Central Florida Events
Real events, real dates — across Ocoee, Winter Garden, Winter Park, St. Cloud, Lake Nona, Orlando & beyond.
Town
Date
Category
Event Sources — Updated Weekly
Always verify event details before attending. Dates, times, and locations may change. Each card links directly to the official source. Want to add an event? Submit it here.
Showing 18 events matching “Winter Garden”(sorted by date)
Winter Garden Shop, Dine & Stroll — MAY-nia
Annual MAY-nia community day in historic downtown Winter Garden. Shop local boutiques and earn raffle tickets. Live music at Centennial Plaza: Sammy Velez (11 AM–2:30 PM) and Earthtonez Music Collective (3:30–7 PM). First 20 shoppers at each store get a free tote bag.
Horizon West Block Party — Flamingo Crossings
Monthly Horizon West Block Party at Flamingo Crossings Town Center. Live DJ, food trucks, face painting, balloon artists, and a community scavenger hunt. Family-friendly and free to attend. Bring the whole family!
Mother's Day Farmers Market & Kids' Craft
Special Mother's Day edition of the Winter Garden Farmers Market. In addition to 100+ regular vendors, kids can participate in a free Mother's Day Card Craft activity. A perfect morning outing for the whole family. Contact: farmersmarket@downtownwg.com | (407) 656-4111. Free admission.
Winter Garden Memorial Day Ceremony
Annual Memorial Day ceremony at Veterans Memorial Park co-presented by the City of Winter Garden and American Legion Post #63. Roll Call of Veterans, formal wreath placement, and patriotic songs. Free and open to the public.
Fridays on the Plaza — May Series (Winter Garden)
Free weekly outdoor concert series every Friday in May at Centennial Plaza Gazebo in historic downtown Winter Garden. May lineup: May 1 — PhoeNyx (Pop) · May 8 — The Danny Alan Trio (Top 40) · May 15 — Scott Davidson (Rock) · May 22 — Molly M (Pop/Top 40) · May 29 — Gentleman of Jazz. Bring a lawn chair. Free admission.
Fridays on the Plaza — Salted Vine Band
Weekly free outdoor concert series at Centennial Plaza Gazebo in historic downtown Winter Garden. June 5 features the Salted Vine Band playing classic rock. Bring a lawn chair. Free admission.
Winter Garden Farmers Market 18th Birthday Party
The beloved Winter Garden Farmers Market celebrates its 18th birthday! Special festivities include a DJ, face painting, and snow cones alongside the regular 100+ vendors. Contact: farmersmarket@downtownwg.com | (407) 656-4111. Every Saturday, rain or shine. Free admission, pet-friendly.
$5 Summer Flix — Zootopia 2 & Spaceballs
Garden Theatre's Summer Flix series returns with double features for just $5! Morning show: Zootopia 2 (PG) at 10 AM. Afternoon show: Spaceballs at 2 PM. Tickets available online only. Cashless venue. Free parking in downtown Winter Garden.
Fridays on the Plaza — Lynne Gibson
Weekly free outdoor concert series at Centennial Plaza Gazebo. June 12 features Lynne Gibson performing classic rock. Bring a lawn chair and enjoy the evening in historic downtown Winter Garden. Free admission.
Fridays on the Plaza — Theo Moon Music
Weekly free outdoor concert series at Centennial Plaza Gazebo. June 19 features Theo Moon Music performing acoustic sets. Bring a lawn chair and enjoy the evening in historic downtown Winter Garden. Free admission.
Fridays on the Plaza — Francesca Tarantino
Weekly free outdoor concert series at Centennial Plaza Gazebo. June 26 features Francesca Tarantino performing acoustic sets. Bring a lawn chair and enjoy the evening in historic downtown Winter Garden. Free admission.
Summer Flix at the Garden — $5 Movie Nights
Summer Flix at the Garden Theatre — $5 family-friendly movie screenings throughout June. A beloved Winter Garden summer tradition. Check gardentheatre.org for the full schedule and film lineup.
Winter Garden Party in the Park — 4th of July
Annual 4th of July Party in the Park at Newton Park. Live entertainment, food vendors, and family activities starting at 6 PM. Professional fireworks display at 9:15 PM. Free admission.
Winter Garden All American Kids Parade
22nd Annual All American Kids Parade hosted by the Winter Garden Masonic Lodge. Children decorate bikes, wagons, and scooters for a patriotic parade through historic downtown Winter Garden. Free family fun on Independence Day morning.
Dog Days of Summer — Launch PAW-ty
Opening night of the Dog Days of Summer art exhibit at Winter Garden City Hall. Community members are invited to bring their dogs to this "Ulti-MUTT" art exhibit launch party. Free to attend.
Fridays on the Plaza — Live Music Series
Free weekly outdoor concert series every Friday evening at Centennial Plaza Gazebo in historic downtown Winter Garden. Rotating local and regional artists. Bring a lawn chair. Free admission.
Winter Garden Farmers Market
One of Central Florida's most beloved weekly markets at the Downtown Pavilion. 100+ vendors selling local produce, baked goods, artisan crafts, and live music from 9 AM–1 PM. Every Saturday, rain or shine. Contact: farmersmarket@downtownwg.com | (407) 656-4111. Free admission, pet-friendly.
Homegrown Market at Hamlin
Bi-monthly open-air community market at Home State Brewing Co. in Hamlin Town Center. Local artisans, fresh food vendors, live music, and community vibes. 1st Sunday features Cars & Coffee. Dog-friendly (leashed). Free admission. Vendor info: Horizon West Happenings Vendor Portal.
Feature Your Event
Get your event in front of thousands of Central Florida locals. Featured events appear at the top of the page with a prominent spotlight card.
Missing an event in your town?
Help us keep Central Florida informed — submit your event and we'll review it for listing.
Submit an Event