Ghosts of 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? What is the huge connection that Alfred Hitchcock’s “Psycho” has to Winter Park? Solve all these mysteries on your Winter Park ghost tour!

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 on this Winter Park ghost tour. We promise to ward off the spirits during your visit, but you’ll leave the night wondering if there’s something paranormal hiding in the dark.

Tour Includes:

  • 90 minute Guided Ghost Walking Tour through Winter Park.
  • Haunting tales from the fascinating history of Winter Park.
  • Interesting facts about the buildings and pioneers who founded and grew the town.
  • Every person age 4 and up on the tour must have a ticket.
  • 10% discount for your next Original Orlando Tours adventure (valid for 30 days).
  • Please reserve in advance.
  • Confirmations will be sent within 48 hours of booking, subject to availability.
  • Not recommended for children under 4.

Exclusions and Extras:

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


The tour lasts approximately 90 minutes.

Tours originate from the benches in front of the City of Winter Park Administrative Building, located at 401 South Park Avenue (southwest corner of South Park Avenue and West Lyman Avenue), Winter Park 32789. There is free parking behind the building and along the local streets in the area. If coming from the I-Drive or Orlando tourist zones, you may want to allow at least 45 minutes travel time depending on your departure location; check your GPS, Waze, Google Maps or other apps so you can be sure to join our tour in plenty of time.

This tour typically operates on select Thursday evenings during most months of the year. Check the schedule on this page for exact dates.

Please arrive between 7:15pm and 7:20pm; tours depart promptly at 7:30pm.  There are no refunds or partial credits for guests who are late to the tour or no-shows. Tours depart rain or shine!

Private and Large Groups:

A private tour (ten or more) can be designed for your group to deliver a customized, extraordinary evening!  For groups of ten or more, please contact Sarah at or (407) 986-8687 to create your unforgettable visit!

Cancellation Policy:

You may receive a full or partial refund by notifying us via email at of the cancellation. No refunds shall be issued for cancellations not received at least 24 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 Annie Russell Theatre on the campus of Winter Park’s Rollins College was built in the 1930s and named after the actress, Annie Russell, who taught at the school. She came out of retirement to perform again on-stage opening night in 1932, and them passed away just four years later.

Students and maintenance staff have often reported seeing a female ghost in the second-story changing room…and other parts of the campus!


This historical ghost walking tour is only offered in English. Florida weather varies throughout the year, so you may want to check the forecast and plan to dress accordingly. Tours operate rain or shine! We suggest wearing comfortable shoes and bringing an umbrella if there is a chance of rain.

Adult Admission: Ages 13+

Child Admission: Ages 4-12

Not Available
Tour type: Daily Tour
Duration: 1.5-2 Hours
Maximum number of people: Unlimited


100% of guests recommend

5 of 5 guest rating

based on 6 reviews

  • "What Fun!!!"
    Thoroughly enjoyed this night out!!! Sarah, we will be back I promise you! Thank you!!!
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  • "Ghosts, jokes and pub stop"
    I have to echo the review above. This was just a fun night out. Definitely recommend it.
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    Was this review helpful? 3 like this

  • Chantelle

    1 Review
    "Local and Loved It!"
    OK, to be honest, when my friends roped me into this, I thought a tour of Winter Park, even a ghost tour, would be lame. Back it up, girl! You won me over, Michael! You are a fabo guide, loved the stories and as I said last night I want to bring out a bunch of my sorority sisters next semester.
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  • "Yes, kid friendly fun!"
    Was a little skeptical if this would be OK for children (8-boy, 9-girl), but they had so much fun too. There is a stop at a small pub that was very nice and kid-friendly. There is a lot of walking (even though there are many stops), so I wouldn't recommend kids much younger than mine going unless you have a stroller or don't mind carrying them.
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  • "Family Fun Chills"
    Our family loved it. Great tour for adults and children alike. The guides checked with us ahead of time to gauge what kind of stories to tell with our kids. Extra effort goes a long way! 10/10
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  • "Really enjoyed it!!!"
    What great fun! Perfect blend of scary and entertaining. We really had a great time and it was a perfect way to safely get back out and do something really fun as a group.
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