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Pair History With Fun at These Eastern Shore Destinations

Pair History With Fun at These Eastern Shore Destinations

cowboy jumping through rope

As summer comes to a close, now is a great time to make the trek across the Chesapeake Bay Bridge to the Eastern Shore. Walking the Ocean City boardwalk (constructed in 1900) and digging your toes in the sand are pleasant experiences no matter the time of year. But our beautiful beaches aren’t the only reason to head east. Take your time and explore Maryland’s history and culture through these four Eastern Shore destinations.

Go for a spin at the oldest amusement park in the United States

Maryland’s Eastern Shore is home to the oldest family-owned amusement park in the United States! Trimper Rides was founded in 1893 and is still spinning today.

dad and son on Trimper Rides
Photo Credit: Trimper Rides

Daniel and Margaret Trimper opened two hotels, the Sea Bright and the Eastern Shore, just three years after arriving in Ocean City, Maryland. After a storm damaged the Sea Bright in 1900, they rebuilt it in the style of Windsor Castle in England. Their hotels, amusement park, and theatre were known as the Windsor Resort. Twelve years later, Daniel purchased a 50-foot Herschell-Spillman Carousel, which still operates in the park today. When it was installed, it was one of the biggest in the country!

old black and white photo of carousel
Photo Credit: Trimper Rides

The park expanded over the century to include a haunted house, designed and built by a Ringling Brother’s art director, a Ferris wheel, several rides, and shops. Today it is owned and operated by the fifth generation of Trimpers. Over a century has passed since its founding, but parts of the park remain the same. Visitors can still get spooked in the haunted house or enjoy the beauty and novelty of the antique rides and ticket booths (all in working condition) spread throughout the indoor portion of the park.

Giddy up to the Wild West

If you’re a Maryland local, you may have a nostalgic heart for Enchanted Forest, the fairytale-inspired amusement park in Ellicott City. (If you’re a preservationist like me, you also cheered along as many of the pieces were preserved and restored.) But Enchanted Forest wasn’t the only well-known creation from Maryland-based Adler Display in the 1950s and 60s. 

Frontier Town Wild West Theme Park
Photo Credit: Frontier Town Wild West Theme Park

Adler Display also built Frontier Town in Berlin, a western-themed park outside of Ocean City where you can take in a show, pan for gold, ride a stagecoach, and even eat inside a replica of a saloon.

Celebrate the culture of the Chesapeake Bay 

Established in 1965, the Chesapeake Bay Maritime Museum in St. Michaels is dedicated to preserving and exploring the history, environment, and culture of the Chesapeake Bay region. The museum includes a floating fleet of historic boats, 12 exhibition buildings, and changing special exhibitions along the Miles River and St. Michaels’ harbor.

The Chesapeake Bay Maritime Museum, courtesy of George Sass
Photo Credit: The Chesapeake Bay Maritime Museum, courtesy of George Sass

If you’re visiting on the weekend between Memorial Day and October, take advantage of the hour-long “highlights tour” included with the admission price. You’ll visit the Working Shipyard, 1879 Hooper Strait Lighthouse, Oystering on the Chesapeake, Floating Fleet, and Waterman’s Wharf exhibitions,

Learn the incredible legacy of an iconic freedom fighter

Harriet Tubman was an escaped enslaved person, abolitionist, suffragist, nurse/spy for the Union during the Civil War, and the most well-known conductor on the Underground Railroad. 

Tubman risked her life to guide over 70 enslaved people north to new lives of freedom.

A visitor looks out over Stewart's Canal at dusk. Enslaved and free African Americans dug for seven miles through marshland to create Joseph Stewart's canal. Here Harriet Tubman likely worked alongside her father, floating timber and other goods to ships waiting at local wharves.
Photo Credit: National Park Service
A visitor looks out over Stewart’s Canal at dusk. Enslaved and free African Americans dug for seven miles through marshland to create Joseph Stewart’s canal. Here Harriet Tubman likely worked alongside her father, floating timber and other goods to ships waiting at local wharves.

Harriet Tubman Underground Railroad National Historical Park in Church Creek (outside of Cambridge) preserves the same landscapes she used to carry herself and others away from slavery. Learn about her extraordinary legacy as you take an audio tour while driving along the scenic byway through the Eastern Shore. (Learn more about the Underground Railroad in Maryland here.)


Lead Photo: Frontier Town Wild West Theme Park

About the Author

Dana Cohen is the director of communications at Preservation Maryland. She works with their team and partners to tell the stories about their important preservation work and highlight what makes Maryland’s historic buildings, communities, and landscapes special. She currently lives in Towson with her husband, two kids, and two cats in a quaint cape cod.

Maryland Road Trips is a part of Postern Publishing.
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