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Downtown Winter Garden’s Halloween home stretch: free City Hall light shows, a $5 Poltergeist and the Spooky Caboose

Winter Garden still has four free Halloween light shows on City Hall (Oct. 23, 24, 30 and 31), a $5 Poltergeist at the Garden Theatre on Oct. 27, a one-night illusion show…

Orange Halloween projections of a full moon, bare trees, and a pumpkin glow on the front of Winter Garden City Hall at dusk as a crowd gathers outside
Photo: City of Winter Garden

Downtown Winter Garden still has two weekends of free Halloween light shows on City Hall, one more $5 horror classic, a one-night illusion show and a full Halloween Saturday on deck.

Quick Facts

  • Halloween Light Shows: Oct. 23, 24, 30 and 31, 7–9 p.m., Winter Garden City Hall, 300 W. Plant St. Free.
  • $5 Halloween Flix: Poltergeist, Tuesday, Oct. 27, 7 p.m., Garden Theatre on Plant, 160 W. Plant St.
  • Haunted Illusions: Thursday, Oct. 22, 7 p.m., Garden Theatre on Plant
  • Halloween at the Farmers Market: Saturday, Oct. 31, 8 a.m.–1 p.m., kids’ crafts 9 a.m.–noon
  • Spooky Caboose: Saturday, Oct. 31, 3–8 p.m., Winter Garden Heritage Museum, 1 N. Main St. Free; donations appreciated.

City Hall gets haunted

On four more Friday and Saturday nights, Oct. 23, 24, 30 and 31, the city projects family-friendly Halloween animations onto the front of City Hall. Expect ghosts, goblins, witches and creepy crawlers, all synced to spooky music. The show runs on a continuous loop from 7 to 9 p.m., so you can walk up anytime, watch a few rounds and wander down Plant Street for dinner. It’s free, and it runs on Halloween night too.

One more horror classic for $5

The historic Garden Theatre on Plant wraps its $5 Halloween Flix series with Poltergeist (PG) on Tuesday, Oct. 27, at 7 p.m. Tickets are $5 plus a 79-cent fee, sold online only, with assigned seats, and all sales are final. Popcorn, candy and drinks are sold inside, and the theater only takes cards.

The setting helps. The 295-seat theater was built in 1935 and modeled after a Spanish courtyard, with balconies, a Spanish tile roof and a dark blue ceiling full of stars.

A night of illusions

The Garden Theatre also hosts Haunted Illusions starring David Caserta, a one-night-only show of illusions and interactive storytelling, on Thursday, Oct. 22, at 7 p.m.

Halloween day downtown

On Saturday, Oct. 31, the Winter Garden Farmers Market gets spooky decorations and free Halloween crafts for kids from 9 a.m. to noon at the Parking Garage Plaza, and you can pick out a pumpkin for carving while you’re there. Later that day, from 3 to 8 p.m., the Chessie Caboose outside the Winter Garden Heritage Museum becomes the Spooky Caboose, with family-friendly frights and some treats. It’s free to enter, and donations are appreciated. Then stay downtown for the last light show of the season on City Hall.

Why We’re Hyped

You can still get a whole Halloween season within a few downtown blocks for almost nothing: free light shows on four more nights, a $5 classic in a 1935 theater, and a Halloween Saturday that runs from the morning farmers market to the caboose to City Hall after dark.

The Details

  • Halloween Light Shows: Fridays and Saturdays, Oct. 23–24 and 30–31, 7–9 p.m., Winter Garden City Hall, 300 W. Plant St., Winter Garden, FL 34787. Free. City info
  • $5 Halloween Flix: Poltergeist, Tuesday, Oct. 27, 7 p.m., Garden Theatre on Plant, 160 W. Plant St. $5 plus fee, online only. Details and tickets
  • Haunted Illusions starring David Caserta: Thursday, Oct. 22, 7 p.m., Garden Theatre on Plant
  • Halloween at the Farmers Market: Saturday, Oct. 31, market 8 a.m.–1 p.m., kids’ crafts 9 a.m.–noon at the Parking Garage Plaza. Free crafts.
  • Spooky Caboose: Saturday, Oct. 31, 3–8 p.m., Winter Garden Heritage Museum, 1 N. Main St. Free; donations appreciated.

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