The summer he was 19, Joe Kroart threw some paintings in his car and drove down Route 50 to his childhood paradise, Ocean City.

It was the mid-1960s and several stately old hotels with tall pillars and wide porches still presided over the Boardwalk. North of 40th Street, there were few buildings and the sand dunes seemed to stretch on forever. The old-timers still reminisced about the hurricane that sliced open the inlet.

Kroart slept in a hotel storeroom at night and he sold his paintings on the Boardwalk by day. There, plank by plank, he built by hand his business, Ocean Gallery, which remains open today.

“Everybody’s childhood in Maryland seems to tie into Ocean City somehow,” said Kroart, 84, who has chatted with generations of beachgoers from his sign-covered storefront. “There’s a deep personal feeling in Ocean City.”

It’s been 150 years since the first hotel opened in Ocean City, setting in motion the transformation of a sleepy fishing village into the state’s top summer resort. To mark the anniversary, the town opened a new museum highlighting Ocean City’s Black and Indigenous history, revisited the stories of its founding mothers, the “Petticoat Regime,” and planned 150 days of special events.

Remnants of the Ocean City’s previous incarnations linger among the bustle of new businesses and national chains. Visitors still lick a cone of Kohr Bros’ frozen custard, splash malt vinegar on Thrasher’s French Fries and ride the 1912 carousel at Trimper Rides amusement park, just as generations before them.

“Ocean City is a multi-generational experience,” said Brandon Seidl, 41, who has written two books about the town’s history. “You can experience something today that your grandparents were able to experience. There aren’t that many places like that any more.”

In the beginning

The earliest residents of the barrier island we call Ocean City were indigenous people, most notably the Assateague, whose name means “swiftly moving water,” according to exhibits in the Museum of Ocean City, which opened in a former downtown bank building last September.

The indigenous people lived near the sea in summer, catching fish and crabs, and then moved inland when the harsh winter winds blew. Colonists forced them to move to inland reservations in the late 1600s and early 1700s.

For hundreds of years, the spit of land was sparsely settled by white fishing families. Then in 1875, the first formal hotel, The Atlantic, was opened by a team of businessmen led by Lemuel Showell, a wealthy Worcester County landowner, according to Gordon E. Katz, an accountant and historian who wrote a book about the hotel.

To bring visitors to his hotel, Showell also built a railroad that ran from Salisbury to Berlin and then expanded the line to carry them directly to the hotel, Katz said.

Meanwhile, an enterprising group of women, mostly wives of fishermen, were transforming their homes into guest houses, explained Christine Okerblom, the curator of the Ocean City Life-Saving Station Museum and the new history museum.

The women moved all their children into one bedroom during the summer months so the other rooms could rented to vacationers. In time, the women, who were called “The Petticoat Regime,” expanded their businesses to form many of the town’s early hotels, Okerblom said.

Among them was Rosalie Tilghman Shreve, a widow and mother of two young children, who opened one of Ocean City’s most elegant hotels, The Plimhimmon, in 1894. The Plimhimmon featured a grand open fireplace, cupola and wide porch but its biggest draw was that it was the first hotel in town to boast both electricity and running water.

Early visitors to Ocean City rode horses along the beach, waded into the water in elaborate bathing costumes and hunted the vast quantities of birds along the dunes. A book of diaries and photos of Robert Craighead Walker, who visited Ocean City as a boy in the first decades of the 1900s, depicts him holding a heron he had shot and recounts him eating “shore birds on toast” for dinner.

As humans altered the ecosystem of the shore, the forces of nature unmade and remade the resort town.

Fires, including a massive blaze in 1925, obliterated many of the grand old hotels. A ferocious 1933 hurricane wiped away the beach between Ocean City and Assateague. But this act of destruction was also an act of creation— the newly formed inlet drew sport fishers who could now travel by boat from the Isle of Wight Bay to the ocean.

A hidden history

While Black men and women worked at many of Ocean City’s hotels in the early 1900s, segregation laws prevented them from patronizing the businesses in which they worked. A smattering of Black-owned businesses catered to them, including Aralanta’s Boarding House, The White Cottage and the Ocean Wave Hotel, which hosted a “remarkably brilliant” “grand soiree,” according to a 1900 article.

A 1927 Baltimore Afro-American article highlighted the disparities between Ocean City’s white visitors and Black employees.

“For the former there are comfortable accommodations, with personal service for all needs, bathing yachting, fishing, golf, rest, dancing, automobiles,” read the article, which is excerpted in the new museum. “For the latter: work, eating, sleeping, cards, talking, walking, and bathing, if one is willing to walk a mile or more to and from the segregated beach.”

Black people were relegated to swimming on the beaches north of the Boardwalk, Katz, the local historian, said. As new hotels and motels appeared, Black folks were forced to swim at beaches farther north. Black people were only allowed to fully patronize the Boardwalk and swim at prime beaches during a designated period in September after most white guests had left.

Efforts are underway to preserve and turn into a museum one historic Black-owned property, The Henry Hotel, which reportedly hosted Black luminaries including Cab Calloway, Duke Ellington and Louis Armstrong.

Ocean City desegregated in 1965 although Black business leaders, residents and guests repeatedly raised concerns about discrimination in the following decades. In 1986, the Worcester County branch of the N.A.A.C.P. led a demonstration on the Boardwalk to protest discriminatory hiring practices. Six years later, the organization pushed Ocean City officials to put more images of Black families on tourism materials.

In 2021, after a video went viral of Ocean City police officers using Tasers on a group of unarmed Black teens, a Washington Post investigation found police there used force disproportionately more often with Black people.

While the 8 million people who visit Ocean City annually reflect a racially and ethnically diverse group of people, about 92 percent of the town’s 7,000 year round residents are white.

Rapid growth and quirky attractions

As Ocean City was desegregating, it was also rapidly growing northward.

Head north on Coastal Highway to take a tour of each era of Ocean City’s growth. The serene wooden hotels of the early 1900s give way to the mod motels of the 1950s and 60s: The Thunderbird, The Eden-Roc, the Flamingo.

Then there are the condominiums constructed in the 1970s and 80s, which seem to get a little taller the farther north you drive.

Threaded throughout are sites of cherished childhood memories: the amusement parks, mini golf courses, ice cream parlors and candy stores.

For Seidl, a childhood visit to Trimper’s Haunted House sparked a passion for learning about Ocean City’s rides and attractions. Seidl has co-written a book about Trimper’s and one titled Ocean City Oddities, which chronicles wonders such as Princess Donaldina, the mechanical fortune teller at Playland, Randy Hofman’s sand sculptures and the neon cans and bottle that have been dancing on the sign for Anthony’s Liquors since 1982.

Seidl is also the co-creator of a website documenting “dark rides,” such as haunted houses, created by Bill Tracy in the middle of the last century. Just eight of the 81 projects Tracy designed remain and of those, the Trimper’s Haunted House is the best, said Seidl.

“The Haunted House, for me, is Ocean City,” said Seidl. “The vibrant colors, the black lights, mixing the old with the new.”

Trimper’s Haunted House opened 61 years ago. A second story was added in 1988 and the attraction was renovated in 2012, Seidl said, but the overall vibe — like a campy trip to the Twilight Zone — hasn’t changed over the years.

The surrounding attractions on the lower Boardwalk feel similarly timeless: Trimper’s carousel, the fishing pier, the arcades, and the Ocean City Life-Saving Museum.

Dolle’s Candyland stands in the same spot at Wicomico Street and the Boardwalk where Anna Dolle Bushnell’s grandfather and great-grandfather began selling salt water taffy in 1910.

“My family came down here at the invitation of the Trimpers,” said Dolle Bushnell, 46, president of Dolle’s Candyland. “They were carousel people. Half the family made the mechanics and the other half made the horses.”

After a catastrophic 1925 fire, the Dolle family switched from running a carousel to making taffy. Dolle Bushnell said they still follow the same recipe, although flavors have changed in response to customer demand. Black walnut and wintergreen are out; buttered popcorn and salted butterscotch are in.

Dolle Bushnell recalls working at the candy shop as a teen in the summer, then heading to Trimper’s on her lunch break. The owners of the amusement park, old friends of her family, had given her an all-you-could-ride pass.

After a whirl on the merry-go-round, Dolle Bushnell would eat a slice of pizza and sit and watch the ocean before heading back to the candy shop.

There’s something special about the flavors you can only find on the Boardwalk, Dolle Bushnell said.

“You can’t get this anywhere else,” she said. “It’s always Ocean City for us.”