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Trail Running Calendar near Huntington 2026-2027

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Explore the top trail runs near Huntington for 2026-2027! We've gathered 10 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

August 2026
Aug
22
Sa

Jug End Loop Ultra

Trail Run Walk 4 mi
A timed six hour loop event on Aug 22, 2026 at Jug End State Reservation in Egremont MA with repeated 4.2 mile laps and a 0.75 mile final loop.
September 2026
Sep
5
Sa

Run the Dam for Davenport

Road Race Trail Run Walk 5 km
Charity 5K run and 1.5 mile walk in Huntington MA on a mixed pavement, field and trail course that finishes at Littleville Dam.
Sep
12
Sa

Cross-Connecticut Run for Mental Health Awareness

Trail Run 56 mi
A 56 mile end to end run along the Farmington Canal Heritage Trail from West Suffield to New Haven raising funds for Mental Health Connecticut.
Sep
12
Sa

Free to Run Trail Races - Pittsfield, MA

Trail Run 5 mi 15 km ... 25 km 50 km
September 12, 2026 trail races in Pittsfield State Forest offering 50K, 25K, 15K and a new 5 mile option with proceeds supporting Free to Run.
October 2026
Oct
4
Su

Run Stanley

Trail Run Walk 5 km
Join the annual Run Stanley event at Stanley Park for a variety of trail races including a 5K K9 run and an accessible 1 mile stroll. Support local wildlife sanctuary maintenance while enjoying a community day in the park.
Oct
4
Su

Norfolk Land Trust Trail Race Series

Trail Run 5 km 10 km 13 mi
A fall trail race day in Norfolk, CT offering 5K, 10K and a half marathon with steep climbs, private-trail sections, a cupless policy with water stations, and on-site food and beverage vendors.
Oct
24
Sa

Mt. Tom Trail Race

Trail Run Walk 5 km 10 km 25 km
A fall trail race at Mt. Tom State Park on October 24, 2026, with single and relay options from 5k to 25k on rugged single-track terrain. The event supports Kestrel Land Trust and includes aid stations, medical crews, and awards.
November 2026
Nov
1
Su

Kevin Hutt 10k

Trail Run 10 km
Trail 10K in Bloomfield CT on Nov 1, 2026 honoring Kevin Hutt, run on rocky single track in Penwood State Park with proceeds partly to NAMI.
April 2027
Apr
17
Sa

Traprock 50

Trail Run 17 km 50 km
Trail event in Bloomfield CT with 17K and 50K loop courses featuring technical Metacomet Trail single track and rocky forest terrain.
June 2027
Jun
4-6
Fr - Su

Connecticut Ultra Traverse (CUT112)

Trail Run 50 mi 112 mi
Point-to-point trail runs of 112 or 50 miles along the New England Trail blue blazes to Guilford, CT, requiring dedicated crews, navigation, and night trail experience.
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