by Beth Kassab | Aug 25, 2025 | Arts and Culture, City Commission, Historic Preservation
New Park Avenue archway underscores historic Winter Park
A group of private donors combined with public dollars made the $400,000 project possible
Aug. 25, 2025
By Beth Kassab
Winter Park leaders on Monday celebrated the installation of the first of two archways that will bookend Park Avenue.
The $400,000 pair of signs emphasize the city’s commitment to historic preservation and were one of the last projects spearheaded by former Planning & Zoning Director Jeff Briggs before he retired at the start of the year.
Mayor Sheila DeCiccio gives remarks at an event to celebrate the new signs on Monday.
The City Commission provided about half the money for the arches made by Don Bell Signs and eight private donors covered the remainder.
Briggs has said the calls for donations were among the “easiest” he ever made with lots of enthusiasm for the markers that call even more attention to Winter Park’s popular dining and retail corridor, which was added to the National Register of Historic Places in 2011.
The sign on the north end stands at the intersection of Park and Webster avenues next to the public golf course known as the Winter Park Nine and in sight of historic home-turned-venue Casa Feliz.
The city seal now adorns City Hall as part of a refresh of the building over the summer.
A second arch on the south end near Park and Aloma avenues and just across the street from Rollins College is slated to go up at the end of September.
Private donors to the cause are: Rick Baldwin; Jim and Diana Barnes; Mike and Gail Winn; the Allan E. and Linda S. Keen Family; Larry and Joy Williams Private Foundation; Edyth Bush Charitable Foundation; Joe and Sarah Galloway Foundation and the Elizabeth Morse Genius Foundation.
The signs aren’t the only noticeable public upgrade along Park Avenue. City Hall, at the intersection of Lyman Avenue is sporting a new paint job with the city seal, featuring a peacock, now prominently displayed to passersby.
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by Beth Kassab | Aug 14, 2025 | City Commission, News, Uncategorized
Playhouse gets lease and city looks for Seven Oaks Park developer
The City Commission also took steps to limit residential pickleball courts
Aug. 14, 2025
By Beth Kassab
The Winter Park Playhouse is closer to its goal of starting a $10 million renovation of the professional musical theater, which includes the purchase of the building by the city.
On Wednesday, the City Commission approved two critical steps — the funding agreement for Orange County to provide $8 million through a grant of tourism tax dollars and a lease agreement with the city to rent the building for $1 a year.
A rendering shows the proposed renovations for the Winter Park Playhouse.
The lease also allows the playhouse to request up to a $600,000 “bridge loan” if it has not met its private fundraising requirement of $1.6 million to receive the county dollars at the start of the project. The playhouse must show it’s raised at least $1 million to request the loan.
“A lot of faith there,” Commissioner Marty Sullivan said. “But I’ve got faith in the playhouse to make this work.”
Heather Alexander, co-founder and executive director, said the playhouse has already secured $1 million in private funds toward the goal and has pledges totaling more than $600,000 set to come in over the the next three to four years.
“We will be just fine … so don’t worry we won’t be able to pay it back,” Alexander told the commission. “It may not even be necessary, that’s my hope.”
The city will use $3.8 million of the county grant to purchase the property at 711 N. Orange Avenue. The remainder of the county grant will go toward refurbishing the theater, including expanding seating by 50%.
The future of the 23-year-old nonprofit theater was up in the air just a year ago when the owner of its building said its lease would end and the building would be sold. That left theater supporters scrambling for a new home until, ultimately, the city agreed to buy the property through the grant.
As part of the agreements, the playhouse will be required to provide a report on its performance metrics each year to the city.
City seeks developer for Seven Oaks Park
Tired of seeing little use of Seven Oaks Park, which opened in January, the city is inviting developers to submit ideas to build out a pad within the park that would potentially draw more people to the greenspace. (Red outline in above photo at top of page.)
Permitted concepts could include “bars, taverns, and cocktail lounges (with at least 51% of revenue derived from food sales); bicycle shops; breweries and distilleries (with food service); corner stores (excluding convenience stores); fine arts museums; instruction in fine arts, dance, and music; food halls; health and wellness studios; recreational facilities; restaurants (including fast-casual and fine dining); retail businesses; specialty food and beverage markets; and theaters for film, music, or performing arts.”
The city won’t be obligated to accept any of the ideas, but can use the “invitation to negotiate” as way to feel out interest in the project, City Manager Randy Knight said.
“The city expects this redevelopment will respect and grow the quality of the city’s unique attributes and special features of Winter Park while remaining relevant to today’s social gathering places like Foxtail Coffee Co. and Shady Park in Winter Park, Plant Street Market/Brewery in Winter Garden, East End Market in Orlando, and Boxi Park in Lake Nona,” the document reads.
Mayor Sheila DeCiccio said the neighbors and other businesses “desperately” want something to happen there.
Commissioner Craig Russell agreed, saying that despite the controversy related to the park, “I think the spirit of this park was deliberately designed for this process … it was what the plan was and I think it’s time.”
Commissioner Warren Lindsey suggested a shaded area might be a good component of whatever development plans take shape considering the Florida heat the years it will take for the park’s oaks to mature.
New limits on residential pickleball
Residents who are looking to build a pickleball court on their property will find it hard, or maybe impossible, to do so under new rules imposed by the City Commission.
The rules, which are designed to prevent noise complaints related to the game’s trademark near-constant ball whacks, will not affect commercial or public pickleball courts.
Planning Director Allison McGillis estimated there are fewer than five residential courts in the city, though some homeowners may seek to convert tennis courts to pickleball over time.
“I don’t foresee a lot of them popping up, but it’s becoming more popular,” she said.
McGillis proposed changing city code to require pickleball courts have 20-foot setbacks from the rear and side property lines, an increase from the required 10 feet for tennis courts.
But commissioners opted to increase the requirement to 150 feet, meaning new courts would be virtually impossible for now given the size of most lots.
One private pickleball court is expected to be built just off Park Avenue and Morse Boulevard as part of a private residence attached to a coffee shop. But that court would not be impacted by the new rules because of a special variance given to the project.
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by Beth Kassab | Aug 12, 2025 | Arts and Culture, News
Parade of Bands canceled for second year
The future of the Pop-Tart Bowl tradition that brought crowds to Winter Park is still uncertain
Aug. 12, 2025
By Gabrielle Russon
Paul Canchester, a retiree from the Chicago suburbs, has brought his family to Winter Park to watch the Parade of Bands for years as part of their annual Orlando vacation. The memories started when his kids, now adults, were young.
He described the anticipation waiting for the two university bands in town for the Pop-Tart Bowl shutting down the entire Winter Park downtown to play for free to the big crowd.
“Goodness, it was such excitement,” Canchester said. “We got a seat along Park Avenue and you could hear them playing before you could see them. You knew they were coming because you could hear the music a block or two away. And then it gradually got louder and louder, and then they came around the corner, and there they were, lined up with their uniforms on and playing their music. It was fantastic.”
Canchester said he is disappointed and fears it might not return after the city confirmed to Winter Park Voice that the parade is canceled for the second year in a row.
“The residents love it. The tourists love it,” Canchester said. “I hope they can find a time for the bands to play.”
Similar to last year, the parade is a casualty because of the game’s timing in the evolving college football playoffs.
One city official expressed hope the parade might return in 2026 or 2027 and said the Winter Park will always be a happy Parade of Bands host — whenever that may be.
The game’s weekend afternoon start time – 3:30 p.m., Dec. 27 – makes it logistically impossible to transport the bands to Winter Park for the parade, feed them lunch and then send them off for their other responsibilities for the bowl game, Miller said.
“It just makes it a really tight schedule,” said Johnny Miller, Winter Park’s special events manager, adding the kickoff time is decided by the TV networks. “It’s not in our control or the Pop-Tart Bowl’s control. … Sometimes the lower tier bowls, they get what they get.”
Already, Miller’s phone is ringing as people wonder about the parade’s status even though it’s too early to know which teams are playing in the game.
Somebody even called Winter Park last year, inquiring if another city could poach the parade.
“I don’t want them to think Winter Park doesn’t want to do it,” Miller said.
The Parade of Bands became an annual tradition dating back to 2007 and easily drew at least 2,000 or more — especially if a Florida team was playing in Camping World Stadium.
College football underwent a major change when it expanded to a 12-team playoff bracket in the 2024-25 season. There is talk of more bowl games getting added to the playoffs which could potentially shake up the Pop-Tart Bowl so it ends up in a more high-profile, later time slot to bring back the parade, Miller said.
Miller said it’s unclear the timeline for the proposed playoff expansion.
“It could happen next year. It may be two more years,” Miller said. “Nobody knows.”
But he added the city will welcome back the Parade of Bands as soon as it can.
“It’ll always have a home here,” Miller said.
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Gabrielle Russon is a freelance reporter and former reporter for the Orlando Sentinel, where she covered K-12 education, colleges and universities and the tourism industry. She lives in Orlando with her family and writes about politics, education, theme parks and the courts.
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by Beth Kassab | Aug 12, 2025 | Arts and Culture, City Commission, News
Winter Park gives main character energy in 'Happy Wife'
The authors explain how the city and a number of local haunts became a lavish — and sometimes dark — setting for the novel featured by Jenna Bush on the Today Show
Aug. 12, 2025
By Beth Kassab
Kendall Shores writes about Winter Park like a local because she is one.
Her parents met at Rollins College and married in Knowles Memorial Chapel. She attended Park Maitland, Trinity Preparatory and Winter Park High, where she rowed crew.
She’s seen the glitter of Park Avenue and the dirt swept under the rugs in the old-guard historic homes and the ultra modern mansions that surround the central district.
So when Shores talked to co-author Meredith Lavender about a setting for their debut novel “Happy Wife” she felt called to draw on her personal experience.
“I said, ‘Look, I know everyone thinks their hometown is interesting, but hear me out,'” Shores recalled. “… I think we understand that readers really enjoy a strong sense of place. And Winter Park, when you are there, has a strong sense of place.”
Cue the applause from the urban planners and preservationists.
‘Happy Wife’ throttled to the buzzsphere after the Today Show’s Jenna Bush featured it last month and called it a “delicious, fun summer” read.
City Commissioner Warren Lindsey then passed out copies at the next City Hall meeting and declared the mention not only a worthwhile book rec, but also a little atonement for the Today Show’s recent snub of Winter Park.
Not a word about the city was spoken during multiple unrelated segments filmed at Central Park for the Today Show’s third hour, which only promoted neighboring Orlando. The May appearances, coordinated by Visit Orlando, prompted Mayor Sheila DeCiccio to question the city’s future cooperation and waiver of park rental fees with the taxpayer-funded tourism marketing agency.
“They made up for it,” Lindsey said. “And we have to be able to make fun of ourselves a little bit.”
Is it any wonder the city lends itself so well to fiction?
The book is filled with local references from Interlachen Country Club to Fiddler’s Green Irish Pub and the condominium Enron’s Kenneth Lay called home when he was still with Florida Gas Co.
“Do you not like living here?” the main character, Nora, a 28-year-old whose marriage is at the center of the thriller, asks a friend.
“I like tax breaks. I like boat rides and sunsets on the lake and summer all year. But people like Autumn act like this place is $%&ing Paris or something. It’s Florida, not the %&* center of the universe.”
“You’re spicy this morning. Who hurt you? Did someone at the party try to tell you the Morse Museum is better than the MoMA again?”
Lavender and Shores, who both live in Atlanta, say they’ve heard talk of people wondering if any of the characters are based on specific individuals, but they aren’t.
All of the characters formed organically as the authors said they explored the dangers of “romanticizing your life, your partner or even your community too much” through a mystery with a number of turns.
Lavender, a television writer whose credits include “Nashville,” grew up on the north shore of Chicago and hadn’t spent much time in Central Florida.
Now, though, she’s had a proper introduction to Winter Park via Shores including, of course, the Scenic Boat Tour.
“People really have Florida in their minds as one thing and, for me, it had touches of Wisconsin and lake country and I loved that,” she said.
The co-authors expect to be in town again soon for events related to the book. Stay tuned for dates.
And there’s already another story in the works that builds on the last.
Winter Park, Shores said, continues to be the “anchor.”
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by Beth Kassab | Aug 5, 2025 | City Commission, News, Taxes, Uncategorized
Winter Park to keep property tax rate the same for 18th year
The city’s $233.5 million budget accounts for 7% growth in property tax revenue based on higher values as well as increases in utility fees
Aug. 5, 2025
By Beth Kassab
Winter Park City Commissioners will keep property tax rates the same for the 18th year in a row despite pressure from two commissioners to consider increases.
With a 3-2 vote to hold the line at the July 23 City Commission meeting, officials signaled that the increase in property values will drive a 7% increase in property tax revenues — from $36.2 million to $38.9 million — will be enough to cover expenses along with significant proposed increases in utility rates.
The city’s overall budget is proposed to increase by 8.9% or $19 million to $233.5 million.
City Manager Randy Knight cautioned that its likely he will ask commissioners to raise the property tax rate next year on top of the utility increases that are being proposed this year.
Mayor Sheila DeCiccio along with commissioners Warren Lindsey and Kris Cruzada voted to keep the millage rate the same. Commissioners Marty Sullivan and Craig Russell dissented.
Sullivan began talking about a potential increase months ago in a letter to residents, citing growing costs and changing economic conditions. He said he wanted to raise the millage rate by a quarter mil with the intent of revising it back down in September after receiving reassurance from the city’s share of revenue from the state sales tax and other sources wouldn’t plummet.
“That’s a big unknown,” he told the group, citing needs like a new fire training center and continuing to build the city’s reserve fund, which would prove crucial in the event of a major hurricane or other disaster.
Russell surprised some observers by going even further, proposing a half mil increase.
He was elected as a first-time candidate in 2024 and was championed by local business interests and even campaigned on cutting taxes and targeting waste.
But he said he’s learned a lot about what it takes to keep the city running with the high level of service that residents have come to expect.
“How long can we provide the level of service we do without addressing that taboo subject?” he asked.
He proposed earmarking any increase for specific needs like roads or sidewalks to provide residents with “transparency” about how the dollars will be spent.
Russell said he knows most elected officials shy away from raising taxes because it could cost them their jobs the next time voters got to the polls.
“Anybody sitting up here is afraid of not getting elected the next time,” he said. “I’m a liar …” he said referring to his own campaign materials last year that called for reducing taxes. “But when you dive into it and sit here and you take on fiscal responsibility for thousands of people you have the ability to learn what that really means.”
The seats belonging to Sullivan and Russell are up for election next year.
DeCiccio expressed some doubt about how much longer the city would be able to maintain property tax rates, even with higher appraised values. She attributed the city’s growing values to the level of service residents receive when it comes to quick police and fire response, parks, roads, electricity and other services the city provides.
“The level of service and higher property values go hand in hand,” she said. “It truly amazes me that we are able to maintain the same millage rate and still maintain that … I don’t know how long we will be able to do it, but we can definitely do it this year, make this the 18th year we don’t raise property taxes.”
Residents will, however, see other proposed changes that are likely to hit their wallets.
The average resident will pay an extra $23 for electricity, water and stormwater is the proposed changes are approved.
The next budget hearing will take place next week on Aug. 13 where residents can sign up to speak on the budget.
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