Kilts in January, Markets on Sundays: Winter Springs’ Year in Events
The Central Florida Scottish Highland Games fill Central Winds Park each January, the farmers market takes Trotwood on first and third Sundays, and December brings the parade to the Town Center. Winter Springs' calendar, explained.
3 minute read
Winter Springs does not do spectacle often, which is why its two great recurring spectacles land so well. Every January, its biggest park fills with kilts, cabers and pipe bands for one of the largest Scottish gatherings in the Southeast. And twice a month, on Sunday mornings, its neighborhood park turns into a farmers market that half the suburb seems to wander through before lunch. Add a December parade down the Town Center and you have the shape of the city’s year — quiet, park-based, and entirely its own. Here is the calendar that matters in Winter Springs.
January: the Central Florida Scottish Highland Games
The Central Florida Scottish Highland Games, organized by the Scottish-American Society of Central Florida, take over Central Winds Park each January for two days of heavy athletics and Celtic culture. The 48th edition ran January 17–18, 2026, and organizers bill the Games as the largest community event in Seminole County — thousands of visitors on a municipal sports park, which tells you something about both the event and the park. The program is the full Highland canon: caber tossing and the other heavy events, Highland dancing competitions, bagpipe and drum bands, whisky tasting, Celtic artisans and food, clan tents, border collie herding demonstrations and a non-competitive Kids Games version of the athletics for children. Practical notes from the regulars: gates open in the morning, admission is charged at the gate with advance tickets cheaper, parking fills across the park’s fields, and January in Winter Springs can mean anything from a crisp sixty degrees to full sun — dress in layers and treat the weather as part of the show. Our Central Winds Park guide covers the ground the Games take over.
First and third Sundays: the Trotwood farmers market
The Winter Springs Farmers Market runs on the first and third Sunday of every month at Trotwood Park, in the morning through early afternoon, organized by Specialty Pop Up Events, the Central Florida company behind a circuit of artisan and community markets. The market recently settled into the heart of the park, using Trotwood’s concrete walkways as its natural promenade — produce, baked goods, prepared foods, plants and makers, threaded between the playground and the pavilion so a market trip becomes a park morning whether you planned it that way or not. It is the most reliable recurring date on the city’s calendar and the easiest way for a visitor to see Winter Springs socializing with itself. Pair it with the splash pad and courts in our Trotwood Park guide, and note that market schedules shift around holidays — a quick check of the organizer’s listings before a special trip is the local habit.
December: Winter Wonderland at the Town Center
The city’s year closes where its civic life centers. Winter Wonderland brings the annual holiday parade and tree lighting to the Winter Springs Town Center, with live holiday performances by local performers and schools and the whole district turned into the town’s front room for an evening. In a suburb with no historic main street, the parade route through a purpose-built Town Center could feel like a substitute; in practice it feels like a tradition the town built for itself on purpose, which is more or less the story of Winter Springs in miniature. Our Town Center guide covers the district the parade runs through.
The supporting calendar
Around the three anchors, the city keeps a smaller rhythm: Food Truck Thursday evenings staged at Trotwood Park in season, with residents bringing chairs and blankets for dinner on the grass; city ceremonies at the Veterans Memorial at the Town Center; and the steady drumbeat of league seasons, tournaments and pavilion gatherings across the park system that never make a regional calendar but constitute most of local life. That is the honest summary of events in this suburb — three dates worth a drive, and a hundred worth living here for. Build a weekend around any of them with our Winter Springs guide, and find every venue on our Orlando Top Spots Map.
Best for: January visitors who want a festival with real scale, Sunday-morning market people, and anyone who believes a town’s character shows clearest at its recurring gatherings. In Winter Springs, it shows up in a kilt, carrying a caber.
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