Chesterfield
Trail Running Calendar near Chesterfield 2026-2027
Explore the top trail runs near Chesterfield for 2026-2027! We've gathered 41 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
December 2026
A winter trail run series at Rockwoods Reservation across three dates, offering varied routes, chip timing, finisher medals, shirts and live course tracking.
January 2027
A 5K trail race at Cliff Cave County Park in St. Louis featuring a mixed pavement and dirt-loop course, a cup-free policy, inclusivity measures, and on-site registration.
Winter trail event at Creve Coeur Park offering 1 mile, 5K, 10K and a half marathon with shirts, medals, hot drinks and proceeds benefiting the Crohn's and Colitis Foundation.
A winter trail run series at Rockwoods Reservation across three dates, offering varied routes, chip timing, finisher medals, shirts and live course tracking.
A Midwest winter ultramarathon in Missouri on January 16 and 17 2027 offering multiple trail distances from 20 miles to 100 miles, including a night 40 miler. The event is managed by PR Racing and alternates course direction by year.
Castlewood Cup is a 15 km trail race at Indian Camp Creek Park on January 30, 2027, with post-race BBQ, beer for 21+, and live music when weather allows.
February 2027
Night trail event on a 4.2 mile single track loop in Greensfelder County Park, with 9 hour, 6 hour, and 3 hour timed options.
Winter trail event at Rockwoods Reservation in Glencoe Missouri offering a 5 Mile and a 13.1 Mile course. Organized by Rockinator Racing as the Stick Season finale with chip timing, aid stations, on course tracking and post race awards.
A winter trail run series at Rockwoods Reservation across three dates, offering varied routes, chip timing, finisher medals, shirts and live course tracking.
March 2027
Queeny Backyard Ultra on March 5, 2027 is a last person standing trail event at Queeny Park on a roughly 4.19 mile loop repeated hourly. The overall winner earns a guaranteed Silver Ticket entry within the mid August 2026 to mid August 2027 window.
April 2027
Multi day trail running event in Wildwood MO with distances from a kids mile up to 100 miles and a Night 50K.
A three day stage race in western St Louis County with multi stage distances over rugged trails, creek crossings and scenic bluffs.
May 2027
Road and trail runs through Augusta wine country with 1 mile, 5K, 10K and a half marathon plus a wine passport, awards and post-race festivities.
A 5K, 10K and half marathon along the Katy Trail and Frontier Park in historic downtown St Charles, with post race awards and a festival style finish area.
June 2027
A family friendly 5K obstacle run at Brookdale Farms on June 5, 2027 with Adult and KIDZ Family waves; participants must bring a signed waiver and adults need photo ID.
Gather a team for an 82 mile relay from St. Louis to Hermann featuring the scenic Katy Trail and Missouri wine country.
Baby Shippey is a summer trail race at Beaumont offering a rugged 10k and a 13.05 mile half with steep climbs, rock traverses and aid stations. Entry is limited to the first 150 runners.
July 2027
Rockin' Riverfest on July 3, 2027 at Frontier Park in St Charles offers 5K, 10K, a 5K Fun Run Walk and a 13.1 miles half along the Katy Trail and riverside single track with on course aid stations and race amenities.