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Chilling Nights in Winter Park

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Tour Overview

An actress who never left the stage after her final curtain call? German prisoners of war still toiling in the orange groves years after the war is over? The spirit of an artist who couldn’t leave his work unfinished?

Come along for a spooky tour through the old bricked streets of Winter Park. For years people would migrate from the north to Winter Park to escape the cold, but some never left as the weather warmed up. This city, with over 100 years of history, has plenty of unusual tales that will make your skin crawl.

While visiting decrepit haunts and grisly sites, you’ll learn the unspoken history of this unsuspecting town, guaranteed to leave your spine-tingling.

Join us for a night of informative, yet entertaining, storytelling filled with creepy tales. We promise to ward off the spirits during the tour, but you’ll leave the night wondering if there’s something paranormal hiding in the dark.


Tour Includes:

  • Guided walking tour through Winter Park
  • Haunting stories from locals of unusual occurrences
  • Historical information about the surrounding area
  • Interesting facts about the buildings and historical figures in town
  • 10% discount for your next Original Orlando Tours adventure (valid for 30 days)
  • Orlando discount booklet for each guest
  • Confirmation will be sent within 48 hours of booking, subject to availability
  • A minimum of 2 people per booking is required
  • The minimum age of all our guests is 6 years old

Exclusions and Extras:

  • Tour guide gratuity is not included in the booking price.


Approximately 2 hours in total. This tour typically operates on Thursday evenings most months of the year.

Cancellation Policy:

You may receive a full or partial refund by notifying us via email at info@originalorlando.com of the cancellation. No refunds shall be issued for cancellations not received at least 72 hours in advance of the starting time and date of your tour. Please review your Terms and Conditions document for other cancellation provisions.

Sunny’s Local Tips and Bits:

The world-famous “Temple” orange was discovered in Winter Park and developed in the surrounding groves. The original tree still stands on private property within the city. Mr. Rogers met fellow music student and his future wife, Sara Joanne Byrd, on the campus of Rollins College in Winter Park.


This historical ghost walking tour is only offered in English. Florida weather is unpredictable and may impact the tour. If the weather is deemed unsafe by our guide due to weather conditions prior to commencement of the tour, Original Orlando Tours will offer a substitute tour at the original day and time, offer a credit to be used on any future Original Orlando Tours adventure, or fully refund the tour fee, the choice of which is at the option of our special guests impacted by the weather disruption. There are no refunds once the tour has commenced (i.e., the group has left your departure point). This train tour also includes an Orlando discount savings booklet. We suggest wearing a hat, comfortable shoes and sunscreen to make your tour an enjoyable one in warm months as well as a jacket in cooler weather.

Not Available
Tour type: Specific Date
Maximum number of people: 16


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