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.

By Michael Eng
| 8:53 a.m. October 30, 2025

Arts + Entertainment
Things to Do

Enter — if you dare — as the Winter Garden Heritage Museum turns its beloved Chessie Caboose into a fright zone.

The Spooky Caboose will be open from 3-8 p.m. Friday, Oct. 31, at 21 E. Plant St., Winter Garden.

Climb the steps into the dark recesses of the caboose to see what family friendly frights await.

There will be treats to go along with the tricks!

Free to enter; donations appreciated.

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.