It all started with a recommendation in the mid-1950s.

Tom Flanagan’s mother, Betty, told her stepsister, Peggy Flaherty, that Ocean City was a fine place for a summer vacation. In 1961, their families, plus a handful of others, started an annual summer vacation.

Over the years, the vacation trips became something of an occasion. Five generations have now stepped foot onto the barrier island resort town.

“Five families came the first year, ’61, with the Flanagans,” said Lee Ann Dobson, daughter of Leo and Peggy Flaherty, and a second-generation vacationer to Ocean City.

"Every year more people would join us and as we got married and had children, our in-laws would come and bring more,” she added. “Then, our kids all got married and had kids. Then their in-laws come.”

Nancy McGarvey, 90, is the last member of that first generation, and she’s still making the trip. She was a close friend to Dobson’s mother.

The Pittsburgh-area clan recently completed their 60th annual trip with 141 people attending.

At first, the trips were housed in the former Olympic condominiums on 40th Street. In 1965, they moved to the Coffin condos on 41st Street. When the Coffin apartments were demolished and replaced with the Surf Watch, they moved to Ocean Point III on 41st Street, where they’ve stayed ever since.

The trips are typically jam-packed with an assortment of traditions. This year there was a “Halloween in July” parade down 41st Street, Pictionary on the beach and a “Crazy Bridge Tournament,” a Spades-like game with a winner-take-all cash prize.

They started the trip with their “Light Up Night” tradition.

“We did it back in the early ‘80s,” Dobson said. “My dad wanted to have a light-up night because we were all in those. Everybody went all out with all 14 porches. My dad was in the middle of the street at 9 p.m. and says ‘Light up!’ and everybody plugged in. It was like (1989 film) ‘Christmas Vacation.’ People were driving down the street wondering what’s going on.”

Traditions come and go with every passing year. Some are formal, some aren’t, said Terry Evangelista, Dobson’s sister.

“Every year someone usually plans a big happy hour,” Evangelista said. “We’ve had Halloween, Christmas in July. We’ve had a toga party, wedding reception, Steeler parties, (an Academy Awards offshoot called) the Sterling Awards.”

Added Tom Flanagan, Dobson’s cousin, “People have been engaged here.”

After 60 years, businesses around town have gotten to know the clan.

Seacrets, Cork Bar, Belly Busters, Fat Daddy’s and Buxy’s Salty Dog Saloon all made the cut among their favorite spots in town. In 2006 they even dedicated a tree to Dobson’s father, Leo “Dedo” McGarvey, in the park behind Buxy’s on 28th Street.

Dobson’s younger sister, Mary Anne McGarvey, lived with Buxy’s founder Douglas “Buxy” Buxbaum for a spell. She lived in Ocean City year-round for seven years during the 1990s.

One of their traditions has been having the younger attendees pick up large orders of donuts from the Fractured Prune and then “deliver” them to everyone else for tips.

“Fractured Prune was across the street back in the ‘70s,” Dobson said. “They would take orders from us and the kids would go every day — every day.”

“Every year when we pulled in (to town) they had on their sign ‘Welcome Pittsburgh,’” Evangelista said. “They knew we were coming.”

Dobson’s grandchildren carry on the tradition now.

“That’s been a part of our story — traditions that ebb and flow and we’ve tried to keep as many going as we can over the years,” said their father, Geoff Dobson, Lee Ann’s son. “Sometimes they go away for a little while and then they come back based on the ages of the people. You need to have kids a certain age to do certain things.”

With five generations in the books, Geoff said he hopes the tradition goes on “forever.”

“The nice thing is there’s a couple of options with different-sized places,” he said. “Those were two-bedroom places. A lot of us have bigger families now so it’s nice to have options for everyone to stay on 41st Street.”

Like McGarvey, Lee Ann and her peers plan to enjoy Ocean City every summer as long as they can. And even though the younger generations have years ahead of them, they’re committed to keeping the tradition alive.

“When our kids were younger we’d ask them if they wanted to go to Ocean City or Disney World,” Lee Ann said. “And they would rather come here.”

This story appears in the print version of Ocean City Today on July 30, 2021.

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