Upcoming 5K Races Near Old Saybrook, CT

Name: 2026 CT LEO Memorial Run
Start: 2026-10-25
End: 2026-10-25
Location: Middletown

2025 NIA Jingle Bell Run - 37th Annual

Trumbull, CT

Saturday, December 6th, 2025

Featured

1 Mile

View details for race 2025 NIA Jingle Bell Run - 37th Annual

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JINGLE BELL JOG 5K AND RUDOLPH'S FUN RUN

Calverton, NY

Saturday, December 6th, 2025

Trail

View details for race JINGLE BELL JOG 5K AND RUDOLPH'S FUN RUN

Santa Made Me Do It

Bethlehem, CT

Saturday, December 6th, 2025

View details for race Santa Made Me Do It

Norwich Winterfest 5K

Norwich, CT

Saturday, December 6th, 2025

View details for race Norwich Winterfest 5K

Christopher Martin's Christmas Run for Children

New Haven, CT

Sunday, December 7th, 2025

View details for race Christopher Martin's Christmas Run for Children

CLA Blue Back Mitten Run

West Hartford, CT

Sunday, December 7th, 2025

View details for race CLA Blue Back Mitten Run

Niantic Jingle 5k

Niantic, CT

Saturday, December 13th, 2025

View details for race Niantic Jingle 5k

BPT PAL Christmas Village Road Race

Trumbull, CT

Saturday, December 13th, 2025

View details for race BPT PAL Christmas Village Road Race

5th Annual Roseland Park Christmas Run 5K, 5M &...

Woodstock, CT

Saturday, December 13th, 2025

View details for race 5th Annual Roseland Park Christmas Run 5K, 5M & Kids Run

The Holiday Run & Walk For Toys

Stratford, CT

Sunday, December 14th, 2025

View details for race The Holiday Run & Walk For Toys

Reindeer Dash

Chaplin, CT

Sunday, December 14th, 2025

View details for race Reindeer Dash

2025 Jingle Bell Run - Connecticut

Madison, CT

Sunday, December 14th, 2025

View details for race 2025 Jingle Bell Run - Connecticut

The Scrooge Scramble 5K

Vernon Rockville, CT

Thursday, December 25th, 2025

View details for race The Scrooge Scramble 5K

Chilly Chili Run

Orange, CT

Thursday, January 1st, 2026

View details for race Chilly Chili Run

Frosty 5K

Guilford, CT

Thursday, January 1st, 2026

View details for race Frosty 5K

MADD Dry 5K

Fairfield, CT

Sunday, January 4th, 2026

View details for race MADD Dry 5K

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

View details for race IRIS Run for Refugees

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

Ospreys Dominion Wine Run 5k

Peconic, NY

Saturday, March 21st, 2026

View details for race Ospreys Dominion Wine Run 5k

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

Big Heart 5k

Center Moriches, NY

Saturday, March 28th, 2026

View details for race Big Heart 5k

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

View details for race NVCC Food Pantry Run/Walk

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

View details for race Ion Bank Cheshire Road Races

Race for YOUR Mental Health

Meriden, CT

Saturday, April 18th, 2026

View details for race Race for YOUR Mental Health

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

Strides For Scholars

Union, CT

Sunday, April 26th, 2026

View details for race Strides For Scholars

Brew Run

New London, CT

Saturday, May 2nd, 2026

1 Mile

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Mount Archer Trail Race

Lyme, CT

Sunday, May 3rd, 2026

Trail

Fast

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RESERVOIR RUSH

Moodus, CT

Saturday, May 16th, 2026

View details for race RESERVOIR RUSH

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

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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Run the Vineyards - Jonathan Edwards 5K

North Stonington, CT

Sunday, May 31st, 2026

View details for race Run the Vineyards - Jonathan Edwards 5K

Athletic Brewing Company Fairfield Road Races

Fairfield, CT

Saturday, June 6th, 2026

Half

10K

View details for race Athletic Brewing Company Fairfield Road Races

SongStrong 5K

Guilford, CT

Saturday, June 6th, 2026

View details for race SongStrong 5K

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)

Run the Vineyards - Pindar Vineyards 5K

Peconic, NY

Sunday, July 26th, 2026

Trail

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

Race of Hope Southampton

Southampton, NY

Sunday, August 2nd, 2026

View details for race Race of Hope Southampton

Stonington Cross Country 5K

Pawcatuck, CT

Wednesday, August 12th, 2026

View details for race Stonington Cross Country 5K

Battle of Stonington 5K

Stonington, CT

Tuesday, August 18th, 2026

Fast

View details for race Battle of Stonington 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

Faxon Law New Haven Road Race

New Haven, CT

Monday, September 7th, 2026

Half

View details for race Faxon Law New Haven Road Race

Run for The Hills

Niantic, CT

Saturday, September 12th, 2026

Trail

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Murray Lender 5K Bagel Run

Woodbridge, CT

Sunday, September 20th, 2026

View details for race Murray Lender 5K Bagel Run

2025 Pies & Pub TaTa Trot 5k

Middlebury, CT

Saturday, September 26th, 2026

View details for race 2025 Pies & Pub TaTa Trot 5k

Run the Vineyards - Pindar Fall 5K and 8K

Peconic, NY

Sunday, October 4th, 2026

View details for race Run the Vineyards - Pindar Fall 5K and 8K

2026 CT LEO Memorial Run

Middletown, CT

Sunday, October 25th, 2026

View details for race 2026 CT LEO Memorial Run

Explore more in Old Saybrook, CT

Distances:

5K 10K Half Marathon Marathon

Months:

December January February

Tags:

Trail Boston Qualifiers Fast Courses

State:

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