Costumes encouraged!

5K Run/Walk

$40 $15 8:00AM EDT - 9:10AM EDT
365 spots left. Price increases after June 1, 2024 at 11:59pm EDT
Free race for the little ones

Kid's Dash

$0 7:45AM EDT - 7:50AM EDT
75 spots left. Registration ends October 26, 2024 at 7:45am EDT
Open to ages 2 - 12.


Be a part of our charity race through the historic district of Longwood. All of the proceeds will go to benefit historic preservation in Longwood via the Longwood Historic Society. The society maintains three buildings within the district built in the 1870s and 1880s. We need your help to raise money for the continued restoration and preservation necessary to keep them around for another generation! The race will begin and end at the Historic Civic Center in downtown Longwood's historic district.

It will be fun, family-friendly, and Halloween-themed. 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.

The Longwood Historic Society is a non-profit and contributions are tax-deductible. 100% of the proceeds from the race will go to the Society and its primary mission to preserve and restore our historic buildings. Our goal for this year is to raise enough money to replace the roof on the Inside-Outside House (Cottage Gift Shop). Thanks for your help!!!

Athlete Guide

We have prepared a race program for participants.

Download it


The awards ceremony will be held at 9:15 AM after the walkers finish. We will start with the costume awards, then overall, and finally, age group awards. Results are posted live, so you can find out where you finished. If you need to leave early, we can give you your medal based on live results at 9 AM. We will not ship awards.

Finish place is based on NET TIME (when you cross the start and finish), not necessarily the order of finish. We will start the races in waves, so runners in other waves may beat your time.


The top three men and top three women overall will receive a plaque and gift certificate.

Age Group Awards

The top three in each age group get a medal.

12 & Under, 13-14, 15-19, 20-24, 25-29, 30-34, 35-39, 40-44, 45-49, 50-54, 55-59, 60-64, 65-69, 70+

Kids Dash Ribbons

Each participant will get a "Fun Run" ribbon.




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.

135 West Church Avenue
Longwood, FL 32750


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).

Course Map

We will use the same course that we have used since 2020. It is a single-loop course that starts in the historic district, winds through neighborhoods, loops around Reiter Park, and then back where it started.






In Kind

Race Contact Info

If you have any questions about this race, click the button below.

About the Longwood Historic Society

The Longwood Historic Society is a non-profit organization charged with preserving the three 1880s buildings that 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 and connecting us with our area's rich legacy and conserving stories and records of prior generations.

Learn more about the society or become a member.

Become a Sponsor

2023 Sponsor Packet

Our sponsors are the lifeblood of this event. The Monster Dash is the Longwood Historic Society's most important fundraiser. Please consider promoting your business for a good cause!



Historic Civic Center
135 W Church Ave
Longwood, FL 32750


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In Kind

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