Downtown Winter Garden News

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


Holiday Boutique Stroll, Holiday Carolers and SOBO’s Opening Reception

The second annual Holiday Boutique Stroll will be held this Thursday, December 10th from 10 am until 8 pm. This event is part of the Love Local program and will be the last event for the year. Stroll the outdoor sidewalk sale in Downtown Winter Garden to find that perfect holiday gift for that special someone. […]

Clock Tower ready for Christmas

Tis the Season to Make Memories

The small-town charm of downtown Winter Garden is even more pronounced during the holiday season when its historic streets become adorned with festive decorations and a line-up of outdoor seasonal activities that will delight all ages. From spectacular animated light shows, horse drawn carriage tours, carolers, a holiday mural wall, photo vignette locations, and seasonal […]

Christmas in Winter Garden Horse Drawn Carriage

2020 Downtown Winter Garden Holiday Guide

Downtown Winter Garden is a magical place during the holiday season, tons of events and beautiful sights. We’ve put together a guide so you don’t miss a thing. You can download and share our 2020 holiday guide by clicking on the button below! You can also find our event calendar here!

Downtown to Host Sidewalk Sale for Small Business Saturday

The nationally observed Small Business Saturday holds even greater importance this year, as local businesses need the support of their community more than ever. Consumers are urged to think small to help big this Saturday, November 28, to preserve the mom-and-pop businesses that are the heart of Winter Garden’s charm. Combine gift shopping with making […]

Books for Sale at Writer's Block Bookstore

Writer’s Block Bookstore Opens in Downtown

It is official — Winter Garden has a bookstore! Writer’s Block Bookstore opens their doors on November 20 in Downtown Winter Garden. The opening is perfect timing for holiday shopping with its wide selection of holiday-related books and gift items. Located at 32 W. Plant Street, the 1,500 square-foot full-service independent bookstore specializes in new […]

Vegetables from the Farmers Market

Local Farmers bring their Harvest to Winter Garden

There will be an abundance of local fresh produce at the market starting in late October when the fall crops start coming in and farmers begin their fall harvest.  The Winter Garden Farmers Market has the largest selection of local produce in Central Florida. We are fortunate to work with a group of amazing farmers.  […]

Garden Theatre Presents Matilda the Musical

The historic Garden Theatre in downtown Winter Garden is excited to present Matilda the Musical during the holiday season. Premiering on November 19, the live theatre presentation continues through December 20. Roald Dahl’s beloved story of an extraordinary young girl comes to life in Matilda the Musical. Unloved by her parents, tormented by Headmistress Trunchbull, […]

Downtown Winter Garden Historic District Sign

City to Conduct Re-Survey of Historic Districts

The City of Winter Garden, in collaboration with the Winter Garden Heritage Foundation, has received a grant of $20,000 from the Florida Department of State’s Division of Cultural Resources to conduct a survey of structures located within Downtown Winter Garden’s commercial and residential Historic Districts. A selection of sites located outside the designated districts will […]

Love Local Logo

Winter Garden Announces Love Local Campaign

The City of Winter Garden has launched a Love Local campaign to  build awareness of the importance of supporting the local business community as well as providing programs and activities to help small businesses recover from financial losses due to the COVID-19 pandemic. The Love Local campaign includes a number of initiatives and activities through […]

Halloween Poster 2020

Downtown gets a little Spooky … but not too Spooky

Have you gotten spooked while strolling down Plant Street? The City of Winter Garden will host the Halloween Experience beginning on October 23rd and ending on November 1st.  Walk, drive, ride and stroll down Plant Street and take in all the fun and frightening activities. Local talent, Ian McDaniel, will create and manage the outdoor […]


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