Longwood Monster Dash

Lace up your running shoes and embrace the spooky spirit at the Longwood Monster Dash on October 24, 2026, in Longwood, FL! This annual, family-friendly event invites runners of all ages to enjoy a Halloween-themed experience while supporting a vital cause. Participants can choose between a chip-timed 5K Run/Walk or a free, untimed 200M Kids' Dash, making it perfect for both competitive spirits and little monsters.

The course itself offers a charming journey through Longwood's historic district, starting and finishing at the Historic Civic Center. Runners will wind through picturesque neighborhoods and Reiter Park, passing architectural treasures from the 1870s and 1880s, providing a unique and scenic backdrop to your run. Expect a generally flat course, characteristic of the area, making for an enjoyable run. Hydration is available with a water station near the halfway point on Bearss Circle, along with water and a pre-race fueling station at the start/finish area. Typical race day conditions in late October include comfortable highs around 83°F and lows near 64°F, with a low 8% chance of precipitation, creating pleasant running weather.

What truly sets the Longwood Monster Dash apart is its lively atmosphere and charitable heart. Costumes are highly encouraged, with prizes awarded for the best outfits, and Halloween-themed music fills the air, adding to the festive mood. Every 5K finisher earns a unique wood medal, while the top three overall male and female finishers receive a trophy. Critically, all proceeds from the race directly benefit the Longwood Historic Society, aiding their mission to preserve and restore the area's historic landmarks, such as the Bradlee-McIntyre House. Join this event for a fun run, a scenic tour, and the chance to contribute to local history.