The Chester Chipmunk's Trail Run Challenge is an annual event held during the Trenton Fun Fest offering 1K, 5K, and 10K trail runs suitable for all ages and abilities. Participants enjoy well-maintained gravel trails with gentle rolling hills through scenic Trenton Park.

This inclusive event emphasizes community participation, welcoming runners, walkers, families, and nature enthusiasts to connect with nature and one another in a family-friendly atmosphere.

- Annual event part of the Trenton Fun Fest
- 1K Family Fun Run known as Chester’s Loop finishing at the splash park
- Suitable for all ages and abilities
- Encourages community participation with runners, walkers, families, and nature lovers
- Scenic, well-maintained gravel trails through Trenton Park