Where do the race proceeds go?

All proceeds benefit the Longwood Historic Society, a non-profit organization dedicated to the restoration and preservation of historic buildings in the district.

Is there a kids' race?

Yes, there is a free kids' dash held immediately before the 5K event.

Are costumes allowed?

Yes, the event is Halloween-themed and runners are encouraged to wear costumes, with prizes awarded for the best ones.

All races

3 weeks out

Not affiliated with this event. Official website. We may earn a commission on registrations.

All races

3 weeks out

Longwood Monster Dash

Saturday, October 31, 2026Longwood, FL200m – 5K

Join the community for a spirited charity run through the heart of Longwood's historic district. This Halloween-themed event invites runners of all ages to don their best costumes for a chance to win prizes while supporting a great cause. The race begins and ends at the Historic Civic Center, winding through an area rich with architecture dating back to the 1870s and 1880s. Every registration fee directly benefits the Longwood Historic Society, with this year's proceeds dedicated to restoring the roof of the iconic Bradlee-McIntyre House. Enjoy a festive atmosphere filled with Halloween music and family-friendly fun, including a free kids' dash held just before the main 5K. It is a perfect opportunity to combine your love for running with the preservation of local history.