Downtown Winter Garden News

Check here for the latest news, happenings, and announcements. There is always something new and exciting in Downtown Winter Garden!

Shop, Dine & Stroll with Live Music & Raffle “May”nia

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

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

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

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

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 […]

It is No Trick, Winter Garden Celebrates Halloween for 12 Days

It is no “trick” that Halloween is celebrated for 12 straight days in Winter Garden. Rather, it is a “treat” for the community to enjoy our historic downtown masked with spooky and fall-themed décor, along with activities and entertainment. Hosted by the City of Winter Garden, Halloween Experience 2023 (October 20-31) provides FREE family-friendly festivities, […]

Downtown Winter Garden to Host Summer Sidewalk Sale

The shops of historic downtown Winter Garden will host a Summer Sidewalk Sale on Saturday, August 26, 2023. Stroll the scenic streets to discover boutique bargains while enjoying the small town charm. The daylong sale is a great time to find deals on those one-of-a kind items that can only be found at downtown’s specialty […]

Winter Garden Hosts Nostalgic Fourth of July Events

Winter Garden is celebrating America’s birthday in a big way with several free community events. In addition to the Red, White & Blue Americana festivities, historic downtown is adorned in patriotic colors making it a nostalgic backdrop to stroll, dine, shop, take photos, and kick back with family and friends. The small town charm mixed […]

Arts in April Events in Downtown Winter Garden

Celebrate Arts in April with a variety of community events for all ages to explore and create art in conjunction with World Art Day. From kids art sessions at the Winter Garden Farmers Market and Best of Show art exhibitions, to an Urban Sketchers competition, an Arts in April Light Show, and much more, there […]

Shop, Dine, & Stroll with Live Music in Historic Downtown

Spend the day visiting your favorite downtown shops and restaurants and discover some new ones at the daylong SHOP, DINE & STROLL event in scenic historic downtown Winter Garden on Saturday, March 25. The streets are abloom with spring flowers, providing a colorful backdrop for a stroll through the small town charm. In addition, live […]


* indicates required
I am a....