Upcoming 5K Races Near Cheshire, CT

Name: 17th Annual Saybrook Point 5k Road Race 2026
Start: 2026-08-22
End: 2026-08-22
Location: Old Saybrook

2025 Norwalk Jingle Bell 5K

Norwalk, CT

Saturday, December 13th, 2025

Featured

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Santa Shuffle 5k

Longmeadow, MA

Saturday, December 13th, 2025

View details for race Santa Shuffle 5k

BPT PAL Christmas Village Road Race

Trumbull, CT

Saturday, December 13th, 2025

View details for race BPT PAL Christmas Village Road Race

Niantic Jingle 5k

Niantic, CT

Saturday, December 13th, 2025

View details for race Niantic Jingle 5k

Reindeer Dash

Chaplin, CT

Sunday, December 14th, 2025

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The Holiday Run & Walk For Toys

Stratford, CT

Sunday, December 14th, 2025

View details for race The Holiday Run & Walk For Toys

2025 Jingle Bell Run - Madison, CT

Madison, CT

Sunday, December 14th, 2025

View details for race 2025 Jingle Bell Run - Madison, CT

New Canaan Santa Run 2025

New Canaan, CT

Saturday, December 20th, 2025

1 Mile

View details for race New Canaan Santa Run 2025

Battle for Burnett

Fairfield, CT

Sunday, December 21st, 2025

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The Scrooge Scramble 5K

Vernon Rockville, CT

Thursday, December 25th, 2025

View details for race The Scrooge Scramble 5K

Frosty 5K

Guilford, 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

Chilly Chili Run

Orange, CT

Thursday, January 1st, 2026

View details for race Chilly Chili Run

Fleet Feet Hartford Winter 2026 Training Programs

West Hartford, CT

Saturday, January 3rd, 2026

10K

View details for race Fleet Feet Hartford Winter 2026 Training Programs

MADD Dry 5K

Fairfield, CT

Sunday, January 4th, 2026

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Brian Aselton East Hartford 5K Snow Dash

East Hartford, CT

Sunday, January 4th, 2026

View details for race Brian Aselton East Hartford 5K Snow Dash

IRIS Run for Refugees

New Haven, CT

Sunday, February 8th, 2026

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99.1PLR CrossPoint Federal Credit Union ShamRoc...

New Haven, CT

Sunday, March 1st, 2026

View details for race 99.1PLR CrossPoint Federal Credit Union ShamRock & Roll 5K

EDRRC - St. Patrick's 5K Run/Walk

Dover Plains, NY

Saturday, March 14th, 2026

View details for race EDRRC - St. Patrick's 5K Run/Walk

Run To End Homelessness 5K10K Walk/Run

Springfield, MA

Saturday, March 14th, 2026

10K

View details for race Run To End Homelessness 5K10K Walk/Run

Ospreys Dominion Wine Run 5k

Peconic, NY

Saturday, March 21st, 2026

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Annual Johnny's Jog for Charity 5K - Blue Back ...

West Hartford, CT

Sunday, March 22nd, 2026

View details for race Annual Johnny's Jog for Charity 5K - Blue Back Square, West Hartford

Beach Bunny 5K

Fairfield, CT

Saturday, March 28th, 2026

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Big Heart 5k

Center Moriches, NY

Saturday, March 28th, 2026

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Bradley Road Race - 5K & 10K

Windsor Locks, CT

Saturday, March 28th, 2026

10K

View details for race Bradley Road Race - 5K & 10K

NVCC Food Pantry Run/Walk

Waterbury, CT

Sunday, March 29th, 2026

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Hoppin Hodges Rails to Trails 5K

Andover, CT

Sunday, April 5th, 2026

Trail

View details for race Hoppin Hodges Rails to Trails 5K

Ion Bank Cheshire Road Races

Cheshire, CT

Sunday, April 12th, 2026

Half

Trail

Fast

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John Jay Community Trail Race

Cross River, NY

Sunday, April 12th, 2026

Trail

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Farm & Forest All- Terrain 5K & Hog Wild Kids F...

Stamford, CT

Sunday, April 12th, 2026

View details for race Farm & Forest All- Terrain 5K & Hog Wild Kids Fun Run

Race for YOUR Mental Health

Meriden, CT

Saturday, April 18th, 2026

View details for race Race for YOUR Mental Health

Gilbert Joseph & Brian Annual 5K (Gilbert JBA5K)

Winsted, CT

Saturday, April 25th, 2026

View details for race Gilbert Joseph & Brian Annual 5K (Gilbert JBA5K)

Deacon Chuck Dietsch Memorial 5K Run & Walk for...

Southbury, CT

Saturday, April 25th, 2026

View details for race Deacon Chuck Dietsch Memorial 5K Run & Walk for Haiti

Brew Run

New London, CT

Saturday, May 2nd, 2026

1 Mile

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2026 Granby Road Race

Granby, CT

Saturday, May 2nd, 2026

10K

1 Mile

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Mount Archer Trail Race

Lyme, CT

Sunday, May 3rd, 2026

Trail

Fast

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WeCare-Mother's Day 5K

Brookfield, CT

Sunday, May 10th, 2026

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Stamford Boys & Girls Club Corporate 5K at Mill...

Stamford, CT

Thursday, May 14th, 2026

View details for race Stamford Boys & Girls Club Corporate 5K at Mill River Park

RESERVOIR RUSH

Moodus, CT

Saturday, May 16th, 2026

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End the Stigma: Mental Health Awareness 5K

New London, CT

Saturday, May 16th, 2026

View details for race End the Stigma: Mental Health Awareness 5K

Outrun Hunger 5K race - and 1-mile fun walk

Springfield, MA

Sunday, May 17th, 2026

1 Mile

View details for race Outrun Hunger 5K race - and 1-mile fun walk

Run the Vineyards - Memorial Day at Pindar 5K

Peconic, NY

Sunday, May 24th, 2026

1 Mile

Trail

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Oh Boy 5K

Waterbury, CT

Monday, May 25th, 2026

Trail

Fast

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EDRRC - Eagle Run 5K Run/Walk and Kids Run

Clinton Corners, NY

Saturday, May 30th, 2026

View details for race EDRRC - Eagle Run 5K Run/Walk and Kids Run

Athletic Brewing Company Fairfield Road Races

Fairfield, CT

Saturday, June 6th, 2026

Half

10K

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SongStrong 5K

Guilford, CT

Saturday, June 6th, 2026

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2026 New England Series - Day 1 (CT)

Simsbury, CT

Monday, June 8th, 2026

10K

Half

View details for race 2026 New England Series - Day 1 (CT)

46th Annual Springfield JCC Father's Day Road Race

Springfield, MA

Sunday, June 21st, 2026

10K

1 Mile

View details for race 46th Annual Springfield JCC Father's Day Road Race

Run the Vineyards - Pindar Vineyards 5K

Peconic, NY

Sunday, July 26th, 2026

Trail

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

17th Annual Saybrook Point 5k Road Race 2026

Old Saybrook, CT

Saturday, August 22nd, 2026

View details for race 17th Annual Saybrook Point 5k Road Race 2026

Explore more in Cheshire, CT

Distances:

5K 10K Half Marathon Marathon

Months:

December January February

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Connecticut races

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