by Beth Kassab | Dec 11, 2025 | City Commission, News, Zoning and Development
Up to Eight Billboards in Winter Park to be Removed
The concept of a deal approved by the City Commission calls for four new billboards along I-4 while eight billboards along surface roads come down
Dec. 11, 2025
By Beth Kassab
For years, Winter Park officials have wanted to rid the city of billboards — considered by some to be analog roadside spam — and this week brought the first step in taking down as many as two billboards on Fairbanks Avenue, four of the structures on Aloma Avenue, one on Lee Road and one on Interstate 4.
City commissioners voted 5-0 to approve the concept of a deal that will require a series of land swaps and annexations and the permitting of four new billboards along I-4 in exchange for the eight other signs coming own.
“We’ve been working for many, many many years to try to eliminate as many billboards in the core of the city,” City Manager Randy Knight told the commission.
The terms call for:
- Clear Channel Outdoor will remove two billboards at 1873 and 2095 Fairbanks Avenue and one at 2522 Aloma Avenue. All three of those signs are double-sided. In exchange, Winter Park will issue a permit for Clear Channel to construct a new billboard at 2600 W. Fairbanks with a digital sign facing westbound I-4 traffic and a static sign facing eastbound traffic. Clear Channel would also remove a three-sided billboard at the southeast corner of I-4 and Lee Road. It would be replaced by a new billboard about 300 feet to the south, which will require a property swap with the city. The property swap could come before the commission as early as January.
- The Lamar Company will remove a digital billboard at 1621 Lee Road and the city will permit a new digital billboard at 909 N. Wymore Road. This means the city will also need to annex a portion of land for the structure.
- Outfront Media will remove three billboards at 2090, 2145 and 2431 Aloma Avenue. The city will issue a permit for a new digital billboard at 1885 Dartmouth Avenue. The city must annex several properties on Dartmouth to make that portion of the deal happen.
Mayor Sheila DeCiccio asked if Clear Channel could also remove a billboard on U.S. 17-92 and Gay Road. The company would not agree to remove it but said it would replace the digital side of that billboard with a newer technology that creates less light pollution.
“We definitely want that,” DeCiccio said of the upgraded features.
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by Beth Kassab | Dec 8, 2025 | City Commission, Election, News
Unopposed Races Seal Seats for Craig Russell and Elizabeth Ingram, Canceling Winter Park’s March Vote
The Winter Park High School coach will get a second term and a political newcomer will join the commission in March
Dec. 8, 2025
By Beth Kassab
Two City Commissioners were elected without opposition on Monday after the qualifying period ended at noon with only one candidate filing for each of the two seats that would have appeared on Winter Park’s March ballot.
City Commissioner Craig Russell was re-elected to his first full term in Seat 2 after winning a tight race in 2024 to finish the term vacated by Sheila DeCiccio when she became mayor. First-time candidate Elizabeth Ingram was elected to fill Seat 1, which was an open seat after Commissioner Marty Sullivan chose not to run again.
Elizabeth Ingram. Above photo: Ingram talks with a supporter at a recent event. Photos courtesy of the Ingram campaign.
Ingram, 38, will become the youngest member of the five-person commission.
A trained opera singer, she serves on the Public Art Advisory Board and previously led the Dommerich Elementary PTA. She said she hopes to focus on protecting the character that sets Winter Park apart from other communities.
She has been campaigning since the summer and filed to run in July.
“I’m so, so thankful for all of the supporters who rallied around me from the beginning,” Ingram said Monday afternoon, shortly after learning she would be elected without an opponent. “The most important thing for me as a commissioner is just being there for the residents. Am I representing them as well and as accurately as I can? Because that’s truly what my job is about. I’m excited to be a new young voice for Winter Park, and I’m excited to represent everybody.”
She raised just under $13,000, according to the most recent campaign finance report.
Michael Carolan, chairman of the real estate department at Winderweedle, Haines, Ward & Woodman, told the Voice in September that he planned to run for Seat 1 with backing from the Winter Park Chamber of Commerce. But Carolan announced on Facebook last month that he had decided not to run.
Russell said Monday that he is thrilled to have the opportunity to serve another term.
The Winter Park High School teacher and coach made history nearly two years ago as the first Black candidate elected in the city in more than a century. At 45, he is the youngest current commissioner.
Craig Russell
“I’m excited to continue the work that I started,” Russell said. “And I’m excited to hopefully gain the trust and respect of those who didn’t vote for me, because I work for and speak for all the residents.”
He listed engaging young people, improving infrastructure and transportation, and boosting community volunteerism and civic involvement as priorities. He helped spearhead the formation of a youth advisory council as well as an educational series on the safety of e-bikes and e-scooters for kids.
He has not yet filed a campaign finance report because he just filed his initial campaign documents last month.
Unopposed contests—particularly in local races—aren’t unusual and may even be increasing. According to data from BallotReady, 61% of city contests across the country were unopposed last year, compared to 44% in 2020.
Craig Russell poses with students who came out to support him at a candidate forum in 2024.
Fewer candidates mean voters have fewer choices about who represents them at the level of government closest to home—the policymakers who decide police and fire budgets, set road and traffic priorities, and shape the community through decisions about development, parks and how much residents pay for electricity and clean water.
Because both Winter Park races drew only one candidate, the March city election is canceled, and Russell and Ingram will be sworn in that same month. Commissioner Warren Lindsey was also elected without opposition earlier this year to Seat 4, meaning three of the five members of the incoming commission did not face voters at the polls.
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by Beth Kassab | Nov 21, 2025 | Arts and Culture, Historic Preservation, News
A Century-Old Lifeline: Welbourne Preschool Endures Amid Loss of Black Landmarks
As change continues on Winter Park’s west side, a preschool that opened in 1927 continues to provide a heartbeat for the neighborhood
Nov. 24, 2025
By Beth Kassab
On Sundays, you can find the Rev. Ronald Critton preaching at Bethel Baptist Church, one of Winter Park’s oldest historically Black sanctuaries.
But more than 65 years ago, Critton started out just steps across Welbourne Avenue from his pulpit as one of the tiny voices on the playground of the Welbourne Nursery and Preschool, once known as the Winter Park Day Nursery Association for Colored Children.
“I do recall the merry-go-round,” Critton told a group gathered recently at a celebration of Welbourne’s history and a fundraiser for its future. “Back then, being a young Black kid, we weren’t allowed to be in certain environments, and that was the only school for us … I felt that I was loved and cared for.”
The Rev. Ronald Critton speaks at an event for the Welbourne Preschool.
On Winter Park’s west side — where old homes and buildings disappear almost as quickly as parking spots along Park Avenue at Christmastime — the Welbourne has remained a beating heart of the historically Black neighborhood for nearly 100 years.
This year, Hannibal Square, founded in 1881 by free Black families who worked for the city’s wealthy white winter residents, lost the Gardens at DePugh Nursing Center.
The first licensed facility for Black seniors, dating back to 1956, announced in September that it would close — the latest in a wave of redevelopment over the last two decades as land values have soared.
But the Welbourne, which opened in 1927, continues to buck the odds.
Artwork from Welbourne students was displayed at the event.
Executive Director Latonya Pelt said the school’s mission is too important to let go. She is grateful for a group of loyal supporters, including alumni like Critton, who have helped raise about $70,000 toward the school’s $100,000 goal. Local business leaders such as Gary Lambert of Gary Lambert Salon on Park Avenue and Rick Baldwin, founder of Baldwin-Fairchild Funeral Homes and Cemeteries and now operator of Baldwin Brothers Funeral & Cremation Society, were recognized among key supporters at the recent event.
“I tell our teachers all the time — we care beyond the classroom,” Pelt said. “We care if the children are hungry, if they need anything. We are all a village.”
A Welbourne student hands out pens to guests.
The Welbourne provides child care and preschool for free or on a sliding scale based on a family’s income. Full tuition for an infant is $315 per week and decreases to $170 per week for a 4-year-old.
The school currently serves 53 children, from infants to age 4 and is open Monday through Friday from 7 a.m. to 6 p.m.
The fundraising campaign helps provide reduced tuition for qualifying families and increase teacher salaries to reduce turnover. Payroll is the school’s biggest expense but also its greatest asset.
“It’s not a high-paying industry,” Pelt said. “We want to make sure we keep qualified teachers.”
Minnie Woodruff recounts her family’s story and her experience at the school.
Minnie Woodruff remembers one such teacher from when she attended Welbourne before graduating at age 4 in 1943.
Rick Baldwin talks with Mary Daniels, who once worked as a teacher at the school and later served as president of its board, and Mayor Sheila DeCiccio.
At the recent gathering, she recalled Mrs. Richardson, whom she described as “the teacher, the cook, and if you got sick she would blow your nose.”
Woodruff went on to attend Spelman College and graduate school and enjoyed a long career as an educator. She credits the preschool with helping lay a solid foundation for herself and her seven siblings in a segregated world.
That work continues today, though the school now draws families from a broader area than just Winter Park. Many parents choose Welbourne because they work in Winter Park or face long waiting lists for subsidized child care elsewhere.
“The average two-parent working family in the U.S. cannot afford high-quality childcare,” said Sharon Carnahan, who serves on Welbourne’s board of directors and recently retired from Rollins College as a psychology professor and executive director of the Hume House Child Development and Student Research Center.
Critton, the pastor at New Bethel, said he hopes more Welbourne graduates find their way back to supporting the school and the neighborhood, where he recently became a resident once again.
“It’s been full circle for me,” he said.
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by Beth Kassab | Nov 19, 2025 | Arts and Culture, News, Taxes
With Partner Gone, Blue Bamboo Works to Push Ahead on Arts Project in Old Library
The music venue received approval to keep $900,000 of its original grant from the Orange County Arts & Cultural Affairs Advisory Council
Nov. 19, 2025
By Beth Kassab
There are still plenty of questions about who or what will replace a key partner that walked away from the Blue Bamboo project to transform Winter Park’s old library into an arts hub.
In a memorandum to Orange County’s Arts & Cultural Affairs Advisory Council last week, Blue Bamboo’s new leader listed 10 arts nonprofits as “examples of prospective tenants.”
But none of the groups contacted by the Voice — from the Orlando Gay Chorus to Orlando Fringe, Central Florida Community Arts, and Rollins College — said they were in discussions to take on permanent space in the three-story building.
Founder Chris Cortez performs at the Blue Bamboo last month in his final concert there.
Jeff Flowers, a chemist and arts philanthropist who served two stints on the Maitland City Council, recently took over day-to-day operations of the music venue after founder Chris Cortez was diagnosed with brain cancer and stepped away.
“I’m holding my nose above water,” he said of the many aspects of the project he has had to pick up on short notice.
Flowers said he is in talks with a couple of potential tenants but declined to name them. He has not yet reached out to the organizations listed as examples in the memorandum he provided to the advisory council when he won approval last week to retain most of the $1 million grant awarded to the original project last year.
Under revised terms, the new grant amount is $900,000 and will likely be disbursed in two payments, he said, after the project reaches certain milestones and provides documentation for construction and other expenses.
Central Florida Vocal Arts, which stages a variety of musicals and operas, was originally slated to occupy the second floor and help Blue Bamboo pay the rent on the building as well as raise the $500,000 in matching funds required by the grant, which comes from the Tourist Development Tax collected on hotel rooms in Orange County.
CFVA withdrew from the project after Executive Director Theresa Smith-Levin said she was unable to reach a lease agreement with Blue Bamboo.
Blue Bamboo will now be responsible for raising $450,000 in matching funds under the new grant terms.
The organization currently pays the city $132,000 a year in rent for the building, an amount scheduled to rise to $276,000 next year.
Flowers said he hopes to secure tenants for the building along with shared spaces for costume design, lighting fabrication, recording suites, back-office support, and more. He added that he still has time to solidify those plans.
“Our revised leasing plan will allow a more diverse group of subleases to support the ongoing costs in our master lease, and the Shared Space plan will provide a new income stream that is responsive to the expressed needs of the community it serves. Finally, our capital campaign efforts will integrate Blue Bamboo into the local business community to ensure continued financial support,” Flowers wrote in the memo to the county.
Flowers is not only a longtime supporter of the venue and now its leader, but also the person who loaned Blue Bamboo money for the initial round of construction and other expenses needed to open this summer in the old library building.
He said he has loaned the project about $1 million so far.
“I’m going to make sure this project succeeds,” he said.
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by Beth Kassab | Nov 14, 2025 | County News, News, Taxes
Rosen Hotels Leader Calls for Tourist Transportation Tax to Boost SunRail, Lynx
Frank Santos, who lives in Winter Park, says out-of-state visitors would pay for the upgrades as an added tax on hotel bills
Nov. 14, 2025
By Beth Kassab
Frank Santos wanted to make SunRail work as his daily commute.
The chief executive officer of Rosen Hotels & Resorts had a lot in his favor. He lives just three blocks from the Winter Park station. On his morning walk to the train he often stopped at Croissant Gourmet on Morse Boulevard for coffee and, occasionally, a pastry.
He spent the ride to his office near International Drive reading the day’s news or getting work done — something impossible to do behind the wheel on Interstate 4.
Santos even devised a system for when he arrived at SunRail’s Sand Lake Road Station, the closest stop to his office overlooking the golf course at Rosen Shingle Creek. He left a car there Monday through Friday to cover the last 15 minutes or so of his trip.
But after about a year, he stopped taking SunRail.
“It was just complicated,” he said. He called his experiment with Central Florida’s underfunded and incomplete mass transit system largely worthwhile — even enjoyable at times — but one that underscored how the region is built around the door-to-door convenience of cars.
“I would do it again if I could get closer to my office,” he said.
Winter Park’s SunRail station is one of the commuter train system’s busiest.
It’s been about five years since he stopped his regular SunRail commute. Since then, he has helped guide his company, which operates seven hotels, through the COVID pandemic and, last year, the death of founder Harris Rosen.
But this week he found himself reflecting on those train rides and what he sees as untapped potential for Central Florida to finally build a mass transit system that works for more people.
Santos acknowledged that any inconvenience he experienced on SunRail, or the gridlock he faces routinely on I-4, is small compared to what some of his employees endure. Many Rosen Hotels workers and others who earn their livelihoods as restaurant servers, ride attendants, desk clerks, housekeepers, and groundskeepers rely on the Lynx bus system and spend hours on buses each day.
“We need our employees to get to work faster,” he said. “My employees take up to two hours to get to work.”
That’s why an idea he has tossed around since 1999 now has a name: the Tourist Transportation Tax.
It would be paid only by out-of-state tourists on their hotel bills, and the revenue would be used exclusively for transportation needs such as extending SunRail to Orlando International Airport and the Convention Center and, for the first time, providing a dedicated funding source for Lynx so it can add buses and increase route frequency.
The proposal is gaining interest across the state, including in Winter Park.
Winter Park Mayor Sheila DeCiccio said she shares many of the same goals: extending SunRail service to weekends, which could reduce traffic during major events such as the Winter Park Sidewalk Art Festival, and improving bus service.
Winter Park was SunRail’s second-busiest station last year with 124,000 riders, according to system statistics. Only the Lynx Central Station stop in downtown Orlando had more, with 138,000 passengers.
“We offered to pay for the train to run on the weekend and they wouldn’t do it,” DeCiccio said. “We want the train to run in and out of the airport. We want the buses to run better. Those are exactly the kinds of things I’ll be looking for in a plan.”
DeCiccio’s comments came after joining about 200 people who listened to Santos’ proposal — as well as a plan by Sen. Carlos Guillermo Smith, who wants to change how existing hotel-room tax dollars are spent — at an Orange County League of Women Voters luncheon this week.
The discussion turned tense at times, with Santos arguing that Guillermo Smith’s statements about the Lynx budget were misleading and stepping in to defend the tourism industry, which he noted already contributes heavily to roads, schools, parks, and other essential services as the top property taxpayers in Orange County.
Walt Disney Company, Universal Studios, Marriott Resorts, Hilton Hotels & Resorts, and SeaWorld regularly appear on the county’s Top 10 list of property taxpayers, according to the property appraiser’s records.
Guillermo Smith, an Orlando Democrat, was especially critical of the public dollars allocated to Visit Orlando for marketing hotels and attractions. The quasi-public tourism bureau was the subject of a recent county audit that questioned its expenditures.
Sen. Carlos Guillermo Smith. Frank Santos pictured at top of page.
“I think $105 million in public money to Visit Orlando is an insane amount to give when we have so many community challenges,” he said. “We know that tourism is a huge economic driver in our region. … But we also have to acknowledge that tourists place a large strain on our community’s resources.”
Santos defended the spending.
“The senator doesn’t understand the cost of doing business,” he said. “We spend $40 million a year on sales and marketing at Rosen Hotels. Coming out of COVID, everyone understands the cost of doing business has increased.”
How much of the current 6% tax on hotel stays should be devoted to tourism marketing, the convention center, and other industry needs — versus helping local residents — has long been debated in Central Florida.
The difference this time is that someone from the tourism industry is proposing a new solution instead of simply guarding the existing 6%, which generated $385 million last year.
Santos still wants to protect that 6 cents on the dollar collected by hotels. But he wants to add another 1 to 4 cents dedicated to transportation.
Right now, he explained, guests pay 12.5% in taxes on hotel bills: 6% in Tourist Development Tax and 6.5% in sales tax.
Other popular destinations charge more. Chicago charges 17.3%. Austin charges 17%. New Orleans charges 16.2%. New York charges 14.75%.
“We could go as high as another four cents,” he said.
The steady revenue stream provided by the tax could be leveraged to finance major projects through bonds. One extra cent could generate nearly $350 million in bonding capacity, according to projections.
This table projects what different tax rates would generate each year and the capacity to bond against that revenue to fund projects. Source: Policy memorandum on Santos’ proposal
Importantly, hotels would exempt visitors with Florida driver’s licenses from paying the tax, meaning out-of-state visitors would fund the upgrades.
Santos needs the proposal to pass the Legislature and then win voter approval in a referendum. He says he has begun speaking with more tourism leaders to build support.
Without naming names, he said some organizations have encouraged him to continue pushing. At least one major group has suggested increasing the sales tax to fund transit — an idea backed by Orange County Mayor Jerry Demings that failed at the ballot in 2022.
Harris Rosen himself supported Santos’ plan before his death about a year ago, Santos said.
So he plans to keep talking, keep meeting, and keep spreading the word about the region’s needs.
One way he wants to do that is through another experiment. He plans to ride Lynx from a neighborhood where many workers live to his hotels on and near International Drive so he can better understand their challenges.
“I want to do it during the morning,” he said. “I plan to ride the bus from Pine Hills to my office.”
At the end of the day, he’ll face a familiar problem for any transit user in a car-centric region.
“And then I’ll find a way to get back home,” he said.
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