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Downtown Winter Garden News
Check here for the latest news, happenings, and announcements. There is always something new and exciting in Downtown Winter Garden!
Annual Summer Sidewalk Sale Combines Savings with Entertainment
July 2, 2025
Looking for something fun to do in downtown Winter Garden as the summer season comes to an end? Mark your calendar for Saturday, August 2, 2025, and experience one of the season’s most exciting events: the Annual Summer Sidewalk Sale! This all-day event offers the perfect mix of bargain shopping, family-friendly activities, live music, and […]
Summer Flix at the Garden
June 4, 2025
Enjoy your favorite FLIX for $5.00 TIX all summer long at the iconic Garden Theatre on Plant! The City of Winter Garden is hosting a summer movie series with budget-friendly ticket prices and concessions that provide a fun school break outing for all. The line up of kids’ matinees include timeless animated features plus FREE […]
Fourth of July Community Events Provide Nostalgic Fun
May 28, 2025
Winter Garden is the place to celebrate Fourth of July with a variety of down-home events reminiscent of the simple days of the past while providing the opportunity to create new memories of today. In addition, historic downtown Winter Garden is decked out in red, white, and blue providing a patriotic setting for gatherings with […]
Celebrate this Juneteenth at Charlie Mae Wilder Park
May 21, 2025
Looking for plans to celebrate this upcoming Juneteenth? The City of Winter Garden has you covered! Celebrate and commemorate this holiday with your friends and family at the 2025 Juneteenth Community Celebration. Take time to reflect with your loved ones while enjoying live music, family-friendly activities, community resource booths, as well as a variety of […]
Shop, Dine & Stroll Raffle MAY-nia with Live Music
March 28, 2025
Downtown Winter Garden’s annual SHOP, DINE & STROLL returns on Saturday, May 3 — and this year, the rewards for shopping local are bigger than ever! Enjoy a day of browsing charming boutiques, savoring delicious eats, and soaking up live music as spring blooms line the streets. Plus, with chances to win exciting prizes in […]
30+ Acts Headline 2025 Winter Garden Music Festival
January 15, 2025
A look-forward-to event located in the heart of Downtown Winter Garden that is like no other! The City of Winter Garden presents their annual Winter Garden Music Festival, a FREE multi-stage, mega outdoor concert featuring a variety of talented, toe-tapping live entertainment and music genres. This 11-hour event includes continuous and simultaneous musical performances throughout […]
Winter Garden Hosts Dr. Martin Luther King, Jr. Community Celebration 2025
January 13, 2025
Celebrate with us as we honor and commemorate the life and legacy of civil rights legend, Dr. Martin Luther King, Jr. Hosted by the City of Winter Garden, the Martin Luther King, Jr. Community Celebration will be held on Monday, January 20, 11:00 a.m. – 4:00 p.m. The free community event includes a parade through […]
Downtown is Merry & Bright
November 26, 2024
When you combine the small-town charm of historic downtown Winter Garden with its festive decorations, you get the quaintest holiday wonderland that’s fitting for a Hallmark movie. Besides the merry ambiance, downtown events throughout December are sure to create merry experiences to make the holiday season extra special.
Show Your Love for Local at Downtown Small Business Saturday Sidewalk Sale
November 5, 2024
Get ahead of your holiday shopping this year while also supporting small businesses at our annual Downtown Winter Garden Small Business Saturday Sidewalk Sale on November 30th. The festive atmosphere, including holiday decorated streets and live music, makes this a fun outing for all during the holiday weekend. Get an early start and grab some […]
Downtown Transforms into a Two-Week Halloween Experience
September 24, 2024
Winter Garden provides the best treat for Halloween – a 14-day celebration in its historic downtown with free, fun, frightening, family-friendly festivities for the community. Hosted by the City of Winter Garden, Halloween Experience 2024 (October 18 – 31) features a daily hay maze, seasonal-themed photo locations, spooky and seasonal decorations, as well as seven […]