Trail Running in Connecticut
Connecticut has 22 upcoming trail-running races scheduled for 2026. Cornwall is the busiest city with 12 races, ahead of Stratford (2) and Hebron (1). The list includes Iron Hike Ultra Series in Cornwall on October 1 — multi-day trail ultra series.
Showing all 22
Trail Running
Summer Solstice Trail Run
Hebron, CT
Trail Running
Summer Solstice Trail Run
June 20, 2026
Hebron, CT
Trail Running
Centurion Trail 33 Hour Ultra
Stratford, CT
Trail Running
Centurion Trail 33 Hour Ultra
June 30, 2026
Stratford, CT
Trail Running
17th Annual Farmington River Run 5K Trail Race
September 20, 2026
Farmington, CT
Trail Running
Moosup Valley 5k, 8K and 10K All Trail Race
Sterling, CT
Trail Running
Moosup Valley 5k, 8K and 10K All Trail Race
September 27, 2026
Sterling, CT
Trail Running
Iron Hike - Fall Everest / 29029 Everesting Ultra Trail Marathon - 61+ Miles | 29,029'+ Elevation | 72-Hour | Run, Hike or Walk
October 1, 2026
Cornwall, CT
Trail Running
Iron Hike - Fall Olympus Mons Ultra Trail Marathon - powered by Skratch Labs ® - 152+ Miles | 72,590' Elevation | 84-Hour | Run, Hike or Walk
October 1, 2026
Cornwall, CT
Trail Running
Iron Hike - Fall Everest / 29029 Everesting Ultra Trail Marathon Relay - 61+ Miles | 29,029'+ Elevation | 72-Hour | Run, Hike or Walk
October 1, 2026
Cornwall, CT
Trail Running
Iron Hike - Fall Answer the Bell Ultra Trail Marathon - Full (Backyard Ultra Format) - 100+ Miles | 50,400' Elevation | 84-Hour | Run, Hike or Walk
October 1, 2026
Cornwall, CT
Trail Running
Iron Hike - Fall Olympus Mons Ultra Trail Marathon Relay - powered by Skratch Labs ® - 152+ Miles | 72,590' Elevation | 84-Hour | Run, Hike or Walk
October 1, 2026
Cornwall, CT
Trail Running
Iron Hike - Fall Denali Ultra Trail Marathon - 43+ Miles | 20,825' Elevation | 48-Hour | Run, Hike or Walk
October 2, 2026
Cornwall, CT
Trail Running
Iron Hike - Fall Denali Ultra Trail Marathon Relay - 43+ Miles | 20,825' Elevation | 48-Hour | Run, Hike or Walk
October 2, 2026
Cornwall, CT
Trail Running
Iron Hike - Fall Answer the Bell Ultra Trail Marathon - Basic (Backyard Ultra Format) - 28+ Miles | 14,400'+ Elevation | 24-Hour | Run, Hike or Walk
October 3, 2026
Cornwall, CT
Trail Running
Iron Hike - Fall Double Kuwohi Trail Marathon Plus Relay - 28+ Miles | 13,685' Elevation | 24-Hour | Run, Hike or Walk
October 3, 2026
Cornwall, CT
Trail Running
Iron Hike - Fall Double Kuwohi Trail Marathon Plus - 28+ Miles | 13,685' Elevation | 24-Hour | Run, Hike or Walk
October 3, 2026
Cornwall, CT
Trail Running
Iron Hike - Fall Kuwohi Trail Half Marathon Plus - 15 Miles | 7,140' Elevation | 12-Hour | Run, Hike or Walk
October 3, 2026
Cornwall, CT
Trail Running
Iron Hike - Fall Kuwohi Trail Half Marathon Plus Relay - 15 Miles | 7,140' Elevation | 12-Hour | Run, Hike or Walk
October 3, 2026
Cornwall, CT
Trail Running
Norfolk Land Trust Trail Race Series/Haystack Mountain Challenge
October 4, 2026
Norfolk, CT
Trail Running
Cheshire Community YMCA Harvest Trail Race and Y Cup Relay
October 24, 2026
Cheshire, CT
Top Cities for Trail Running in Connecticut
Trail Running in Nearby States
Frequently asked questions
What is trail running?▾
Trail running takes place on unpaved surfaces like dirt paths, mountain trails, and forest roads. Distances range from 5K to 100+ miles. Trail running emphasizes scenery, elevation, and technical terrain over pace.
What shoes do I need for trail running?▾
Trail running shoes have aggressive lugs for traction, rock plates for protection, and a more durable outsole than road shoes. Popular brands include Hoka, Salomon, and Altra. Choose shoes based on your local terrain.
How is trail running different from road running?▾
Trail running involves more elevation change, uneven footing, and slower paces than road running. Expect to run 20-40% slower on trails compared to roads. The focus shifts from pace per mile to effort and time on feet.
What are the best trail running destinations in the US?▾
Colorado, California, Oregon, and Utah offer world-class trail running. Iconic areas include the Sierra Nevada, Rocky Mountains, Pacific Northwest forests, and Appalachian trails. Browse trail events by state on RACE.