Downtown Winter Garden News

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


Valentine Couple - Photo Credit: Cricket’s Photo & Cinema

Top 10 Valentine’s Day Downtown Date Ideas

No matter how long you have been together, it’s been said that the most memorable Valentine’s Day gift is time spent together. Fortunately, historic downtown Winter Garden has a number of ways to celebrate the occasion to create a lasting impression. For those wanting some help planning their holiday celebration, here are the Top 10 […]

Children's Statue

Catch Visiting Statue at Downtown Plaza

Downtown Winter Garden is known as a local gathering place for families, with lots of places for children to play and explore such as the splash pad, caboose, trail, as well as a bookstore, music school; and of course, ice cream and candy shops. Therefore, it is only fitting for Downtown to be selected as […]

Drew High School, Class of 1959

Celebrate MLK Day and Black History Month in Winter Garden

The City of Winter Garden is hosting a number of family-friendly activities in celebration of Dr. Martin Luther King, Jr. Day and Black History Month. Please join us in celebrating the life and legacy of Dr. Martin Luther King Jr. as well as commemorating Black History Month with the following:    Pastor Anthony Hodge of […]

Rita's Food

Rita’s brings “Ice Custard Happiness” to Downtown

Downtown is now even sweeter with the opening of Rita’s Italian Ice & Frozen Custard. Offering a variety of irresistible frozen delights made with their famous Italian Ice and Old-Fashioned Frozen Custard, Rita’s friendly staff is excited for its delectable treats to provide a side of happiness. Made fresh daily with real fruit, Rita’s Italian […]

Winter Wonderland at City Hall

Top 10 Holiday Photo Spots

Downtown Winter Garden is idyllically picturesque this time of year exuding Norman Rockwell small town holiday charm. With all the holiday backdrops to choose from, we have compiled the Top 10 Holiday Photo Spots perfect for capturing this year’s memories. #1. Poinsettia Christmas Trees at Centennial Plaza 101 W. Plant Street #2. Holiday Mural Wall […]

Cecilia Lueza Mural 1

Cecilia Lueza Paints Winter Garden’s Second Mural

Downtown Winter Garden’s second mural is being painted as we speak and will be ready to unveil later this month. The location of this new mural will be 49. S. Main Street or the northern wall of Doxology. This initiative is a partnership between the City of Winter Garden and the Winter Garden Art Association.  The […]

HOLIDAY BOUTIQUE STROLL & SALE

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 […]

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