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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!
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 […]
Celebrate the End of Summer at the Annual Downtown Winter Garden Summer Sidewalk Sale
July 3, 2024
As summer winds down in downtown Winter Garden and residents and locals prepare for the fall season, the local mom-and-pop shops invite all to stroll the bustling sidewalks for sales, live music, and family fun. Our local shops always host unique treasures, from home goods, gifts, jewelry, clothing, home décor, and more. The warm sunshine […]
Celebrate the Fourth of July with festivities while exploring Downtown Winter Garden
June 12, 2024
Downtown Winter Garden’s July 4th festivities are nothing short of spectacular, offering a variety of activities for all ages. Whether you’re a resident or a visitor, the vibrant atmosphere and array of events make it a perfect place to celebrate America’s Independence Day. A Festive Parade + Breakfast to Kick Off the Day 20th ANNUAL […]
Shop, Dine & Stroll with Live Music & Raffle “May”nia
March 28, 2024
SHOP, DINE & STROLL on Saturday, May 4, is the perfect spring outing to relish the outdoors and flowering scenery while live music fills the air. It’s a chance to discover unique shopping and dining options and win great prizes in multiple raffles. The daylong event in historic downtown Winter Garden will be a fun […]
30+ Acts Headline 2024 Winter Garden Music Festival
January 16, 2024
Get ready for a day (and night) of music and fun at the Winter Garden Music Festival on Saturday, February 24, 2024. Presented by the City of Winter Garden, this mega outdoor concert provides 11 hours of continuous live entertainment throughout picturesque downtown. Admission is free so come out and enjoy! More than 30 top-notch […]
Winter Garden Hosts Dr. Martin Luther King, Jr. Community Celebration 2024
January 5, 2024
Join us at the annual Dr. Martin Luther King Jr. Community Celebration to commemorate the life and legacy of this civil rights legend. Hosted by the City of Winter Garden, the free celebration on Monday, January 15, 2024, 11 a.m. – 4 p.m., includes a parade through historic downtown, live entertainment, children’s activities, and more! […]
A Holiday Wonderland Awaits in Historic Downtown
November 16, 2023
Enter a holiday wonderland as festive decorations and light displays adorn historic downtown Winter Garden, embellishing its small-town charm. Courtesy of the City of Winter Garden, visit December 1, 2023, – January 7, 2024, to enjoy the sights and sounds of the season along with a variety of holiday events and plenty of unique shopping […]
Outdoor Holiday Market with Festive Entertainment
November 1, 2023
Experience a traditional outdoor Holiday Market right in historic downtown Winter Garden with festive shopping and merry entertainment for all ages. The pedestrian-only market takes place on Saturday, December 2, from 1 p.m. to 4 p.m., in the heart of a festive wonderland. With the streets closed, wander freely from booth-to-booth to shop for everything […]