Great Pumpkin Classic
Always double-check with the organizer's website! This page may contain affiliate links.
Great Pumpkin Classic
The Great Pumpkin Classic is a community running and walking event at Trumbull High School in Trumbull, CT, held on October 18, 2026. The event raises funds for the Trumbull High School Scholarship Foundation and the Trumbull Schools PTSA; cumulative scholarship donations exceed $340,000 since 1991 and $8,000 was donated to the THS Scholarship Foundation in the most recent reporting.
- 5K run or walk
- 1.7 mile untimed walk
- Kids fun runs on the track
The 5K is a 3.1 mile, chip-timed race with awards for age groups. The untimed walk follows a mostly flat 1.7 mile route. Kids runs take place on the high school track and include a shirt, finishing medal, and snack. The course used in recent years follows much of the original 1991 routing; it includes an uphill section early on, a downhill segment around 1.0 to 1.3 miles, and a hill late in the course followed by a downhill and flat finish.
Registration is online only and shirt sizing is guaranteed through October 4; no paper or cash registration is accepted on event day. Strollers are permitted and leashed dogs may participate provided they start at the back and are under control. Parking is available at Hillcrest Middle School, the Trumbull High back lot, and the high school football side lot. Police will staff key intersections and some road closures support runner safety. Water stops on course may be limited; participants should plan accordingly. Visit the organization's website for the most recent information.