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The City of Winter Garden is Celebrating its Founding 118 Years Ago

Winter Garden Fall Heritage & Music Festival on Saturday, November 6, 8:00 am to 10:00 pm.


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  • | 12:00 p.m. November 3, 2021
  • West Orange Times & Observer
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The City of Winter Garden is celebrating its founding 118 years ago with a community-wide Winter Garden Fall Heritage & Music Festival on Saturday, November 6, 8:00 am to 10:00 pm.

The free community event will incude a variety of entertainment for all ages.

  • Live music with 19 bands of various genres across five stage locations throughout downtown plus at the Centennial Plaza Gazebo, as well as at Sam Williams Little League Complex (11:00 am - 10:00 pm). Headliners will include Selwyn Birchwood, Michael Andrew & Swingerhead, Thomas Wynn and Hannah Barber, Hello Sister, and many more top talents.
  • Strolling street performers from jugglers, musicians, to acrobats (2:00 - 9:00 pm)
  • Field games of baseball, softball, football, pickle ball, volleyball, and soccer for children and families at Sam Williams Little League Complex and Veterans Memorial Park (8:00 am - 4:00 pm)
  • A hay maze at City Hall plus fall festivities and decorations
  • Heritage exhibits at the Winter Garden Heritage Museum and Education Center (10:00 am - 3:00 pm)
  • G-scale model railroad, special presentations and tours, 51st anniversary slide show, and more at the Central Florida Railroad Museum (9:00 am - 5:00 pm)
  • Two-mile walking Heritage Trees Tour through downtown (8:30 am at Winter Garden Heritage Museum)
  • Video tour of Winter Garden to learn its history at the Garden Theatre (continuous loop from 12:00 pm - 2:00 pm)
  • Health & Harvest Festival hosted by Healthy West Orange at the Winter Garden Farmers Market (8:00 am - 1:00 pm)
  • Winter Garden Masonic Lodge Fall Festival and the Arts (11:00 am - 4:00 pm)
  • Fall-themed Farmers Market with a Kidz Zone, games on the lawn, and more (8:00 am - 1:00 pm)
  • 5K Donut Dash run/walk presented by the Winter Garden Police Athletic League (8:00 am/pre-registration and fee required)

This event is brought to you by the City of Winter Garden and the Winter Garden Heritage Foundation. For a music and activities schedule and additional information, visit www.downtownwg.com.