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Upcoming Races Near Chester, CT

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Roxbury Fall Classic logo

Roxbury Fall Classic

Roxbury, CT

Saturday, November 14th, 2026

Half
Marathon
Ultra
View details for race Roxbury Fall Classic
Hillacious Half Marathon logo

Hillacious Half Marathon

Litchfield, CT

Saturday, November 14th, 2026

Half
10K
View details for race Hillacious Half Marathon
Li'l Rhody Runaround Trail Run logo

Li'l Rhody Runaround Trail Run

Charlestown, RI

Sunday, November 15th, 2026

Trail
View details for race Li'l Rhody Runaround Trail Run
Waterford High School 14th Annual 5K Turkey Trot logo

Waterford High School 14th Annual 5K Turkey Trot

Waterford, CT

Saturday, November 21st, 2026

5K
View details for race Waterford High School 14th Annual 5K Turkey Trot
Roxbury Road Race Series #35 logo

Roxbury Road Race Series #35

Roxbury, CT

Saturday, November 21st, 2026

Trail
View details for race Roxbury Road Race Series #35
Storybook Half Marathon logo

Storybook Half Marathon

Stratford, CT

Saturday, November 21st, 2026

Half
Trail
View details for race Storybook Half Marathon
Annual Kiwanis Turkey Trot Road Race logo

Annual Kiwanis Turkey Trot Road Race

Wallingford, CT

Sunday, November 22nd, 2026

View details for race Annual Kiwanis Turkey Trot Road Race
The Joyce Allen Great Turkey Escape logo

The Joyce Allen Great Turkey Escape

Redding, CT

Thursday, November 26th, 2026

5K
1 Mile
View details for race The Joyce Allen Great Turkey Escape
2026 Manchester Road Race logo

2026 Manchester Road Race

Manchester, CT

Thursday, November 26th, 2026

View details for race 2026 Manchester Road Race
Roxbury Thanksgiving Day Charity Race logo

Roxbury Thanksgiving Day Charity Race

Roxbury, CT

Thursday, November 26th, 2026

5K
View details for race Roxbury Thanksgiving Day Charity Race
Branford Thanksgiving 5K logo

Branford Thanksgiving 5K

Branford, CT

Thursday, November 26th, 2026

5K
Fast
View details for race Branford Thanksgiving 5K
Newtown Turkey Trot logo

Newtown Turkey Trot

Newtown, CT

Thursday, November 26th, 2026

5K
View details for race Newtown Turkey Trot
Run Turkey Run! Thanksgiving Day 5K logo

Run Turkey Run! Thanksgiving Day 5K

Hamden, CT

Thursday, November 26th, 2026

5K
View details for race Run Turkey Run! Thanksgiving Day 5K
Stratford Turkey Day Trot logo

Stratford Turkey Day Trot

Stratford, CT

Thursday, November 26th, 2026

5K
Fast
View details for race Stratford Turkey Day Trot
Roxbury Road Race Series #36 logo

Roxbury Road Race Series #36

Roxbury, CT

Saturday, November 28th, 2026

View details for race Roxbury Road Race Series #36
Norwich Winterfest 5K logo

Norwich Winterfest 5K

Norwich, CT

Saturday, December 5th, 2026

5K
View details for race Norwich Winterfest 5K
Santa Made Me Do It logo

Santa Made Me Do It

Bethlehem, CT

Saturday, December 5th, 2026

5K
View details for race Santa Made Me Do It
CLA Blue Back Mitten Run logo

CLA Blue Back Mitten Run

West Hartford, CT

Sunday, December 6th, 2026

5K
View details for race CLA Blue Back Mitten Run
Niantic Jingle 5k logo

Niantic Jingle 5k

Niantic, CT

Saturday, December 12th, 2026

5K
View details for race Niantic Jingle 5k
2026 Jingle Bell Run - Connecticut logo

2026 Jingle Bell Run - Connecticut

Madison, CT

Sunday, December 13th, 2026

5K
View details for race 2026 Jingle Bell Run - Connecticut
Frosty Forest 5k logo

Frosty Forest 5k

Stratford, CT

Saturday, December 19th, 2026

5K
Trail
View details for race Frosty Forest 5k
Roxbury Road Race Series Season Pass logo

Roxbury Road Race Series Season Pass

Roxbury, CT

Thursday, December 31st, 2026

View details for race Roxbury Road Race Series Season Pass
Brookfield Lions Run for Sight 4-Miler logo

Brookfield Lions Run for Sight 4-Miler

Brookfield, CT

Friday, January 1st, 2027

Fast
View details for race Brookfield Lions Run for Sight 4-Miler
Kelley's Pace Frostbite logo

Kelley's Pace Frostbite

Mystic, CT

Saturday, January 9th, 2027

View details for race Kelley's Pace Frostbite
HTC Winter Series Barkhamsted 8.5/17 mile logo

HTC Winter Series Barkhamsted 8.5/17 mile

Barkhamsted, CT

Sunday, January 10th, 2027

View details for race HTC Winter Series Barkhamsted 8.5/17 mile
Winter Wonderland 5 Miler logo

Winter Wonderland 5 Miler

Milford, CT

Sunday, January 31st, 2027

View details for race Winter Wonderland 5 Miler
99.1 PLR *Shamrock and Roll 5K* logo

99.1 PLR *Shamrock and Roll 5K*

New Haven, CT

Sunday, March 7th, 2027

5K
View details for race 99.1 PLR *Shamrock and Roll 5K*
Catch A Leprechaun 5K logo

Catch A Leprechaun 5K

Essex, CT

Saturday, March 13th, 2027

5K
View details for race Catch A Leprechaun 5K
Ospreys Dominion Wine Run 5k logo

Ospreys Dominion Wine Run 5k

Peconic, NY

Saturday, March 20th, 2027

5K
View details for race Ospreys Dominion Wine Run 5k
3rd Annual Camp Mountain Laurel - Color Run & Trail Run logo

3rd Annual Camp Mountain Laurel - Color Run & T...

Hamden, CT

Saturday, May 8th, 2027

View details for race 3rd Annual Camp Mountain Laurel - Color Run & Trail Run
2026 Rossiter Run 5K Race and Fun Run/Walk logo

2026 Rossiter Run 5K Race and Fun Run/Walk

Washington Depot, CT

Sunday, May 16th, 2027

5K
View details for race 2026 Rossiter Run 5K Race and Fun Run/Walk
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