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Planners Hope Osceola Park Car Show Unites Alums, Sparks Interest
By Brittany Polito, iBerkshires Staff
04:55PM / Sunday, September 12, 2021
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Organizers of a car show at Osceola Park hope it will spark interest in revitalizing the park. Investments have been made in other city parks, but not yet at Osceola.

PITTSFIELD, Mass. — Robert Connors grew up as an abutter to Osceola Park and said that his time spent playing there was a "way of life."  Jerry LaBerteaux lives across the street from the park and is disappointed that its rope tow hasn't been functioning for three winters now.
The two banded together to plan a car show and Osceola Park reunion event which will unite the grown-up children who called the space a second home and spark interest for its revitalization.
"My back yard on West Housatonic Street in Pittsfield abutted Osceola Park and visiting the park was an all-day joy year-round in the late 1950s and early 1960s, there even was a ski tow and an ice-skating rink with a warming shed and night lights, today's youngsters don't really know what they're missing out on," Connors said.
"This event is an opportunity for the attendees to explore this hidden gem of a park and it could spark a revitalization of Osceola Park so that "kids of all ages" can enjoy the park as much as many of us did, we hope that attendees echo our desires for the Pittsfield Parks Commission to proceed with needed upgrades and improvements at the park."
The free event will take place on Saturday, Sept. 18, at the park from 10 a.m. to 3 p.m. There is open admission for the car show with a suggested donation and trophies will be given out for "Best of Show" and "Attendee Pick."
From noon to 2, Osceola alumni are encouraged to congregate at a bring your own picnic celebration to share memories and reflect on the good old days at the park.
There will also be a 50/50 raffle with prizes donated by local businesses.

To support the costs of the event, they started a fundraiser on the Gofundme platform with a goal of raising $1,300 to cover the obtaining of portable bathrooms, police detail, and permitting. Any extra donations will go to the park.

"We wanted to plant some trees and maybe additional picnic tables, things like that," LaBerteaux said.
He said the Osceola Park Car Show was started because of Connor's wish to unite with old friends and his own wish to see the space get some TLC.
Back in its heyday over 50 years ago, the park boasted an ice skating rink, a ski slope, and a warming shed for winter activities.  In the summer, there was full-day programming for children including sports, crafts, and movies at night.
Unfortunately, Osceola's well-known rope tow that ascends up its 500-foot hill has been out of commission for the last few years.
The park's playground equipment is also reportedly dated, the basketball area has weeds growing through the concrete, and the baseball field has unmarked bases.
"We've seen the stuff that city's done with Clapp Park, Durant Park, and The Common and stuff, and we've noticed that the last three years, the city has not operated the rope tow, so we did an inquiry about it and the city said last year, that they didn't have budgeted money to operate it," LaBerteaux said.
"And then I saw that they actually had budget money allocated for this year or next year to do some improvements to the park so I thought, 'Well, if [Connors] is having an alumni picnic, this is a great way to tie this together to get community interest to get some improvements."
There have been a number of park renovations in the city, including the West Side Riverway Park on Dewey Avenue, Clapp Park on West Housatonic Street, and the recent facelift of Kellog Park at the corner of Lincoln and Wellington Streets.
Connors remembers his time at the park fondly. He writes vignettes inspired by boyhood adventures that are published on his Facebook page called "Osceola Park Memories."
As a regular at the park from 1954 to 1966, Connors said he feels for modern-day children who don't have the same kind of outdoor facilities offered to them. When he was a boy, Pittsfield had around 20 city parks equipped with staff members.
In August, the event was unanimously approved by the Pittsfield Parks Commission and the panel voiced support for the revitalization efforts.
"It's mainly to help the kids get some new playground equipment, because the swings and slides, they're really old," LaBerteaux said.
"Because again, we live right across from the park, we see a lot of kids, parents bring their kids so I know the park could get utilized."
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