Upcoming Races Near Cheshire, CT - Matching: Trail Races

Name: Frosty Forest 5k
Start: 2026-12-19
End: 2026-12-19
Location: Stratford

King of The Hill

Kings Park, NY

Saturday, March 7th, 2026

Featured

Trail

View details for race King of The Hill

Want to feature your race?

Get your race seen first by thousands of runners

Learn More

Learn how to feature your race

SRC & Friends Supported Long Run

Wading River, NY

Sunday, March 15th, 2026

15K

Ultra

Trail

View details for race SRC & Friends Supported Long Run

Run For The Shamrock

Hamden, CT

Sunday, March 15th, 2026

Trail

View details for race Run For The Shamrock

Enchanted Forest Ultra Run

Stratford, CT

Saturday, March 21st, 2026

Trail

View details for race Enchanted Forest Ultra Run

ANDREW'S TOP GUN RUN 5K

Calverton, NY

Saturday, March 28th, 2026

Trail

Fast

View details for race ANDREW'S TOP GUN RUN 5K

Mudders and Grunters

Yorktown Heights, NY

Sunday, March 29th, 2026

Trail

View details for race Mudders and Grunters

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

John Jay Community Trail Race

Cross River, NY

Sunday, April 12th, 2026

Trail

View details for race John Jay Community 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

Brookhaven Trail 15K and 4 Mile Trail Run

Wading River, NY

Sunday, April 19th, 2026

15K

Trail

View details for race Brookhaven Trail 15K and 4 Mile Trail Run

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

Leatherman's Loop

Cross River, NY

Sunday, April 26th, 2026

10K

Trail

View details for race Leatherman's Loop

Try the Trail

Katonah, NY

Sunday, April 26th, 2026

1 Mile

Trail

View details for race Try the Trail

CTA Scholarship 5k Run/Walk

Carmel, NY

Sunday, May 3rd, 2026

Trail

View details for race CTA Scholarship 5k Run/Walk

Mount Archer Trail Race

Lyme, CT

Sunday, May 3rd, 2026

Trail

Fast

View details for race Mount Archer Trail Race

Forgotten Forest 9 Hour Ultra

Stratford, CT

Saturday, May 16th, 2026

Trail

View details for race Forgotten Forest 9 Hour Ultra

Spring Run The Farm

Katonah, NY

Sunday, May 17th, 2026

1 Mile

Trail

View details for race Spring Run The Farm

Run the Vineyards - Memorial Day at Pindar 5K

Peconic, NY

Sunday, May 24th, 2026

1 Mile

Trail

View details for race Run the Vineyards - Memorial Day at Pindar 5K

Oh Boy 5K

Waterbury, CT

Monday, May 25th, 2026

Trail

View details for race Oh Boy 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

Hamden Fest Half Marathon & 5k

Hamden, CT

Saturday, June 6th, 2026

Half

Trail

View details for race Hamden Fest Half Marathon & 5k

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

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

Centurion Trail 33 Hour Ultra

Stratford, CT

Saturday, June 27th, 2026

Trail

View details for race Centurion Trail 33 Hour Ultra

Run the Vineyards - Pindar Vineyards 5K

Peconic, NY

Sunday, July 26th, 2026

Trail

View details for race Run the Vineyards - Pindar Vineyards 5K

Run for The Hills

Niantic, CT

Saturday, September 5th, 2026

Trail

View details for race Run for The Hills

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

Forbidden Forest 30 Hour Ultra

Stratford, CT

Saturday, October 3rd, 2026

Trail

View details for race Forbidden Forest 30 Hour Ultra

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

Ivoryton Pumpkin Chase

Ivoryton, CT

Saturday, October 24th, 2026

Trail

View details for race Ivoryton Pumpkin Chase

FALL Run The Farm

Katonah, NY

Sunday, October 25th, 2026

1 Mile

Trail

View details for race FALL Run The Farm

Raven Events

Cross River, NY

Sunday, November 1st, 2026

10K

Trail

View details for race Raven Events

Storybook Half Marathon

Stratford, CT

Saturday, November 21st, 2026

Half

Trail

View details for race Storybook Half Marathon

Frosty Forest 5k

Stratford, CT

Saturday, December 19th, 2026

Trail

View details for race Frosty Forest 5k

Explore more in Cheshire, CT

Distances:

5K 10K Half Marathon Marathon

Months:

January February March

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Connecticut races

Don't see your race? Add it!

Add Your Race (Free)