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For half a century its big neon sign has drawn generations of locals and holidaymakers into a world of family fun.

Tayside and Fife’s biggest indoor fun fair Pleasureland has been an amusements mecca beside Arbroath FC’s Gayfield Park for all of those 50 years.

From wide-eyed youngsters who can’t make up their mind what to try first, to the oldies ready to treat the grandkids on a day out at the switchies.

And the O’Brien family behind the seafront success story is ready to mark the milestone with a big birthday bash.

A day and night of celebration is lined up for Saturday August 16.

Pleasureland founder Jimmy O’Brien can expect to see some familiar faces, from regular customers to the staff he says have been pivotal to the attraction’s popularity from its beginnings.

The O’Brien family’s roots stretch back more than two centuries of delivering fairground fun.

Jimmy’s dad, also Jimmy, first arrived in Arbroath with his father Henry’s travelling show in the early 1920’s.

But the family tree goes all the way to the original Barnum and Bailey’s Circus dubbed the Greatest Show on Earth.

Jimmy’s mother was a former trapeze artist and circus horseback ballerina.

The family travelled all the main fairs in Scotland as a carnival tenant before going it alone with a set of chair-o-planes and a Foden traction engine called Dreadnought.

Arbroath was one of their regular stops.  Originally on the West Links where the town’s play area, paddling pool and crazy golf are now, then Inchcape Park near the Signal Tower.

And it led to Jimmy making the leap of faith to build Pleasureland.

He said: “We always came to Arbroath for the summer.

“During the Glasgow Fair this place was bouncing.”

But then, as now for outdoor attractions and events, the switchies were at the mercy of the east coast climate.

“When there were high winds it was difficult to operate,” says Jimmy, “So setting up an indoor funfair was a no-brainer.”

As if to reinforce the point, Storm Floris is battering Pleasureland when we visit.

But she’s drowned out by the music, machines and voices of excited children filling the building.

Jimmy, 77, adds: “From the germ of an idea, it took seven years before we finally got planning permission.

“But it was the right decision.  When people go on holiday, they want to be entertained, and that’s what we’re all about.

“I consider us to be the best family attraction for holidaymakers in the town.”

Pleasureland has always been a family affair.

Jimmy and wife Ellen are still around most days.  Daughters Lisa and Justine were also involved, and it is now son Todd who is at the helm.

Todd, 38, carved a different path as a top-level ski instructor before returning to the fold.

He’s seen the attraction through the rollercoaster of Covid and the challenge of maintaining its appeal in the digital era.

A fleet of new solar-powered bumper cars are as popular as ever.

And the venue’s centrepiece since day one has been its spectacular waltzer from the early 1960s.

“Being under cover in one place has helped us keep it in good condition,” says Todd.

“It still requires a lot of work to do that, but it’s worth it.  There are fairground enthusiasts who come up here to take photographs of it because it’s so original.”

He adds: “We invest heavily in new games every year to try to give people something new.

“We’ve also got to be quite hot on things like social media.”

And the family are united in their praise for the staff who have worked there over the past 50 years, including the current complement of 45.

The special family day will include face painting, a fire engine visit and magic show.

Wristbands will be half price for the day, with 50% of all proceeds going to Angus Carers Centre.

Then, from 8pm, Hometown DJ Van Damn will take over for a night of music and memories.

Jimmy adds: “We’ve seen generations of families come here.  I might not remember their names, but I’m quite good with faces, so hopefully we’ll see some of them for the anniversary and in the years to come.

“I hope Pleasureland will be around for a good bit yet.”

This article appeared in The Courier on 6 August 2025