Happy Valley
Trail Running Calendar near Happy Valley 2026-2027
Explore the top trail runs near Happy Valley for 2026-2027! We've gathered 22 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
A low-key series of Wednesday evening trail races in Portland's Forest Park with three five-race Series April to October, 4 to 7 mile hilly courses and Series standings.
Point to point 50K on the Pacific Crest Trail from Stabler to North Bonneville with a summit detour to Three Corner Rock and varied trail terrain.
A low-key series of Wednesday evening trail races in Portland's Forest Park with three five-race Series April to October, 4 to 7 mile hilly courses and Series standings.
A 3.1 mile obstacle run with 22 symbolic obstacles raising funds and awareness for organizations that combat human trafficking and support survivors.
Four-race cross country series in Portland parks from Sept 26 to Nov 7 2026 with separate men and women races and USATF championship events.
A low-key series of Wednesday evening trail races in Portland's Forest Park with three five-race Series April to October, 4 to 7 mile hilly courses and Series standings.
October 2026
A last person standing trail race on Hamilton Island in the Columbia River Gorge where runners repeat a 4.13 mile loop each hour and must finish each loop in under 60 minutes to continue until one runner remains.
In-person event in Gresham on October 4, 2026 with a 5K, a kids dash for ages eight and under, and a virtual run option.
A community 5K in Milwaukie on October 10, 2026, with a mostly paved flat course, shirt and medal for registrants, and proceeds supporting local nonprofits.
A low-key series of Wednesday evening trail races in Portland's Forest Park with three five-race Series April to October, 4 to 7 mile hilly courses and Series standings.
A looped ultramarathon in St. Paul OR with 10 km loops and options for 50 mile, 50K, 30K plus a free 1K kids run.
A Halloween-themed race day at Pacific Community Park featuring youth and community 2k–5k courses on grass and compact trail, with medals and holiday prizes.
A low-key series of Wednesday evening trail races in Portland's Forest Park with three five-race Series April to October, 4 to 7 mile hilly courses and Series standings.
November 2026
Trail event at Mary S. Young Park November 26 to 29, 2026 featuring a roughly 3.8 miles trail, a half mile kids trot and a virtual option.
December 2026
June 2027
A chip timed 5k at Helvetia Vineyards with a scenic but hilly vineyard course, a postrace wine pour, age group awards, and support for the Nik’s Wish charity.