Fall is in the air — even in Central Florida we bring the magic, pumpkin spice (and sometimes rain). Whether your crew loves spooks, tricks, treats, or just some good fall fun, here’s your ultimate local guide to fall 2025. Don’t let your family miss out — keep scrolling for the biggest list of Winter Garden-Ocoee fall and Halloween events happening in 2025!
Last updated: October 27, 2025
🍁 Family-Friendly Winter Garden-Ocoee Fall & Halloween Attractions Nearby and Open All Season Long
These local farms, corn mazes, and haunted attractions are open multiple weeks during the season, offering the perfect blend of fall fun and Halloween thrills:
The Williams Holiday House
- Dates: September 27 – November 1 (Everyday)
- Location: 15304 Oakland Ave., Winter Garden, FL 34787
- Please note this is a private residence, do not enter outside of the posted times.
Southern Hill Farms Fall Festival
- Dates: September 27 – November 23 (Thursdays–Sundays)
- Location: 16651 Schofield Rd, Clermont, FL 34714
- Fun Zone, wagon rides, yard games, live music, 5-acre corn maze and more
- Purchase tickets in advance
Club Lake's Annual Fall Festival
- Dates: September 27 – October 31 (Thursdays–Sundays)
- Location: 3403 Rock Springs Rd, Apopka, FL 32712
- Pumpkin patch, maze, hayrides, kids zone and more
- More Details Here
Great Scott Farms
- Dates: September 27 – November 16 (Saturday and Sundays)
- Location: 26216 County Road 448A, Mount Dora, FL 32757
- Pumpkin patch, corn maze, hayrides and more
- More Details Here
Some of these events are weather-dependent. Always confirm details before heading out.
🎃 Winter Garden-Ocoee Halloween & Fall Fun Events
Please note: Many Winter Garden-Ocoee fall and Halloween events haven’t been announced yet. We’ll keep updating this guide as new details come in. Be sure to bookmark this page and check back often for the latest!
💡 Know about a family-friendly fall festival, Halloween event, or trunk-or-treat in Winter Garden-Ocoee that’s not listed? Submit your event here.
🍂 Week of Oct 3–10
Friday, Oct 3
- Kawaii Monster Party - Lucky Straws Boba Tea
Tuesday, Oct 7
- Things that Go Bump in the Night: Nocturnal Creatures - Winter Garden Library
- Kids Casper Themed Halloween Party - Uno Pizzeria & Grill
- Halloween Trivia with Puzzles Entertainment - Crooked Can Brewing Company
Friday, Oct 10
- Trick or Treat Market Crawl - Home State Brewing Co.
🎃 Week of Oct 11–17
Saturday, Oct 11
- Cork Pumpkin Craft - Bike Life Cafe
Tuesday, Oct 14
- Little Chef: Monster Smash Trail Mix - Winter Garden Library
- Wild Things Rumpus - West Oaks Library
Wednesday, Oct 15
- Preschool Party - Boogie in the Boneyard - Winter Garden Library
Thursday, Oct 16
- Cats, Bats & Babies - Winter Garden Library
Friday, Oct 17
- Halloween Spooktacular Preschool Holiday Program - Jessie Brock Community Center
- Trunk or Treat - Emmaus Church Winter Garden
- Halloween Movie Night & Costume Party - Innovation Montessori High School
- Halloween Golf Cart Parade - Summerport
🍁 Week of Oct 18–24
Saturday, Oct 18
- 2nd Annual Fall Festival - Lakeview Middle School
- Family Fall Festival - Inspired Living at Ocoee
- Halloween Boo Bash - The Grove
- Pumpkin Patch Dash Kids Run - Park at Tildenville Elementary School
- Fall Festival - Orlando College of Osteopathic Medicine (OCOM)
Monday, Oct 20
- The Great Pumpkin Workout - online
Wednesday, Oct 22
- Fall Family Fun Night - St. Luke's United Methodist Church at Windermere
- Pumpkin Painting & Hocus Pocus Movie- The Whole Enchilada
Thursday, Oct 23
- Oakland Farmer's Market - Trick or Treat the Trail - Oakland Market
- I'm not scared! - Winter Garden Library
- Jack-o-Lantern Carving - Oakland Nature Preserve
Friday, Oct 24
- Frightfully Fun LEGO Night- Central Florida Railroad Museum
- Trunk or Treat - The Nest School
- Trunk or Treat - Cranium Academy of Winter Garden
- Ocoee — Halloween Howl Night - Bill Breeze Park
- Trunk-or-Treat -The Learning Experience (Windermere)
- Pumpkin Glow Jack-O-Lantern Trail - Oakland Nature Preserve
- Fall Festival - My Kids Academy
- Halloween Light Show - Winter Garden City Hall
👻 Week of Oct 25–31
Saturday, Oct 25
- Halloween Celebration - Winter Garden Farmers Market
- LEGO Day at the Museum (FREE) - Central Florida Railroad Museum
- Halloween Costume Parade & Hayride - Windermere Town Hall
- Children’s Lighthouse 20th Fall Festival - Children's Lighthouse
- Monster Mash - Windermere Brewing Company
- Halloween Flix at the Garden (Hocus Pocus) - Garden Theatre on Plant
- Cuisine Corner Junior Spooky Snacks - Windermere Library
- Hamlin Pumpkin Patch (FREE) - Green Space outside Cinepolis Hamlin
- Fall Fest - Crossline Park
- Trunk-or-Treat - The Learning Experience (Horizon West)
- Fall Festival - Found Life Church
- Pumpkin Glow Jack-O-Lantern Trail - Oakland Nature Preserve
- Halloween Light Show - Winter Garden City Hall
- Halloween Flix at the Garden (A Nightmare on Elm Street) - Garden Theatre on Plant
Sunday, Oct 26
- Kids Halloween Party & Costume Contest - VFW Post 4305
- Halloween Spooktacular Pet Costume Contest - Crooked Can Brewing Company
- WUG Trunk or Treat - Windermere Union Church
- Trunk or Treat - First Baptist Church of Winter Garden
- Trunk or Treat - West Orange Church of Christ
- Halloween Light Show - Winter Garden City Hall
Tuesday, Oct 28
- Little Chef: PB&J Spiders - Winter Garden Library
- Open House Fall Festival Fun- AdventHealth Well +65
- Pumpkin Decorating - Unos Pizzeria & Grill
- Trunk or Treat - Texas Roadhouse Ocoee
- Trunk or Treat Community Event - HCA Florida West Orange Emergency
Wednesday, Oct 29
- Truck or Treat - Windermere High School
Thursday, Oct 30
- Little Monster Mash - Roper YMCA
- Homeschool Branch Out - Halloween Party - Windermere Library
- Maxey PTA Trunk or Treat - Maxey Elementary School
- Haunted House Escape - Winter Garden Library
- Halloween Music Bingo - Rock 'N Rev Ocoee
Friday, Oct 31
- Spooky Caboose - Outside the Winter Garden Heritage Museum
- Fall Fest 2025 - Christ Chapel, FL
- Trunk or Treat - Faith Family Community Church
- Fall Festival - Glad Tidings Church
🍂 Week of Nov 1–7
Saturday, Nov 1
- Annual Fall Festival - Stoneybrook West Golf Club
- Trick-or-Treat - Downtown Winter Garden
- Halloween Flix at the Garden (The Nightmare Before Christmas) - Garden Theatre on Plant
Sunday, Nov 2
- Annual Fall Festival - Stoneybrook West Golf Club
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👉 Check back often, as we’re adding more Halloween events and spooky fun happenings in Winter Garden-Ocoee all season long!
Know of a Halloween event in Winter Garden-Ocoee that should be listed? Submit it here.
