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Trail Running Calendar near Union 2026-2027

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Explore the top trail runs near Union for 2026-2027! We've gathered 13 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.
Aug
23
Su

Old Goat Track Club XC Classic

Trail Run 5 km
A 5K cross country race at Waters Farm in Sutton Massachusetts that opens the USATF New England XC Grand Prix series. Separate men's and women's open races, on site registration, and a post race awards ceremony.
September 2026
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
19
Sa

PCS Harvest Hustle 5K

Trail Run 5 km
A community fundraiser in Pomfret Center with a trail 5K and a 0.5 mile kids run supporting the Pomfret Community School PTO. Early and later registration fees differ and awards plus finisher medals are given.
Sep
27
Su

Moosup Valley 10K All Trail Race

Trail Run 5 km 8 km 10 km
A trail event on the Moosup Valley State Park Trail featuring 5K, 8K, 10K and a Kids Fun Run. Parking and the finish are at Weidele's Pizza with post-race food, awards and a medallion or shirt option.
October 2026
Oct
4
Su

Nipmuck Trail Marathon

Trail Run 26 mi
A 26.4 mile trail marathon in Ashford, CT on October 4, 2026 with rugged terrain and a two-person relay option.
Oct
17
Sa

Tackle the Trail - Pomfret, CT

Trail Run 6 mi 13 mi 26 mi
Experience a point to point trail race in Northeast Connecticut on the Airline Trail. Choose between marathon, half marathon, and 10K distances with individual or relay team options to support local student education.
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.
Oct
24-25
Sa - Su

Dead Last Ultra

Trail Run Backyard Ultra Walk 4 mi
Backyard ultramarathon at Waters Farm with a 4.167 mile hourly loop, a 4.2 mile community run, a free kids fun run, and a full festival.
November 2026
Nov
8
Su

Thompson Turkey Trot

Trail Run 5 km
A family friendly run and walk at West Thompson Dam on November 8, 2026 featuring a timed 5K trail run, a 3K untimed walk and a free kids 1/4 mile run; proceeds support local trails, parks and a food pantry.
March 2027
Mar
28
Su

Northern Nipmuck Trail Race

Trail Run 16 mi
A roughly 16 mile out and back on the Nipmuck Trail in Union CT with minimal aid stations, blue blazes, and proceeds supporting local trail stewardship.
April 2027
Apr
3
Sa

Run Across CT

Trail Run 100 mi 123 mi
A point to point 123 mile ultramarathon across Connecticut on April 3, 2027, featuring trail and road sections, aid stations, five intermediate cutoffs and a 36 hour limit.
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