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Trail Running Calendar near Glenshaw 2026-2027

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Explore the top trail runs near Glenshaw for 2026-2027! We've gathered 25 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

August 2026
Obstacle course events in Zelienople on August 23, 2026, featuring a 1.2 to 1.5 mile loop race, age-group challenges, awards, and a multi-day kids camp.
A point-to-point 50-mile ultramarathon on the Baker Trail with 6,200 feet of climbing, individual and five-person relay options, and wayfinding via yellow blazes.
A community road event on August 30, 2026 at McCahill Park in Pittsburgh with a 5K and a 1 Mile race; every finisher receives a medal and t-shirts are available as an add-on.
September 2026
A family friendly 5K mud run at Switchback MX on September 5, 2026 with obstacles, mud pits, an on‑site festival and VIP and value registration options.
Trail races of 13.1 miles, 20 miles, and 50K through Montour Woods with aid stations, finisher medals, and proceeds to Hollow Oak Land Trust.
A 24 hour 10K loop challenge at Moraine State Park on September 11 to 12, 2026, with laps across Pleasant Valley, Hilltop and Sunken Garden trails.
A 5K run and a 5K walk along the Gap Trail in West Newton, PA on 09/12/2026, held as part of the town's river festival with food, crafts, games, live music 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..
A community 5K run and walk in Leechburg that follows mixed pavement and trail and crosses the Kiskiminetas River. Proceeds benefit The Breast Cancer Research Foundation.
Two mile obstacle run at Alameda Park on September 26, 2026 featuring twenty two obstacles including a mud pit, foam run and car wash. Proceeds support local Butler Area School District programs.
October 2026
A 104-mile out-and-back trail race near Export, PA, covering Westmoreland Heritage and West Penn trails with 7,392 ft gain and staffed aid stations.
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 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.
Trail running event in Allison Park, PA on October 17, 2026 with 5 miles, 25K and a Little Monsters run over wooded, hilly trails and pace-grouped entries with separate fees.
Experience a Halloween themed trail race through the scenic woods of North Park. Choose between the 6.66K or 13K distances and enjoy a festive atmosphere in Allison Park.
November 2026
A trail race day at Raccoon Creek State Park on 11 July 2026, featuring distances from 1 mile to 50K, aid stations on longer routes, and fundraising in support of a veteran community care organization.
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