Living local campaign

Living Local Logo

The City of Winter Garden launched a “Living Local” campaign in September 2021 to build awareness of the area’s attributes and special events as well as the importance of supporting small businesses. The Living Local campaign follows the “Love Local” campaign that ran from September 2020-August 2021 to support local businesses and community organizations to assist with recovery from the COVID-19 pandemic.

The intent of the “Living Local” campaign is to encourage exploring the community’s cultural and recreational facilities; patronizing locally owned and operated businesses; buying locally produced goods; taking part in classes, programs, and/or sports leagues offered by the City Parks & Recreation Department; supporting local charitable organizations, attending city government meetings and volunteering to serve on its committees and boards; and, of course, partaking in special events that provide a sense a community and create memorable moments.

A number of events and initiatives are planned for the remainder of 2021 to provide “Living Local” opportunities, including the following:


September 15 – October 15 (dates and times vary)



Celebrate Hispanic Heritage Month in Winter Garden with a variety of cultural and entertainment options to honor the cultures and contributions of Hispanic and Latino Americans. The weekly Farmers Market is hosting an authentic flamenco performance and complimentary Día de los Muertos art class and has a designated section featuring Hispanic and Latino cuisine and merchandise. There will be mariachi and flamenco performances at select Fridays on the Plaza nights in the center of downtown, Mexican art classes at SOBO Art Gallery, showings of Man of La Mancha at the Garden Theatre, as well as virtual events hosted by the Winter Garden Library, and more. The national holiday can also be observed by visiting the many Hispanic- and Latino-owned restaurants throughout the city. Click here for a list of events and ways to celebrated Hispanic Heritage Month in Winter Garden..




The City of Winter Garden proclaims October as Outdoor Dining Month! The refreshing weather is ideal for dining al fresco at the multitude of restaurant patios available in all corridors of the city. In addition, the expansive dining patios in Downtown Winter Garden not only provide a close-up view of the historic charm, but also of the festive Halloween Experience (October 22-31). Fall is also the perfect time for an outdoor picnic so make it easy by ordering take-out from your favorite local restaurant as you head to one of the city’s nature parks.


Launches October 9

Every Saturday, 8:00 am – 1:00 pm

Downtown Pavilion, 104 S. Lakeview Avenue


For 13 years, the nationally award-wining Winter Garden Farmers Market has served as a communal meeting place to enjoy the harvests of local farmers and the crafts of local artisans. On Saturday, October 9, the Farmers Market will expand to more than 100 vendors offering a diverse variety of foods and merchandise in addition to weekly family games on the lawn, a designated kids’ zone with child-oriented food and goods, as well as an arts market showcasing local artists. The date also marks the return of weekly live music. A visit to the community Farmers Market exemplifies Living Local.


October 22– October 31

All Day and Special Programming on Fridays/Saturdays/Sundays Evenings

Downtown Winter Garden

Why celebrate Halloween on one day when the fun can last 10 days! The City’s Halloween Experience, October 22-31, provides family-friendly festivities throughout downtown. Activities include outdoor animated Halloween Light Shows on City Hall as well as live music, shows, and pop-up street performers on Friday/Saturday/Sunday evenings; an outdoor moonlight movie showing of Monster University; a hay maze; holiday-themed photo locations; decorations and light displays; merchant themed decorations and food items; a Harvest Sidewalk Sale & Stroll (Oct. 23), a spooky caboose, Halloween movies at the Garden Theatre, fall themed Farmers Market, and more!


Saturday, October 23

All Day, Downtown Winter Garden


Shop the outdoor racks of sale and fall merchandise while enjoying the Halloween Experience decorations and festivities. It is a great time to purchase for the new season while getting a head start on holiday shopping. The unique shops of downtown feature apparel, jewelry, home décor and greenery, cycling/running/sporting equipment and accessories, gourmet foods, health and beauty products, pet supplies, furniture, and much more. In addition, a number of downtown restaurants will feature seasonal menus and promotions to enjoy while dining at the outdoor patios surrounded by Halloween nirvana. 


Saturday, November 6

11:00 am – 10:00 pm

Downtown Winter Garden & Surrounding Parks


In celebration of Winter Garden’s founding this month 118 years ago, the City of Winter Garden and the Winter Garden Heritage Foundation will host a daylong celebration of the community’s historic roots with old-fashioned family fun. Exhibits and activities will provide an opportunity to learn about the City’s history, play family-friendly games, listen to live music (three stages), enjoy special treats, and watch some baseball. Learn how agriculture along with the railroad, Lake Apopka, and baseball were a big part of Winter Garden’s history. Take a trip back in time and learn about a community that came together to be known as Winter Garden.


Saturday, November 6

8:00 am – 1:00 pm

Downtown Winter Garden

Enjoy family fun games, fitness and cooking classes, and much more at the annual Health & Harvest Festival as an expansion of the Winter Garden Farmers Market. Hosted by Healthy West Orange, activities are complimentary and include health screenings, CPR classes, bike safety checks; nutrition, health and fitness classes, giant-sized yard games, hay maze, live DJ, and other seasonal-related fun. For more information, click here




The City declares the month of November as Living Local Month to promote the importance of shopping, dining, and supporting independently owned local businesses as they continue to recover from financial losses due to the pandemic. In fact, shopping local bolsters the local economy since for every $100 spent at locally owned businesses, $68 will stay in the community, whereas, only $43 remains in the community when shopping at a national chain, according to the Independent We Stand organization. In addition, a robust holiday event season launches this month providing the opportunity to enjoy one's hometown and make memories.


Citywide & Sidewalk Sale in Downtown Winter Garden

Saturday, November 27

All Day


Seasonal shopping kick-off in celebration of nationally celebrated Small Business Saturday. Besides special sales at retail stores throughout Winter Garden, Downtown Winter Garden will host a Sidewalk Sale with special offers and promotions amidst the backdrop of historic charm and festive winter wonderland decorations.


December 1-31 

Downtown Winter Garden


Downtown Winter Garden transforms into a winter wonderland with all the holiday trimmings for family fun all month long! Highlights include nine nights of the animated  “A Very Merry Winer Garden Light Show” projected onto Winter Garden City Hall, variety shows on select Friday and Saturday evenings, 14 nights of horse-drawn holiday carriage tours, holiday-themed Farmers Market, live holiday music at select Fridays on the Plaza, Dickens carolers, outdoor holiday movie for the community, holiday movie showings at the Garden Theatre, festive decorations and light displays, holiday themed photo locations, and more! It's Tis the Season to make memories! For event schedule and additional holiday information, visit


Thursday, December 9

5:00 pm – 8:00 pm

Downtown Winter Garden


Holiday shopping at its finest with a stroll of the boutiques of Downtown Winter Garden to find unique presents while enjoying light refreshments, raffles, outdoor/indoor specials and promotions. The festively decorated stores and downtown area make it a perfect evening for gift buying.

For up-to-date event schedules, classes, programs, and Living Local opportunities, visit the Official Downtown Winter Garden website, and follow the City’s official Instagram and Facebook platforms.

The City of Winter Garden will continue to monitor the COVID-19 outbreak within the community and reserves the right to cancel any activities that are not in the best interest of the public health, safety, and welfare of its citizens.


The City of Winter Garden implemented a Curbside and Outdoor Dining Program for Downtown Winter Garden in May 2020 that continues to be popular and convenient. Since implementing the Downtown Outdoor Dining Program, the City of Winter Garden has worked with restaurants outside of Downtown to establish outdoor dining areas.

Each year, the months of May and October are declared Outdoor Dining Month and are promoted as a safe way for our community to support local restaurants.


The City of Winter Garden implemented the Downtown Ambassador Program in April of 2020 to assist with the Curbside and Outdoor Dining Program for Downtown Winter Garden. The role of Downtown Ambassador is to serve as the face of the City with property and business owners, residents and visitors within the Downtown District.  This program has been very well received. The ambassadors have provided much needed business support and helped with a variety of downtown duties that keeps downtown working and looking its best.


Open for Business Sign in Storefront

Whatever the issue, we are here to assist you. If we can help, please call 407.947.1720.

Please visit Downtown Winter Garden to learn more about what is happening Downtown.  Your official source for everything Downtown.