Winter Park is synonymous with many things: unique cultural attractions, magnificent oak trees, charming (if bumpy) brick streets, spacious historic (and not-so-historic) homes, shimmering lakes connected by Venetian canals and a prestigious liberal arts college, among other very cool attributes.
But it’s also synonymous with weddings. Couples, regardless of where they live or plan to live, want to tie the proverbial knot here. That’s because—in addition to all the city’s other charms—it offers the most eclectic assortment of wedding venues imaginable.
From a soaring on-campus chapel to a rustic turn-of-the-century railroad depot and everything in between, there’s something for all aesthetics in the good old 32789. The only ceremony that usually can’t be accommodated is a spur-of-the-moment one—unless, of course, you’re willing to settle for City Hall. Some venues are booked a year or more in advance.
But you likely already know most of the venues (and you can check out a complete list in the accompanying directory that starts on page 78). That’s why this year we’re again going to focus on three entirely different—but equally joyous—ceremonies and the eclectic couples whom the nuptials celebrated.
Let’s meet Leland Hosto and Rachel Garber; Margaret Mitchell and Peter Duggan; and Erin Hunter Sills and Laurence Kuykendall—each of whom chose a different venue (and a different vibe) with the same happily-ever-after outcome in mind.
LELAND HOSTO & RACHEL GARBER
The Winter Park Racquet Club
Photographed by 28 North Photography
Leland Hosto liked country music; Rachel Garber liked rock ’n roll. He was a native of Nashville and listened to George Strait. She was a native of Winter Park and couldn’t get enough of post-
grunge rockers Creed. How could such a chasm be closed? Someone, clearly, needed to compromise.
Who really gave in? Well, in truth, both Leland and Rachel have come to appreciate one another’s music. At their wedding party, the band Blonde Ambition played Creed’s 1999 hit “Higher” as Leland and Rachel shared lead vocals, karaoke style.
The performance culminated with Leland crowd-surfing through the mosh pit. OK, so the Winter Park Racquet Club doesn’t technically have a mosh pit. But it might as well have had one that night. (In a genre change, Rachel’s father-daughter dance was to the strains of “My Wish” by Rascal Flatts.)
Then, on their honeymoon, the Hostos flew to California, where they traversed the Pacific Coast Highway from San Diego to San Francisco. The trip culminated with a concert by—you guessed it—Creed, who were (not coincidentally) performing in the Bay Area.
To Rachel, associate director for global partnerships for the Orlando Magic, Leland’s rock ’n’ roll conversion wasn’t even the most memorable aspect of the wedding. No. 1 on that hit parade of memories would be the reading aloud of their self-written vows. Leland, not normally an emotional sort, according to Rachel, actually teared up.
Those vows were, after all, a long time in the making. Leland and Rachel had been neighbors for years (their respective moms, she recalls, kept trying to play matchmaker). “We grew up near the Racquet Club,” she recalls. “So this was very sentimental for us. It almost felt surreal.”
The wedding was large—215 people attended—but the couple wanted it to feel like a casual, comfortable backyard party with an abundance of playful flourishes. They even set up a “merch tent” with such take-homes as ball caps emblazoned with HOSTO and T-shirts adorned with images of citrus and peacocks as a nod to Winter Park.
Before they formally tied the knot, Leland, a graduate of the University of Alabama, and Rachel, a graduate of the University of Georgia, had lived for six years in Miami, where she worked for the Miami Heat. (Leland, now purchasing manager for MRC Polymers based in Chicago, could work from anywhere.)
No disrespect to Miami—or to the Heat, bitter rivals of the Magic—but when an opportunity opened with the hometown team, both were eager to get back to Winter Park. “We love this place,” says Rachel. “I was born here. And Leland came to love it just as much as I do.” Sort of like how it happened with Creed.
The Team
Planner: Blue Ribbon Weddings (Katie Scully); ceremony: Winter Park Racquet Club; rehearsal dinner: AVA on Park Avenue; bridal gown: “Made With Love” from The Lovely (Miami); groom’s tuxedo: Menguin; hair and makeup: Makeover Station; jewelry: Be On Park (mother’s earrings and necklace); photographer and videographer: 28 North Photography, Chris Andrews Film; florals: Velvet & Twine; pastries: The Donut Bar; music: Blonde Ambition; officiant: Ron Krudo (cousin of the bride); goodbye brunch: Brick & Bowls.
LAURENCE KUYKENDALL & ERIN HUNTER SILLS
The Alfond Inn
Photography by Damon Tucci Photography
The eye-catching cake topper revealed some essential facts about Laurence Kuykendall and Erin Hunter Sills. It depicted a bride and groom along with four cats and one motorcycle. But the full story makes the esoteric symbolism of the design seem, well, understated.
Sure, the couple has four cats, which isn’t particularly remarkable. But Laurence is a former communications manager with BMW North America and marketing director at Ducati North America (a subsidiary of the Italian luxury motorcycle manufacturer). He recently retired from a similar role at Energica Motor Company, a manufacturer of electric motorcycles also based in Italy.
Erin, prior to her retirement from the corporate world, had enjoyed a storied career that included executive stints at Procter & Gamble, MMA (Marketing Management Analytics) and Facebook (now Meta), where she was director of global consumer insights.
And for the past two decades she has been a land-speed motorcycle racer who has become a 45-time world and national record holder in the sport. Her preferred ride is the BMW S1000 RR, which she has pushed to 242 mph on the Bonneville Salt Flats.
Among Erin’s many racing honors is being named the American Motorcyclist Association’s “Female Athlete of the Year” in 2014. The Smithsonian National Air and Space Museum in Washington, D.C., has one of her motorcycles and a riding kit displayed in its exhibition Nation of Speed.
Laurence and Erin own seven bikes between them—so they’re no weekend warriors; they’re motorcycle racing industry icons. Although they could have gotten married anywhere, Erin has family in Central Florida—including her 90-year-old mother, for whom she wanted the ceremony to be accessible. Says Erin: “She had a great time; we even decorated her wheelchair.”
This was the second marriage for both Laurence and Erin—their respective spouses had passed away—but the foursome had been longtime friends. (Erin’s late husband, Andy Sills, who died in 2015, was also a legendary land-speed racer.)
The wedding allowed plenty of time for socializing among the roughly 50 guests from around the country and the world who had converged upon Winter Park. There was, for example, a “girls’ dinner” the night before the ceremony at Bosphorous and an excursion for the guys to the Shooting Gallery in Orlando. A pool party was on tap for the following day at The Alfond.
Back home in San Francisco, Laurence and Erin continue their shared passion for motorcycling and Erin, at age 60, remains a competitive force in land-speed racing. An advocate for gender equity in the sport, she’s also co-founder of the online resource Women Riders Now.
The Team
Planner: Michele Butler Events (Sara Parkinson); ceremony: The Alfond Inn; rehearsal dinner: The Alfond Inn; pre-ceremony bridal dinner: Bosphorous; bridal gown: Grace Loves Lace (San Francisco); groom’s tuxedo: Robert Paul (San Francisco); hair and makeup: Maggie Dewine Hunter, niece of the bride, at MDH Beauty (Austin), About Face Design Team; photographer and videographer: Damon Tucci Photography, Jeffery Stoner Video; florals: Lee Forrest Design; cake: Sweet Miss V’s; music: Soundwave; officiant: Justin Hunter (nephew of the bride).
PETER DUGGAN & MARGARET (MAGGIE) MITCHELL
Knowles Memorial Chapel
Photography by Nat Puhr Photo + Cinema
After he graduated from the University of Buffalo in 2016 with a degree in marketing and finance, Peter Duggan wasted little time making his way south. He ended up in Atlanta, where he accepted a position as an account manager for Insight Global, a national staffing and services company.
He soon became infatuated on sight with a young woman at Insight Global who had passed him and a buddy on an escalator. He asked: “Who in the world is that?” Replied his buddy: “Oh, that’s Maggie; she’s new here, too.” Peter made it his mission to get as close as possible to this dark-eyed, dark-haired newbie.
“I think I told everybody in the company about it,” says Peter. “Except for her, at first.” Maggie was Margaret Mitchell, a native of Winter Park who had graduated from the University of Florida with a degree in public relations and snared a job in sales at the company. The two connected—“he made me laugh and kept me entertained,” says Maggie—and starting dating in 2019. They got engaged in 2023 and married in 2025.
There was no question where they would ultimately settle down, says Maggie, who adds that she “loved growing up in Winter Park; I loved the charm of this town.” Peter had no objection; the further south, the better, as far as he was concerned. “Winter Park reminded me of Savannah because of all the old oaks everywhere,” says Peter. “I thought it was beautiful.”
Maggie—who has a large extended family in town—wanted the couple’s 190 wedding guests to have an immersive Winter Park experience. They planned their ceremony for Knowles Memorial Chapel. Out-of-towners stayed at the Park Plaza Hotel while others stayed at The Alfond Inn. The rehearsal dinner was held at the Winter Park Farmers’ Market.
“We wanted the whole thing to be whimsical, eclectic, different, happy,” says Maggie. Celebratory events—including a reception under a large tent on a heavily treed lawn adjacent to her aunt and uncle’s home on Via Tuscany and an afterparty at Hannibal’s—incorporated some of their favorite music: The Grateful Dead (Peter) and Talking Heads (Maggie).
Collateral material—including signage—sported hand-drawn maps of the city’s landmarks and images of the couple’s beloved special-needs pet, Floyd (a French bulldog). The rehearsal dinner featured nods to Buffalo with an abundance of those oversized foam fingers saluting the NFL’s Bills.
Maggie, who was 9 months pregnant at press time, will continue to work for Insight Global from a home base in Winter Park. Peter has opened an office in Maitland that will become the Southeast branch of Intellicents, a financial-planning firm based in Minnesota.
The Team
Planner: Party Perfect (Debbie Mintzer); ceremony: Knowles Memorial Chapel; rehearsal dinner: Winter Park Farmers’ Market; pre-ceremony bridal luncheon: Hannibal’s; caterer and cake: Arthur’s Creative Events & Catering; bridal gown: Bridals by Lori (Atlanta), designed by Lazaro Perez; bridal luncheon dress: Bridal Finery; after-party dress, Sau Lee; bridal jewelry: Jennifer Behr (earrings); groom’s tuxedo: Indochino; groomsmen’s suits: Indochino; maid of honor dress: Markarian; bridemaids’ dresses: Significant Other; hair and makeup: Hair by Luis Marston-Vega, Lea Montes of LeaCakesMUA; photographer and videographer: Kristen Weaver Photography (bridal luncheon), Nat Puhr Photo + Cinema (ceremony); florals: Velvet & Twine; music: C’Energy Entertainment (wedding) Ella & The Bossa Beat (cocktail hour); officiant: Rev. Scott George (Belle Isle Community Church).