Fall Events Header​​

Winter Garden has a calendar full of Fall fun headed our way. Join us!

  1. 10/19-10/21 4th Annual Crooked Can Oktoberfest

    426 W. Plant St. Winter Garden, FL
    The 4th Annual Crooked Can Oktoberfest
  2. 10/26, 10/27, 10/28, & 10/31 Panic on Plant Street Haunted House

    104 S Lakeview Ave, Winter Garden, FL
    Downtown Winter Garden's only Haunted House is filled with spine tingling adventure around ever corner! Visit the Facebook page for details.
  3. 10/27 Health & Harvest Festival at the Farmer's Market

    104 S Lakeview Ave, Winter Garden, FL
    Healthy West Orange Harvest Festival will be an exciting day in downtown Winter Garden in conjunction with the Farmer's Market! Commencing with a family bike ride and ending with an evening of feasting on a spectacular farm to table dinner, this special day will include many healthy activities for all ages! Get involved in exercise demonstrations, sample some healthy cooking classes and so much more! Visit the Facebook page for event details and to register. This is an all-day event. Join us between 9am and 10pm.
  4. 10/31 Halloweenfest

    Downtown Winter Garden
    Free Trick or Treating along Plant Street from 6-8pm in Downtown Winter Garden! Trick or Treat along Plant Street with the Downtown Merchants. Features live entertainment, local vendors and family activities! Enjoy a safe night of haunted happenings along downtown Plant Street! If you are interested in becoming a vendor please click here.
  5. 11/1 Winter Garden Wine Walk

    104 S Lakeview Ave, Winter Garden, FL
    If you love great wine, great music, and tasty food, the Wine Walk (6:30 - 9pm) is a great way to enjoy all three. Live music, shopping, fun with friends and you have the makings of an exquisite evening in beautiful downtown Winter Garden.
  6. 11/17 2nd Annual American Legion Challenge 22

    426 W Plant St , Winter Garden, FL
    Come out to join (between 11am and 5pm) the Winter Garden American Legion Post 63, in partnership with the Crooked Can Brewery, & our community for a walk, block party and a day of camaraderie to raise awareness for PTSD & Suicide in Veterans. For more information, visit our event page.