Arts + Entertainment

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

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

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

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

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

Megan Bruinsma
October 27, 2025

Philly Pretzel Factory coming to Winter Garden

The pretzel shop from Philadelphia will be in the Avamar Crossing shopping plaza.

West Orange Times & Observer
News

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

Michael Eng
October 23, 2025

PHOTOS: Windermere High competes at 2025 Bands of America Orlando Regional Championship

The Fightin’ Wolverine Band and Guard competed against some of the best bands in the country.

Observer School Zone

Liz Ramos
October 23, 2025

Windermere Wine & Dine under new leadership

West Orange Foundation takes over Windermere Wine & Dine to elevate the event while maintaining its quality and mission.

Arts + Entertainment

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

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

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

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

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

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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