Upcoming Races Near Winsted, CT

Name: Brookfield Lions Run for Sight 4-Miler
Start: 2026-01-01
End: 2026-01-01
Location: Brookfield

Hillacious Half Marathon

Litchfield, CT

Saturday, November 15th, 2025

Featured

Half

10K

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Glastonbury River Runners Race To Fill the Pantry

Glastonbury, CT

Sunday, November 16th, 2025

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Roadtown Turkey Trot 5k

Shutesbury, MA

Saturday, November 22nd, 2025

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Fischang-Cicchetti Memorial Road Race

Waterbury, CT

Sunday, November 23rd, 2025

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Run for the Turkeys 5K Road Race

New Fairfield, CT

Sunday, November 23rd, 2025

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Cleats on the Streets 5K

Windsor, CT

Sunday, November 23rd, 2025

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Boys & Girls Club of Ridgefield 44th Annual Tur...

Ridgefield, CT

Thursday, November 27th, 2025

1 Mile

View details for race Boys & Girls Club of Ridgefield 44th Annual Turkey Trot

Falcon 5K Turkey Trot

Avon, CT

Thursday, November 27th, 2025

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Bethel Turkey Trot

Bethel, CT

Thursday, November 27th, 2025

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Rhinebeck Ferncliff Forest 5k Turkey Trot

Rhinebeck, NY

Thursday, November 27th, 2025

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Branford Thanksgiving 5K

Branford, CT

Thursday, November 27th, 2025

Fast

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Mid Hudson Road Runner's Club Annual Turkey Trot

Lagrangeville, NY

Thursday, November 27th, 2025

1 Mile

View details for race Mid Hudson Road Runner's Club Annual Turkey Trot

14th Annual O'BRiley 5K Turkey Trot AT 9AM

Collinsville, CT

Thursday, November 27th, 2025

View details for race 14th Annual O'BRiley 5K Turkey Trot AT 9AM

14th Annual Stuffing the Pantry 5k Run/Walk

East Longmeadow, MA

Thursday, November 27th, 2025

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Give 'Em the Bird 5k Run / 2K Walk (11th Annual)

Easthampton, MA

Thursday, November 27th, 2025

Trail

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Turkey Trot

Adams, MA

Thursday, November 27th, 2025

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Soul n Body Thanksgiving 5k

Wolcott, CT

Thursday, November 27th, 2025

Trail

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Run Turkey Run! Thanksgiving Day 5K

Hamden, CT

Thursday, November 27th, 2025

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Web Hill PTO Turkey Trot 2025

West Hartford, CT

Thursday, November 27th, 2025

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2025 Southbury Turkey Trot 5K & Kids Fun Run

Southbury, CT

Thursday, November 27th, 2025

Fast

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Commodore Hull Thanksgiving Day 5k Road Race

Shelton, CT

Thursday, November 27th, 2025

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Newtown Turkey Trot

Newtown, CT

Thursday, November 27th, 2025

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The Joyce Allen Great Turkey Escape

Redding, CT

Thursday, November 27th, 2025

1 Mile

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Run Like Kat

Longmeadow, MA

Friday, November 28th, 2025

1 Mile

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Fleet Feet Poughkeepsie's 2024 Grateful Gallop ...

Lagrangeville, NY

Saturday, November 29th, 2025

View details for race Fleet Feet Poughkeepsie's 2024 Grateful Gallop 5K to Benefit Dutchess Outreach

Candy Cane Sprint 2.5 Miler

Columbia, CT

Saturday, November 29th, 2025

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Cow Chip Cross Country Run for the 33rd year!

Trumbull, CT

Saturday, November 29th, 2025

View details for race Cow Chip Cross Country Run for the 33rd year!

Wolf Swamp Turkey Trot 5K Run/Walk

Longmeadow, MA

Saturday, November 29th, 2025

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The ODO Gobbler Run & Ruck

South Glastonbury, CT

Saturday, November 29th, 2025

1 Mile

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Run Santa Run

New Milford, CT

Saturday, November 29th, 2025

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2025 Durham Fall 4K Race

Durham, CT

Saturday, November 29th, 2025

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Donut Dash for Dana Farber

Willington, CT

Sunday, November 30th, 2025

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Pete Sanfilippo 44th Annual Holiday Run

Wappingers Falls, NY

Saturday, December 6th, 2025

1 Mile

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Woodburrr (no Y) 1-Miler

Woodbury, CT

Saturday, December 6th, 2025

1 Mile

Trail

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Santa Made Me Do It

Bethlehem, CT

Saturday, December 6th, 2025

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2025 NIA Jingle Bell Run - 37th Annual

Trumbull, CT

Saturday, December 6th, 2025

1 Mile

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YMCA 41st Annual Reindeer Ramble

Kingston, NY

Sunday, December 7th, 2025

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CLA Blue Back Mitten Run

West Hartford, CT

Sunday, December 7th, 2025

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Fleet Feet Poughkeepsie's 2025 Ugly Sweater Run

Poughkeepsie, NY

Sunday, December 7th, 2025

View details for race Fleet Feet Poughkeepsie's 2025 Ugly Sweater Run

Christopher Martin's Christmas Run for Children

New Haven, CT

Sunday, December 7th, 2025

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Santa Shuffle 5k

Longmeadow, MA

Saturday, December 13th, 2025

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BPT PAL Christmas Village Road Race

Trumbull, CT

Saturday, December 13th, 2025

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8th Annual Taco Trials

Rocky Hill, CT

Sunday, December 14th, 2025

10 Miles

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Reindeer Dash

Chaplin, CT

Sunday, December 14th, 2025

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Fleet Feet Poughkeepsie's Red Suit Ramble

Wappingers Falls, NY

Wednesday, December 17th, 2025

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The Scrooge Scramble 5K

Vernon Rockville, CT

Thursday, December 25th, 2025

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Frosty 5K

Guilford, CT

Thursday, January 1st, 2026

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Chilly Chili Run

Orange, CT

Thursday, January 1st, 2026

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Gordy's First Race to benefit the Boys & Girls ...

Westfield, MA

Thursday, January 1st, 2026

10K

View details for race Gordy's First Race to benefit the Boys & Girls Club of Greater Westfield

Brookfield Lions Run for Sight 4-Miler

Brookfield, CT

Thursday, January 1st, 2026

Fast

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Explore more in Winsted, CT

Distances:

5K 10K Half Marathon Marathon

Months:

November December January

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Connecticut races

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