Things to Do | Arts + Entertainment

Arts + Entertainment | Things to Do

Leticia Silva
October 12, 2025

Descent into Madness with Winter Garden Masonic Lodge No. 165

The event will start at 7 p.m. Friday, Oct. 17, and Saturday, Oct. 18 at 230 West Bay Street, Winter Garden.

Arts + Entertainment
Things to Do

Leticia Silva
October 10, 2025

Carlo’s Diner to host first classic car show

The Ocoee diner will host a car show extravaganza from 7 to 10 a.m., Saturday, Oct. 18 at 1500 Wurst Road, Ocoee.

West Orange Times & Observer
News

Liz Ramos
October 10, 2025

Halloween Light Show returns to Winter Garden

Although Halloween Fest will not be happening this year, a spirited lights show will be projected on City Hall.

West Orange Times & Observer
News

Liz Ramos
October 8, 2025

Oakland Nature Preserve carves out Halloween tradition

Oakland Nature Preserve’s popular Pumpkin Glow is set for later this month. There still is time to carve your own entry for this year’s event.

Arts + Entertainment
Things to Do

Michael Eng
October 7, 2025

Warriors on Water plans Wellness Day

The second Paddling Through Healing Waters will be from 10 a.m. to 2 p.m. Saturday, Oct. 11, at the Dr. P. Phillips YMCA Family Center.

Arts + Entertainment
Things to Do

Leticia Silva
October 7, 2025

Windermere Craft Beer Fest back after six-year hiatus

The event will take place from 4 to 8 p.m., Saturday, Oct. 25, at 520 Main St., Windermere.

Arts + Entertainment
Things to Do

Michael Eng
October 7, 2025

Central Florida Railroad Museum clicks into season with Frightfully Fun Lego Night

This event takes place from 5-8 p.m. Friday, Oct. 24, at the museum, 101 S. Boyd St., Winter Garden.

Arts + Entertainment
Things to Do

Michael Eng
October 7, 2025

Windermere rolls with 2025 Halloween Costume Parade and Hayride

This event takes place at 9:45 a.m. Saturday, Oct. 25, at Windermere Town Hall, 520 Main St.

Arts + Entertainment
Things to Do

Michael Eng
October 7, 2025

Yellow Dog Eats plans Halloween costume paw-ty

Barktober Fest will take place from 5:30 to 8:30 p.m. Thursday, Oct. 23, at Yellow Dog Eats, 1236 Hempel Ave, Gotha.

Arts + Entertainment
Things to Do

Michael Eng
October 7, 2025

Horizon West Rotary to tee off with fall golf tournament

The tournament takes place at 8 a. Friday, Oct. 24, at Stoneybrook West Golf Club, 15501 Towne Commons Blvd., Winter Garden.

Arts + Entertainment
Things to Do

Michael Eng
October 7, 2025

Ocoee plans frightfully good time

The city of Ocoee’s Halloween Howl Night will take place from 6-9 p.m. Friday, Oct. 24, at Bill Breeze Park, Ocoee.

Arts + Entertainment
Things to Do

Michael Eng
October 2, 2025

OCOM welcomes fall season with festival

The Horizon West medical school invites the community to its second annual Fall Festival.

Arts + Entertainment
Things to Do

Michael Eng
October 2, 2025

West Orange High School band to host Westside Showcase

The marching band show will take place Saturday, Oct. 18, at Raymond Screws Stadium, 1625 Beulah Road, Winter Garden.

Arts + Entertainment
Things to Do

Michael Eng
October 2, 2025

Prost! Oktoberfest returns to Crooked Can Brewing Company

The Winter Garden brewery will host this event Oct. 17 to 19 at 426 W. Plant St.

Arts + Entertainment
Things to Do

Michael Eng
October 2, 2025

Help build 100 beds at Windermere’s 2025 Community Bunk Bed Build

The community service event takes place from 8 a.m. to noon Saturday, Oct. 18, at 520 Main St., Windermere.

Arts + Entertainment
Things to Do

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