down and brought back vintage rides like the Tilt a Whirl and Round Up, and introduced Ocean City’s newest thriller: The Super Shot Drop Tower.
While honoring the traditions and memories of generations of visitors, Trimpers also saw modern upgrades in 2020 with free WiFi, electronic Thrill Swipe Passes, and new food and beverage outlets. It’s now the site of Ocean City’s farmers market, and the future home of summer concert series.