Boston
Trail Running Calendar near Boston 2026-2027
Explore the top trail runs near Boston for 2026-2027! We've gathered 24 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
Run or walk a 5k on the Gap Trail to kick off the West Newton River Festival featuring live music, food, and fireworks.
A six hour loop challenge on shaded single track trails in North Park near Deer Browse 2 Pavilion in Allison Park PA. Runners complete as many 2 mile loops as they wish, earn a raffle ticket per loop, and top male and female loopers receive awards.
A Hawaiian themed 5K obstacle race at Allegheny RiverTrail Park in Aspinwall that raises funds for The Stanley M. Marks Blood Cancer Research Fund and Lending Hearts. Teams carry a pineapple through the course and a luau follows with live music, food..
October 2026
Fineview Step Challenge in Pittsburgh on October 3, 2026 features 2 mile and 5 mile courses that climb 12 public staircases with over 1,600 steps including a 371 step set on Rising Main Avenue. Proceeds support Fineview Citizens Council programming.
Chip timed 5K through Thistlethwaite Vineyards in Jefferson PA on October 3 2026, with race swag, a wine pour, and age group awards.
Experience a classic cross country race on the trails of North Park during the autumn foliage season. Enjoy 20k, 10k, and 5k distances featuring handmade bamboo medals and traditional folk dancing.
An evening 5K through hilly, tree lined Riverview Park in Pittsburgh with a youth costume contest, seasonal family activities, and limited shirts for the first 200 registrants.
A community 5K run and walk on the Five Star Trail in Greensburg, PA, held October 10, 2026, with a mostly flat course and proceeds supporting a memorial scholarship fund for local Christian education.
Community race in Schenley Park with a 5 km adult course, 1 km kids loop, packet pickup, picnic, and a finishers' medal shaped like the republic.
Celebrate the 20th anniversary of the Dirt Monster Trail Fest with 5 mile races through the rugged forest hills and scenic trails of Allison Park Pennsylvania.
November 2026
Trail races at Settlers Cabin Park on November 14, 2026 offering 5K, 8 Mile, 25K and 50K distances on wooded trails with aid stations and memorial sections.
15th Annual Seneca Valley Cross Country Turkey Chase is a USATF-certified 5K at Graham Park with age-group awards and food donations collected for Armstrong's Breaking Bread Initiative.
December 2026
A holiday themed event in Oakdale with a flat out and back 5K on the Panhandle trail and an untimed 1 mile fun walk. Awards include finisher medals, top overall and age group prizes, with holiday merchandise while supplies last.
April 2027
A family friendly endurance event in Allison Park with multi-loop ruck, run and walk options on 4.7 mile trails and a 2.2 mile pavement adaptive loop.
Looped trail races at Settlers Cabin Park on April 18, 2027 offering 50K, 25K, 8 Miler, and 5K over mostly wooded, technical trails.