Pittsburgh
Trail Running Calendar near Pittsburgh 2026-2027
Explore the top trail runs near Pittsburgh for 2026-2027! We've gathered 31 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
A Hawaiian-themed 5K obstacle course with a team pineapple rule, family play zone and a post-race luau that raises funds for blood cancer research and Lending Hearts.
Eighth Annual Tuff Tornado Run at Alameda Park is a two mile, 22 obstacle mud run with chip timing, food trucks, music, and fundraising for school programs.
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.
A six hour timed trail event at Brady's Run Park on a 2.1 mile loop featuring steep opening climbs, ridgeline single track and technical switchback descents. Open to solo runners and two person relay teams with awards for top finishers.
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.
A Friday evening 5K through tree-lined Riverview Park around Observatory Hill with a hilly course, a costume contest, and fall family activities.
A memorial 5K run and walk in Greensburg on October 10, 2026 hosted by Westmoreland Christian Academy with proceeds supporting a local scholarship fund.
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.
A hilly 5K at Veteran's Park on 10/11/2026 with custom socks and chili for finishers, age-bracket medals, and a family festival with vendors and activities.
Trail event in Allison Park, PA on October 17, 2026 featuring a 5 mile trail race and a free children's fun run for the event's 20th anniversary.
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.