Things to Do | Arts + Entertainment

Arts + Entertainment | Things to Do

Michael Eng
November 6, 2025

Horizon West’s Flavor Fest set for Saturday

This annual event takes place from 5-9 p.m. Saturday, Nov. 8, in the Hamlin Green Space, 14111 Shoreside Way, Winter Garden.

Arts + Entertainment
Things to Do

Michael Eng
November 6, 2025

Winter Garden Rotary goes all in on poker tournament

The club’s 17th annual Texas Hold ‘Em Poker Tournament takes place at 7 p.m. Friday, Nov. 7, at Tanner Hall, 29 W. Garden Ave., Winter Garden.

Arts + Entertainment
Things to Do

Leticia Silva
November 4, 2025

Winter Garden Hypnosis to host Power of Connection weekend

The event will take place from 9 a.m. to 5 p.m. Friday, Nov. 7 to Sunday, Nov. 9 at Flamingo Crossings, 13295 Hartzog Road, Winter Garden.

Southwest Orange
News

Megan Bruinsma
November 4, 2025

Ocoee Fire Department hosting an open house

The City of Ocoee’s Fire Department is hosting its annual open house Saturday, Nov. 8.

Arts + Entertainment
Things to Do

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

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

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

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 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

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

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