5K SOLD OUT! Join the wait list
We hit record numbers this year, and the 5K sold out on October 19, 2026. Sorry to anyone who didn't get in this year, but we have a wait list and will likely open a few more slots. We still have room for more kids in the Kid's Dash, and we'd love for you to come out to enjoy the music, vendor village, cheering on our runners, and the festivities.
Thank you for all the great support, Seminole County!!!
We may open up a few additional spots if there are dropouts or if we can order more shirts and medals in time. Join the wait list.
Sponsors List
All Levels Sponsors
2026 Info
Join us for our 9th annual race through the Longwood Historic District. It will be a fun, family-friendly, and Halloween-themed event. We invite runners to wear costumes and will award prizes for the best costumes. There will be a free kids' dash immediately before the 5K. We will play plenty of family-appropriate music, including Halloween favorites, to get you into the spirit.
All proceeds will benefit the Longwood Historic Society. Contributions are tax-deductible. Our mission is to preserve our historic buildings and promote Historic Longwood. We aim to raise the funds to repair the rotten wood and reopen the wrap-around porch of the Bradlee-McIntyre House, built in 1885. Thanks for your help!!!
What do you get?
- Chip-timed race by Elite Timing with live results
- An excellent course with a passionate staff and a super-fun, family-friendly vibe
- Tech shirt with our cute mascot logo
- Wood medal for every finisher
- Custom bib number with Monster Dash logo
- Pre-race fueling station with snacks and fruit
- Water at the start/finish and halfway point
- Free Coffee from Claro's Coffeehouse
- Prizes for best costumes in multiple categories
- Prizes for the top three male and female overall finishers
- Trophy for largest team
- A physical packet with a branded bib and coupons to local businesses
- Photos posted after the race
- DJ playing holiday-themed music
Schedule
Friday
10AM - 6PM - Early Packet Pickup
Saturday
7:00 AM - Late Packet Pickup
7:15 AM - DJ Starts Spinning Music
7:35 AM - Opening Announcements and Welcome
7:45 AM - Kid's Dash
8:00 AM - 5K Start
8:16 AM - The first runners finish
9:10 AM - The last walkers finish
9:15 AM - Awards Ceremony and Costume Contest
Packet Pickup
Packets will be available for early pick-up on Friday before the race from 10 AM until 6 PM. This is a great way to beat the rush on race morning. If you can't make it then, you can pick up your packet between 7 AM and 8 AM on race morning.
Packets will include your bib number (with chip), safety pins, promotional material from our sponsors, and a shirt.
Location
Our course starts and ends in beautiful Historic Longwood. It tours you through Reiter Park and neighborhoods. The start/finish line is in the same spot, right in front of the Longwood Historic Civic Center and race headquarters.
Parking
There is plenty of free parking in downtown Longwood. There is a city lot, across from the Longwood Community Building on Warren Avenue. The City Hall complex, Longwood Inn, behind the hospital, and Reiter Park all have many spaces. Overflow parking in the Sun Rail parking lot and garage, just across Highway 427 (Ronald Reagan Blvd), is also available (Sun Rail does not run on Saturdays).
Free Coffee
Claro's Coffeehouse of Historic Longwood will offer free drip coffee to participants. Espresso drinks will be available for a charge.
DJ Jorge
Our MC this year is a local favorite DJ Jorge Quinones. He will keep the atmosphere live for us.
Shirts and Bib Numbers
Our tech shirts are made of a wicking, dry-fit material that is among the most comfortable you will ever wear. This year, we're going with black.
The custom-printed purple bib numbers have the RFID timing chip built in.
Awards
Every finisher will receive a custom award, printed on textured leatherette and mounted on a wooden base. They will receive a ribbon to wear around their neck or display in their award case. We enjoy giving distinctive awards that feel unique and use sustainable materials rather than metal.
Trophies like these will be awarded to our top three male and female overall, the largest team award, and to our eight costume constest category awards.
Course
Here is a link to the zoomable course map: https://www.gmap-pedometer.com/?r=7509184
We start and finish in front of the Historic Civic Center.
Dry Fit Shirts
Longwood Historic Society
The Longwood Historic Society is a non-profit organization charged with preserving the three 1880s buildings we own in downtown Longwood: the Bradlee-McIntyre House, Historic Civic Center, and the Inside-Outside House. We also serve as a civic organization to promote the community by putting on events, connecting us with our area's rich legacy, and conserving stories and records of prior generations.
Questions?
Check out our Frequently Asked Questions page.
Contact Us
Lil' Frank
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