- March 28, 2024
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WINTER GARDEN — Jay Conn, the recreation director for the city of Winter Garden, remembers the day he saved a camper’s life.
“It was on a field trip, and we were laughing and eating lunch,” he said. “I looked over, and he couldn’t breathe and had this scared look on his face. I gave him the Heimlich (Maneuver), and the piece came out.”
Conn, who was hired by the city in 1998, could tell stories all day about his adventures with the Winter Garden Recreation Department. He has been with the city for 17 years, the first seven of which were as recreation supervisor. He became director when longtime employee Larry Caskey retired from the position.
Now it’s Conn’s turn to say goodbye to the rec department; his last day was Friday, July 24. He has taken the position of leisure services director with the city of Maitland’s Parks and Recreation Department.
“I still have 25 years of working ahead of me, and I felt like I needed some new challenges,” Conn said. “I feel like the (Winter Garden) department is in a good place, and there are good programs and good staff.”
Conn listed all the programs and accomplishments he’s proud of.
“I’m really proud of the fact that we got a very large and active youth soccer league at Braddock Park after that was constructed,” he said. “I’m happy that we built a lot of partnerships with groups and were able to use those resources to provide programs to the community.”
This includes an agreement with Crealde School of Art and the Orange County Extension Service to offer classes at the Jessie Brock Community Center.
But there’s one in particular that stands out.
“Probably what I’m most proud of here is the Kid’s Café through Second Harvest Food Bank at the Maxey Community Center,” Conn said. “We provide meals to kids in need and after-school enrichment services there.”
GROWTH
The city’s recreation program has continually grown under Conn’s leadership. The department’s sparse beginnings were in a tiny office above the concession stand at the ballfields in Veterans Memorial Park, when Caskey was at the helm. Conn was hired as supervisor after Caskey expanded the recreational offerings and had the office moved to a location closer to Newton Park, Farnsworth Pool and Tanner Hall, where most of the activities took place.
When Tanner was renovated in 1999 and rec access was limited, the Fire Station Recreation Center on South Boyd Street was opened, and activities and classes were moved to this location. Conn spent his first summer in this building, which once housed the city’s fire department, and remained there until 2010.
Conn said he and Caskey were a good team for seven years, creating programs that appealed to citizens of all ages. When Caskey retired in 2005, he said he knew he was leaving his position in good hands.
“Jay’s a good recreation person,” Caskey had said. “He’s just a real go-getter. He knows our system. He’s going to be real good for the department and the city.”
In 2010, Conn assisted in the department’s move to the Jessie Brock Community Center, which took over the buildings that remained of the old Dillard Street Elementary School.
He has overseen many summer programs in 17 years, all of which required a devoted staff. Conn said it has been a delight to see some of the children who grew up participating in the rec programs return as staff members.
“They’ve turned into great adults,” he said.
CONTINUED SUCCESS
As the city grew, Conn’s responsibilities grew, too, with the addition of several parks. The newest, Warrior Park, is south of the Roper YMCA and serves as a popular place for residents to walk their dogs. Picnic areas are set up, as well.
Conn said the long-term plan is to develop this property as a trailhead for a southern trail system in Winter Garden.
The Lulu Creek Trail, a spur off the West Orange Trail at Division Street, was added in 2013. Conn said there are plans to eventually connect it to Newton Park on Lake Apopka.
He was involved in the early stages of Tucker Ranch park on the west side of the city, too.
Winter Garden officials currently are looking for a replacement director. Conn has no plans to move closer to Maitland and will remain in Winter Garden with his wife, Teresa, and two sons.
“I’ve really enjoyed my time here in Winter Garden,” Conn said. “I’ve been lucky enough to work with some wonderful staff who have done a lot to expand the recreation program for the citizens.”
Sebrenia Brown was hired by the Winter Garden Rec Department at the same time as Conn, and she said she is sad to see him go.
“When he told me he was leaving, all I could do was drop my head so he wouldn’t see the tears,” Brown said. “Jay was a jewel to work for, and in all the years we worked together, we never had a cross or mean word between us. Jay was the kind of person that just didn’t believe in being mean or harsh but was about being fair.
“He would never expect you to do something that he wouldn’t do,” Brown said. “We both thought of this place as being our second home.”
Although it will be tough for Conn to leave his co-workers and friends, he is grateful for the opportunities the city has afforded him and is deeply satisfied with all the special events that brought so many residents together through the years.
“It’s been terrific to think that we had a little part to play in helping to make Winter Garden a better place to live and visit and play,” Conn said.
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1998: Jay Conn is hired as recreation supervisor.
1999: The old fire station on South Boyd Street is used as a center for activities.
2005: Conn is promoted to recreation director after Larry Caskey retires.
2006: Kid’s Café is started at the Maxey Community Center.
2009: Braddock Park is constructed in south Winter Garden.
2010: Recreation department moves its offices from the old, wooden yellow house near Lake Apopka to the Jessie Brock Community Center on Dillard Street and begins offering programs through Crealde School of Art and Orange County Extension Service.
2013: Lulu Creek Trail, a spur off the West Orange Trail at Division Street, is created.
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Contact Amy Quesinberry Rhode at [email protected].