On August 11, snap and post a Selfie on social media to show your pride in Winter Garden. Snap a selfie at City Hall in Winter Garden located at 300 W Plant St. to show your Winter Garden pride on #CityHallSelfie Day on Tuesday, August 11, 2026. The annual online picture-sharing holiday is a fun way to express pride for your hometown and appreciation to local government service. Post your photo on social media with #CityHallSelfie and #wintergardenfl and then pop inside City

Come to downtown Winter Garden on July 4th to be a part of a grand 21-year-old tradition that brings the community together to celebrate America’s birthday. Winter Garden is the place to celebrate America's 250th Anniversary this 4th of July Weekend, featuring down-home events reminiscent of the simple days of the past while providing the opportunity to create new memories of today. Historic downtown Winter Garden is decked out in red, white, and blue, offering the perfect pa

DNA Productions has announced the 2026 - 2027 season lineup of their premiere season at the Garden Theatre on Plant in historic downtown Winter Garden. The Winter Garden City Commission approved a partnership with DNA Productions back in April to manage the Garden Theatre on Plant, and now in partnership with the City of Winter Garden, DNA Productions has announced the 2026 - 2027 season lineup of their premiere season at the Garden Theatre on Plant. The 2026 - 2027 lineup f

Enjoy family-friendly activities, entertainment, live music, community resource booths, food, and more. Join the City of Winter Garden for a Community Celebration in honor of Juneteenth on Saturday, June 20, 2026 from 10 am - 1 pm. Hosted by the City of Winter Garden, the celebration includes family-friendly activities, entertainment, community resource booths, a variety of food and merchandise for sale, and more! The Juneteenth Community Celebration takes place at Charlie Ma

Cheap movies are back in Winter Garden for the summer, with movies for everyone! Enjoy your favorite FLIX for $5 every Tuesday all summer long at the iconic Garden Theatre on Plant in downtown Winter Garden. From June 9 - August 4, 2026, this summer's Flix at the Garden features movies for everyone, with kids' matinees at 10 am and 2 pm, as well as evening screenings at 7 pm of classic and contemporary hits. Hosted by the City of Winter Garden, all tickets are $5.00 (no added

Popular Winter Garden booKshop, Writers Block Booksotre is having to close the location despite not wanting to leave the area. Independent bookstore, Writers Block Bookstore with locations in Winter Park and Winter Garden is having to close its Winter Garden store at the end of April thanks to their landlord choosing to terminate their lease to bring in a new tenant at a much higher rent. The bookstore which has been open in Winter Garden for five years, offers a curated sele

The popular Winter Garden music Festival returns to Historic Downtown Winter Garden. Brought to you by the City of Winter Garden, the Winter Garden Music Festival is a FREE multi-stage outdoor concert in historic downtown Winter Garden. This year's Winter Garden Music Festival 2026 takes place on Saturday, February 21, 2026 from 11 am - 10 pm, offering a variety of live entertainment and music genres performing continuously and simultaneously for 11 hours. The festival featur

See holiday classic movies for $5 in the timeless ambiance of the Garden Theatre on Plant. This holiday season, the City of Winter Garden is once again presenting Holiday Flix at the Garden featuring $5 Classic Holiday Movies. This years movies will take place on December 7, 9, 11, 14, 16, and 23, and includes National Lampoon’s Christmas Vacation, White Christmas, Gremlins, and more. These holiday classic movies will appeal to all ages and conjure past holiday memories, whil

Get ready for a jam packed December featuring Light Up Winter Garden. Winter Garden Christmas Parade, Winter Garden Christmas Golf Cart Parade, Holiday Night Market, A Merry Winter Garden Light Show, Main Street Holiday Stroll, and more! There truly is something magical about Downtown Winter Garden during the holiday season. At the center of it all is Centennial Plaza, where a large, fully decorated Christmas tree dazzles. This is where families gather, taking pictures, lift

Halloween Flix At The Garden takes over Garden Theatre on Plant this spooky season. The ambiance of the historic Garden Theatre in Winter Garden is the perfect setting to watch classic Halloween movies. Hosted by the City of Winter Garden, the spooky movie series features two family-friendly Halloween movies and one adult horror movie. Taking place on October 25 and November 1, 2025, this is the perfect way to celebrate spooky season in Winter Garden! Tickets to each movie is

The popular Winter Garden music Festival returns to Historic Downtown Winter Garden. The City of Winter Garden is once again hosting the...

The downtown Sidewalk Sale features participating stores with sidewalk sales racks, and more, so set a reminder to shop, support, and...