The best things to do in Winter Garden, Windermere, Horizon West, Dr. Phillips for Oct. 19-22

By Michael Eng
| 7:45 a.m. October 19, 2023

Arts + Entertainment
Things to Do

Ocoee High School’s “The Plot, Like Gravy, Thickens”
Ocoee High School will present “The Plot, Like Gravy, Thickens” at 7 p.m. Thursday, Oct. 19, Friday, Oct. 20, and Saturday, Oct. 21, at Ocoee High School, 1925 Ocoee Crown Point Parkway, Ocoee. General admission $12; reserved seating $15.

Visit teachtix.com/ocoeehs/the-plot-like-gravy-thickens

Windermere High School’s Fall Musical “Mary Poppins”
Windermere High will present “Mary Poppins” at 7 p.m. Thursday, Oct. 19, Friday, Oct. 20, and Saturday, Oct. 21; and at 2 p.m. Sunday, Oct. 22, at Windermere High School, 5523 Winter Garden Vineland Road, Windermere.

Visit teachtix.com/whs/mary-poppins.

Crookede Can's Oktoberfest takes place Oct. 20-22.

Crooked Can Oktoberfest
Crooked Can will host its annual Oktoberfest event Friday, Oct. 20, through Sunday, Oct. 22. Free.

For more, call (407) 395-9520.

Lift Disability Network’s Cornhole Tournament
This tournament takes place at 10 a.m. Saturday, Oct. 21, at Live Oaks Community Church, The Villages.

Sponsorships start at $500.

For more information, visit liftdisability.net.

The Hamlin Cruise-In returns Saturday, Oct. 21.

Hamlin Cruise-In
This classic car show takes place from 4 to 7 p.m., Saturday, Oct. 21, outside Cinépolis in Hamlin, 14111 Shoreside Way, Winter Garden.

For more, visit hamlincruisein.com.

West Orange Habitat's Rock the House returns Oct. 21.

West Orange Habitat for Humanity’s Rock the House
This annual fundraiser for the West Orange Habitat for Humanity takes place at 6 p.m. Saturday, Oct. 21, at the McKinnon Grove Family Farm, Winter Garden

Tables start at $500.

For more, visit westorangehabitat.org/rock-the-house.

The Bears Who Care 5K takes over Horizon West Sunday, Oct. 22.

Bears Who Care 5K
This 5K will take place from 7:30 to 10 a.m., Sunday, Oct. 22, at 17000 Porter Road, Winter Garden.

author

Michael Eng

As a child, Editor and Publisher Michael Eng collected front pages of the Kansas City Star during Operation Desert Storm, so it was a foregone conclusion that he would pursue a career in journalism. He holds a journalism degree from the University of Missouri — Columbia School of Journalism. When he’s not working, you can find him spending time with his wife and three children, or playing drums around town. He’s also a sucker for dad jokes.