Westfield close

Trail Running Calendar near Westfield 2026-2027

Header image

Explore the top trail runs near Westfield for 2026-2027! We've gathered 12 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

August 2026
Aug
15
Sa

Shenipsit Striders Fatass

Trail Run 3 mi
A free 8-hour trail event in Tolland, CT where runners complete as many 3-mile loops on a marked 5K-ish course as they like, with provided food and a potluck.
Aug
15
Sa

Brimfield Wine Run 5K

Trail Run 2 mi 5 km
A chip-timed 5K run/walk at Brimfield Winery on a two-lap grass course with hills, race swag, a wine pour, and age group awards; a one-lap 1.5 mile division is available.
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
20
Su

Farmington River Run 5K Trail Race

Trail Run 5 km
A 5K trail run at Winding Trails in Farmington on the designated course around Walton Pond, with registration from February 20 to September 20 and a $35 fee; overall and age-group awards plus a prize for the first local finishers.
Sep
26
Sa

Tunxis Trail Ultramarathon

Trail Run 5 km 8 km
Technical trail races in Burlington CT on the Tunxis Trail offering 8K and 5K courses that pass the CT State Trout Hatchery and Nassahegan State Forest.
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.
Add Event
Help us complete the calendar!
  • Distance is at least 5 km
  • Event has a website or Facebook page
Website
Optional: Please provide your e-mail address if we may contact you.
Report a change
We will only update the data if the information is also on the website.