Trail Running calendar near Boonville 2025-2026

Join the Black Annie Trail Race at Scales Lake Trails in Boonville on Nov 16, 2025. Choose 5K, 10K or 15K by completing one to three laps of a scenic 3.35 mile loop. Finishers receive a medal and official timing.

Tackle scenic singletrack along Otter Creek in Brandenburg, KY on Dec 20, 2025, with marathon, 16 mile and 8 mile options. Rolling hills, creekside trails, hot food and carved wooden medals make this a cozy winter trail challenge.

Join Race The Trails on April 4, 2026 in Newburgh, IN for scenic trail runs including Warrick County's first half marathon, a 5K and kids races. Celebrate new trails at Friedman Park while supporting local park improvements.

Knobstone 50 on April 11, 2026 is a point to point 50 mile trail race through rugged southern Indiana with roughly 10,000 feet of climbing along the Knobstone Trail. Registration closes April 3 and pacers are allowed for the 50 mile field.

Enjoy singletrack trail runs and mountain bike endurance races at Saunders Springs Nature Preserve with solo, duo and team classes plus kids races. Proceeds benefit local trail stewardship and KyMBA programs, so you can race and give back.

Join the 6th Annual Honor and Remember Run at Cool Springs in Velpen IN to salute veterans, first responders and 9/11 heroes. Choose 5K, 10K trail with a Ruck option or virtual entry and enjoy awards, refreshments and timed results.

Run scenic loops at Lincoln State Park with marathon, 14K or 5K options through woods and gravel. Aid stations, marathon drop bags and eco friendly finisher mementos make this a welcoming trail event.