Upcoming 5K Races Near Pawling, NY

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2026 New England Series - Day 1 (CT)

Simsbury, CT

Monday, June 8th, 2026

Featured

10K

Half

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

Fleet Feet Hartford Summer 2026 5k & 10k Traini...

West Hartford, CT

Saturday, June 13th, 2026

10K

View details for race Fleet Feet Hartford Summer 2026 5k & 10k Training Programs

Red, White and Blue in Bethany 5K

Bethany, CT

Saturday, June 13th, 2026

View details for race Red, White and Blue in Bethany 5K

Miles for Smiles

Wyckoff, NJ

Saturday, June 13th, 2026

View details for race Miles for Smiles

6th Annual A. W. Stanley Park 5K

New Britain, CT

Saturday, June 13th, 2026

1 Mile

10K

View details for race 6th Annual A. W. Stanley Park 5K

52nd Annual Rooster Run

Newtown, CT

Saturday, June 13th, 2026

10K

Trail

View details for race 52nd Annual Rooster Run

Run For The Rock

Bridgeport, CT

Sunday, June 14th, 2026

View details for race Run For The Rock

Darien 5K-Run / 1-Mile Walk ( in Support of Ukr...

Darien, CT

Sunday, June 14th, 2026

1 Mile

View details for race Darien 5K-Run / 1-Mile Walk ( in Support of Ukraine )

Milford Rotary Run in the Park 5K

Milford, CT

Sunday, June 14th, 2026

View details for race Milford Rotary Run in the Park 5K

Flag Day 5K

Bethel, CT

Sunday, June 14th, 2026

View details for race Flag Day 5K

Devil Dash 5k

Stratford, CT

Sunday, June 14th, 2026

View details for race Devil Dash 5k

Solstice Sprint 5K

West Hartford, CT

Wednesday, June 17th, 2026

Trail

Fast

View details for race Solstice Sprint 5K

2026 Rushford’s Race for Recovery 5K Color Run

Portland, CT

Saturday, June 20th, 2026

View details for race 2026 Rushford’s Race for Recovery 5K Color Run

Rhulen Rock Hill Run and Ramble 5K

Holiday Mountain Ski Area, NY

Saturday, June 20th, 2026

Fast

View details for race Rhulen Rock Hill Run and Ramble 5K

4th Annual Bloomfield Juneteenth 5K

Bloomfield, CT

Saturday, June 20th, 2026

View details for race 4th Annual Bloomfield Juneteenth 5K

2026 Camp Jewell 5K Fun Run/Walk & Kids 1M

Colebrook, CT

Saturday, June 20th, 2026

1 Mile

Trail

View details for race 2026 Camp Jewell 5K Fun Run/Walk & Kids 1M

Chasing Daylight 5K

Poughkeepsie, NY

Saturday, June 20th, 2026

View details for race Chasing Daylight 5K

Heart of Gold 5K

Oakland, NJ

Sunday, June 21st, 2026

Fast

View details for race Heart of Gold 5K

The Club 2nd Annual 5k!

Naugatuck, CT

Saturday, June 27th, 2026

View details for race The Club 2nd Annual 5k!

EDRRC - Pawling Moonlight Trail Run 5K

Pawling, NY

Saturday, June 27th, 2026

Trail

View details for race EDRRC - Pawling Moonlight Trail Run 5K

Westport Road Runners Summer Series

Westport, CT

Saturday, June 27th, 2026

1 Mile

15K

View details for race Westport Road Runners Summer Series

Tunnel to Towers 5K Run & Walk - Bethel, CT

Bethel, CT

Sunday, June 28th, 2026

Fast

View details for race Tunnel to Towers 5K Run & Walk - Bethel, CT

Fleet Feet Poughkeepsie's 2026 Pride Fun Run to...

Poughkeepsie, NY

Sunday, June 28th, 2026

View details for race Fleet Feet Poughkeepsie's 2026 Pride Fun Run to Benefit Dutchess Pride Center

11th Annual Milford Moves for Veterans 5K

Milford, CT

Sunday, June 28th, 2026

View details for race 11th Annual Milford Moves for Veterans 5K

Fork In The Trail 5k Presented By Peace, Love, ...

Bedford, NY

Sunday, June 28th, 2026

Trail

View details for race Fork In The Trail 5k Presented By Peace, Love, Trails

Fleet Feet Poughkeepsie's 2026 Red, White & Bre...

Newburgh, NY

Friday, July 3rd, 2026

View details for race Fleet Feet Poughkeepsie's 2026 Red, White & Brew 5K Sponsored by ASICS

Milford Road Runners Independence Day 5K

Milford, CT

Saturday, July 4th, 2026

View details for race Milford Road Runners Independence Day 5K

Saugerties Independence Day 5K

Saugerties , NY

Saturday, July 4th, 2026

View details for race Saugerties Independence Day 5K

Glen Rock Tribute Run 5K - July 4th, 2026

Glen Rock, NJ

Saturday, July 4th, 2026

View details for race Glen Rock Tribute Run 5K - July 4th, 2026

2026 Great American Weekend 5k/10k Goshen Rotar...

Goshen, NY

Saturday, July 4th, 2026

10K

View details for race 2026 Great American Weekend 5k/10k Goshen Rotary Run

East Shore 5k

New Haven, CT

Sunday, July 5th, 2026

View details for race East Shore 5k

Roxbury Road Race Series #18

Roxbury, CT

Saturday, July 11th, 2026

View details for race Roxbury Road Race Series #18

Petit Family Foundation 5K

Plainville, CT

Sunday, July 12th, 2026

View details for race Petit Family Foundation 5K

The 39th Annual Women's Distance Festival 5K

Congers, NY

Sunday, July 12th, 2026

View details for race The 39th Annual Women's Distance Festival 5K

PATTERSONS PELLET—53rd Summer Series Week Two

Kerhonkson, NY

Monday, July 13th, 2026

1 Mile

Trail

View details for race PATTERSONS PELLET—53rd Summer Series Week Two

THE FAIRFIELD POLICE SUNSET 5K - Presented by M...

Fairfield, CT

Wednesday, July 15th, 2026

View details for race THE FAIRFIELD POLICE SUNSET 5K - Presented by Moneco Advisors

Ambulance Driver 5K ...

Derby, CT

Wednesday, July 15th, 2026

View details for race Ambulance Driver 5K at BADSONS Brewery

Annual 5K Gardiner Classic Run/Walk

Gardiner, NY

Thursday, July 16th, 2026

Trail

View details for race Annual 5K Gardiner Classic Run/Walk

Bubble Run | Hartford 2026

Hartford, CT

Saturday, July 18th, 2026

View details for race Bubble Run | Hartford 2026

Southwest Cafe Margarita 5K

Ridgefield, CT

Saturday, July 25th, 2026

View details for race Southwest Cafe Margarita 5K

New Milford Parks & Recreation Road Race

New Milford, CT

Saturday, July 25th, 2026

View details for race New Milford Parks & Recreation Road Race

Valley of Hartford 5K Road Race

Newington, CT

Saturday, July 25th, 2026

View details for race Valley of Hartford 5K Road Race

Woodmont 5K

Milford, CT

Saturday, July 25th, 2026

View details for race Woodmont 5K

Surfin' Santa's Christmas In July 5k & Holiday ...

Stratford, CT

Sunday, July 26th, 2026

1 Mile

View details for race Surfin' Santa's Christmas In July 5k & Holiday Stroll

The Trumbull Rotary Sunset 5k Run & Walk

Trumbull, CT

Friday, July 31st, 2026

1 Mile

View details for race The Trumbull Rotary Sunset 5k Run & Walk

It's All Downhill From Here 5K

Wilton, CT

Saturday, August 1st, 2026

Trail

View details for race It's All Downhill From Here 5K

Boys & Girls Club of Milford Ice Cream Run (5K)

Milford, CT

Sunday, August 2nd, 2026

View details for race Boys & Girls Club of Milford Ice Cream Run (5K)

Follow Natural Fitness Women's Health 5K

Bridgeport, CT

Saturday, August 8th, 2026

1 Mile

View details for race Follow Natural Fitness Women's Health 5K

The Perogie Dash

Danbury, CT

Saturday, August 8th, 2026

View details for race The Perogie Dash

Run for Wishes 5K Benefitting MAKE-A-WISH® CONN...

Stratford, CT

Sunday, August 9th, 2026

View details for race Run for Wishes 5K Benefitting MAKE-A-WISH® CONNECTICUT

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