Trail Running calendar near Chester 2026-2027
We have found 130 Trailruns within 80 miles of Chester. See below where and when you can find the races.
0 – 100∞ km
Articles
Belgian Ultrarunner Karel Sabbe's Record-Breaking Pacific Crest Trail Run Showcased in New YouTube Documentary
Explore Karel Sabbe's record-breaking Pacific Crest Trail run in a riveting documentary. Jour..
Trail Running: How it Can Help Reduce Stress and Anxiety
Trail running is an effective way to reduce stress, anxiety, and improve physical and mental he..
Trail Running vs. Road Running: Which One Is Right For You?
When it comes to running, there are two primary options to choose from: trail running and road..
A 5K trail run in Hanover New Hampshire held on Mother’s Day, featuring packed trails, open fields and mellow single track. Pre registration is online only and race day registration is available with different fees by age group.
A dirt road 50k in Leyden, Massachusetts on May 16, 2026, with 4,200 feet of elevation change and a course that passes through forests, fields, and an 1870s covered bridge. Registration closes May 13 and there is no race-day entry.
A 5 km cross-country event at Canterbury Shaker Village on May 16, 2026 with in-person and virtual options. Online registration closes May 15 at 12:00 noon ET and the registration fee is $25.
A 50-mile point to point ultramarathon from Manchester to Mount Monadnock with about 6000 feet of gain over roads, dirt roads and trails. The course is GPX only with minimal markings, five aid stations, and a 125-runner cap.
Run or walk a 5k on the Southern New England Trunkline Trail in Franklin. This event supports the development of an abandoned rail bed into a multi use path connecting local communities.
Wason Pond Wrangler is an obstacle race on May 16, 2026 in Chester, New Hampshire, featuring a 5 km course run in multiple waves including a competitive wave. Online registration is closed and the event is limited to 800 participants.
A 25th annual cross country event in Newburyport, MA on May 17, 2026 with adult and youth 3 mile races plus a kids 1/2 mile. First 250 3 mile registrants receive shirts and race day donations support the Travis Landreth Scholarship Fund.
A 5K Fun Run at Strongwater Farm in Tewksbury on May 17, 2026 to raise funds for programs supporting people with mobility challenges. The trail course crosses corn fields and woods, with a shorter accessible route and family activities on s..
A two-day 4K race on Cathleen Stone Island in Boston Harbor with individual and team entries, a short ferry ride, chip timing, and an on-island finish with dinner and beer. Funds raised support hands on science programs for Boston youth.
A Memorial Day Weekend inaugural *5k* trail run through Groton's General Field on May 24, 2026. The event supports Operation Delta Dog, which rescues and trains service dogs for veterans.
A 5K trail event on May 30, 2026 at Danvers YMCA Camp in Boxford with separate courses for runners and for walkers and waggers, pond and vernal pool scenery, prizes, post-race treats, and registration benefits.
Operation Mohawk Tactical 2 in Foxboro, MA offers 4, 5, and 9 mile running and rucking options. The event honors fallen service members and supports veteran and first responder suicide prevention under the mission of 22Mohawks.
Test your endurance at the Ascutney Mountain Run in Vermont. This 3.7 mile uphill race climbs 2,300 vertical feet along a paved auto road to a scenic mountain summit finish.
Run of The Fellowship is an in-person trail event at Clifford Park in Biddeford, Maine on May 30, 2026. It offers a 5K route and a longer full quest option, welcomes costumes, and is pending final permits and insurance.
On May 31, 2026 at Ice House Park in Woburn, MA the second annual Live Free Fun Run and Festival pairs a scenic *2.5 mile* off-road run or walk with a community festival. The festival features food trucks, a DJ, activities and tables from l..