Upcoming Races Near Winsted, CT - Matching: Trail Races

Name: Tom Centinaro Memorial "Dam" Race
Start: 2026-10-17
End: 2026-10-17
Location: Wolcott

Run For The Shamrock

Hamden, CT

Sunday, March 15th, 2026

Featured

Trail

View details for race Run For The Shamrock

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Sparrow's Nest Superhero Rock 'N' Run Challenge...

Poughquag, NY

Monday, March 30th, 2026

Ultra

Trail

View details for race Sparrow's Nest Superhero Rock 'N' Run Challenge and 5K

Hoppin Hodges Rails to Trails 5K

Andover, CT

Sunday, April 5th, 2026

Trail

View details for race Hoppin Hodges Rails to Trails 5K

Joseph Ennesser 5K Run/Walk

Wappingers Falls, NY

Saturday, April 11th, 2026

Trail

View details for race Joseph Ennesser 5K Run/Walk

11th Annual F.O.R 5k Trail Race

Wilbraham, MA

Sunday, April 12th, 2026

Trail

View details for race 11th Annual F.O.R 5k Trail Race

Ion Bank Cheshire Road Races

Cheshire, CT

Sunday, April 12th, 2026

Half

Trail

Fast

View details for race Ion Bank Cheshire Road Races

Tommy Sullivan's 5K

Branford, CT

Sunday, April 19th, 2026

Trail

View details for race Tommy Sullivan's 5K

2026 Deer Lake 5 Mile Trail Run

Killingworth, CT

Sunday, April 26th, 2026

Trail

View details for race 2026 Deer Lake 5 Mile Trail Run

Seven Sisters Trail Race Charity Bibs

Amherst, MA

Saturday, May 2nd, 2026

Trail

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Dandelion Dash and Mushroom Mile

Hadley, MA

Sunday, May 3rd, 2026

1 Mile

Trail

View details for race Dandelion Dash and Mushroom Mile

CTA Scholarship 5k Run/Walk

Carmel, NY

Sunday, May 3rd, 2026

Trail

View details for race CTA Scholarship 5k Run/Walk

Sgt. Joshua D. Desforges Walk/Run Challenge

Ludlow, MA

Saturday, May 9th, 2026

Trail

View details for race Sgt. Joshua D. Desforges Walk/Run Challenge

Oh Boy 5K

Waterbury, CT

Monday, May 25th, 2026

Trail

View details for race Oh Boy 5K

Peach Hill "Run For the Hill of It" 5K

Poughkeepsie, NY

Saturday, May 30th, 2026

Trail

View details for race Peach Hill "Run For the Hill of It" 5K

IronHike Endurance Series - Spring 2026 - Mohaw...

Cornwall, CT

Wednesday, June 3rd, 2026

Ultra

Trail

View details for race IronHike Endurance Series - Spring 2026 - Mohawk Mtn, CT, USA

IronHike Series - Spring '26

Mohawk Mtn Ski Area, Cornwall, CT

Thursday, June 4th, 2026

Ultra

Trail

View details for race IronHike Series - Spring '26

Iron Hike - Spring Kuwohi Trail Half Marathon P...

Cornwall, CT

Saturday, June 6th, 2026

Trail

View details for race Iron Hike - Spring Kuwohi Trail Half Marathon Plus - 15 Miles | 7,140' Elevation | 12-Hour | Run, Hike or Walk

Hamden Fest Half Marathon & 5k

Hamden, CT

Saturday, June 6th, 2026

Half

Trail

View details for race Hamden Fest Half Marathon & 5k

Run in the Park 5K - to benefit the Milford Rot...

Milford, CT

Sunday, June 7th, 2026

Trail

View details for race Run in the Park 5K - to benefit the Milford Rotary and the Beth-El Center

Smile Like Jack 5k/10k/Fun Run

East Otis, MA

Saturday, July 11th, 2026

10K

Trail

View details for race Smile Like Jack 5k/10k/Fun Run

Where the Pavement Ends Single & Double Loop

Ridgefield, CT

Sunday, September 20th, 2026

Trail

View details for race Where the Pavement Ends Single & Double Loop

IronHike Series - Fall '26

Mohawk Mtn Ski Area, Cornwall, CT

Thursday, October 1st, 2026

Ultra

Trail

View details for race IronHike Series - Fall '26

Run Stanley

Westfield, MA

Sunday, October 4th, 2026

1 Mile

Trail

View details for race Run Stanley

Tom Centinaro Memorial "Dam" Race

Wolcott, CT

Saturday, October 17th, 2026

Trail

View details for race Tom Centinaro Memorial "Dam" Race

Explore more in Winsted, CT

Distances:

5K 10K Half Marathon Marathon

Months:

February March April

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Connecticut races

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