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Arts + Entertainment | Things to Do

    By
  • Leticia Silva
  • October 31, 2025
Healthy West Orange to host annual Health & Harvest Festival

The event will take place from 8 a.m. to 1 p.m. Saturday, Nov. 8, at Winter Garden’s farmers market.

  • West Orange Times & Observer
  • Neighborhood
    By
  • Michael Eng
  • October 30, 2025
Town of Windermere to host first Lakes Cleanup Day

The cleanup begins at 1:15 p.m. Sunday, Nov. 2, at Fernwood Park, 632 Butler St., Windermere.

  • Arts + Entertainment
  • Things to Do
    By
  • Michael Eng
  • October 30, 2025
West Orange chamber tees off with Fall Golf Classic

The tournament takes place at 9 a.m. Monday, Nov. 3, at West Orange Country Club, 3300 West Orange Country Club Drive, Winter Garden.

  • Arts + Entertainment
  • Things to Do
    By
  • Michael Eng
  • October 30, 2025
Stoneybrook West Golf Club celebrates season with Fall Festival

This event takes place from 3-10 p.m. Saturday, Nov. 1, and noon to 6 p.m. Sunday, Nov. 2, at 15501 Towne Common Blvd., Winter Garden.

  • Arts + Entertainment
  • Things to Do
    By
  • Michael Eng
  • October 30, 2025
Spooky Caboose chugs into downtown Winter Garden

The Winter Garden Heritage Museum will host a special event to celebrate Halloween from 3-8 p.m. Friday, Oct. 31, at 21 E. Plant St., Winter Garden.

  • Arts + Entertainment
  • Things to Do
    By
  • Leticia Silva
  • October 28, 2025
Animal Clinic of Windermere to host annual open house

Open house will take place from 10 a.m. to 2 p.m. Saturday, Nov. 1, at 1909 Maguire Road, Windermere.

  • Southwest Orange
  • News
    By
  • Megan Bruinsma
  • October 28, 2025
Run, ruck or walk for veterans in Horizon West American Legion’s 5K

The Veteran’s Appreciation 5K Fun Run will take place at Home State Brewing Co. in Horizon West.

  • Arts + Entertainment
  • Things to Do
    By
  • Leticia Silva
  • October 28, 2025
Rotary Club of Dr. Phillips to host annual tasting event

The Taste of Dr. Phillips will take place from from 1 to 4 p.m. Sunday, Nov. 2 at 7958 Via Dellagio Way, Orlando.

  • Southwest Orange
  • News
    By
  • Megan Bruinsma
  • October 24, 2025
Lego day in Winter Garden

The Central Florida Railroad Museum will display a Halloween and Holiday-themed Lego model railroad.

  • Arts + Entertainment
  • Things to Do
    By
  • Liz Ramos
  • October 21, 2025
Southern Hill Farms creates a-maze-ing corn maze

The farm is celebrating 10 years of its Fall Festival with a corn maze that pays homage to owner David Hill’s baseball history.

  • Southwest Orange
  • Neighborhood
    By
  • Leticia Silva
  • October 20, 2025
Halloween pet costume contest coming to Crooked Can

Nonprofit Our Cause 4 Paws Rescue is hosting a Halloween pet costume from 11 a.m. to 2 p.m. Sunday, Oct. 26 at Crooked Can Brewing Co., at 426 W. Plant Street, Winter Garden.

  • Arts + Entertainment
  • Things to Do
    By
  • Leticia Silva
  • October 16, 2025
Ocoee to host girls golf day inspired by Harry Potter

The Girls Golf First Tee of Central Florida are hosting an afternoon of fun filled with magic from noon to 2 p.m. Saturday, Oct. 18 at Forest Lake Golf Club.

  • Arts + Entertainment
  • Things to Do
    By
  • Leticia Silva
  • October 16, 2025
Oktoberfest brewing at Crooked Can

Crooked Can Brewing Co. is bringing back the biggest Oktoberfest in Central Florida for three days full of beer, food and entertainment as well as a new VIP area.

  • West Orange Times & Observer
    By
  • Leticia Silva
  • October 15, 2025
Run, don't walk to sign up for the Pumpkin Patch Dash 5K

The West Orange Junior Service League is hosting its 16th annual 5K run starting at 6 p.m. Saturday, Oct. 18 at Oakland Park.

  • West Orange Times & Observer
    By
  • Leticia Silva
  • October 14, 2025
Gymnastics USA to host Halloween bash

The event will take place from 6:30 to 11 p.m. Friday, Oct. 17 at 1375 W. Colonial Drive, Winter Garden.

  • West Orange Times & Observer
  • News
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