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Upcoming Races Near Woodstock, CT - Matching: Trail Races

Ivoryton Pumpkin Chase

Ivoryton, CT

Saturday, October 18th, 2025

Featured

5K

Trail

View details for race Ivoryton Pumpkin Chase

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Pumpkin Pacer 5k @ White Barn Farm

Wrentham, MA

Saturday, October 25th, 2025

5K

Trail

View details for race Pumpkin Pacer 5k @ White Barn Farm

Powisset Farm Trail Run - Fall

Dover, MA

Sunday, October 26th, 2025

5K

1 Mile

Trail

View details for race Powisset Farm Trail Run - Fall

Run for the Hills

Harvard, MA

Sunday, October 26th, 2025

5K

1 Mile

Trail

View details for race Run for the Hills

Haunted Hustle

Waterford, CT

Sunday, October 26th, 2025

5K

1 Mile

Trail

View details for race Haunted Hustle

Pawtuxet River 5k: Run of the Mills

Coventry, RI

Saturday, November 1st, 2025

5K

Trail

View details for race Pawtuxet River 5k: Run of the Mills

21st Annual GFRC Busa Bushwhack Trail Races

Framingham, MA

Sunday, November 2nd, 2025

10 Miles

Trail

View details for race 21st Annual GFRC Busa Bushwhack Trail Races

Stonington Vineyards Wine Run Turkey Trot 5k

Stonington, CT

Sunday, November 2nd, 2025

5K

Trail

View details for race Stonington Vineyards Wine Run Turkey Trot 5k

2025 Upton 10.5K and Half Marathon Trail Race

Upton, MA

Sunday, November 9th, 2025

10K

Trail

View details for race 2025 Upton 10.5K and Half Marathon Trail Race

Centerville Bank Thompson Turkey Trot

Thompson, CT

Sunday, November 9th, 2025

5K

Trail

View details for race Centerville Bank Thompson Turkey Trot

Upton 10.5K and Half Marathon Trail Race

Upton, MA

Sunday, November 9th, 2025

Half

Trail

View details for race Upton 10.5K and Half Marathon Trail Race

The Baystate Dirty Dog Trail Run-Ruck-Walk 5k

Berkley, MA

Sunday, November 16th, 2025

5K

Trail

View details for race The Baystate Dirty Dog Trail Run-Ruck-Walk 5k

F.I.T. Turkey Trot TRAIL Race

Cumberland, RI

Thursday, November 27th, 2025

Trail

View details for race F.I.T. Turkey Trot TRAIL Race

Dandelion Dash and Mushroom Mile

Hadley, MA

Sunday, May 3rd, 2026

5K

1 Mile

Trail

View details for race Dandelion Dash and Mushroom Mile

Run for The Hills

Niantic, CT

Saturday, September 12th, 2026

5K

Trail

View details for race Run for The Hills

Explore more in Woodstock, CT

Distances:

5K 10K Half Marathon Marathon

Months:

October November December

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Connecticut races

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