Upcoming Races Near Middlebury, CT in October, 2025

Name: The Little Guild 12th Annual Run & Wag 5K
Start: 2025-10-18
End: 2025-10-18
Location: Cornwall

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IronHike Endurance Series - Fall 2025 - Mohawk ...

Cornwall, CT

Thursday, October 2nd, 2025

Ultra

Trail

View details for race IronHike Endurance Series - Fall 2025 - Mohawk Mtn, CT, USA

IronHike Series - Fall '25

Mohawk Mtn Ski Area, Cornwall, CT

Thursday, October 2nd, 2025

Ultra

Trail

View details for race IronHike Series - Fall '25

Stayin' Alive 5k and Fun Run

Armonk, NY

Friday, October 3rd, 2025

View details for race Stayin' Alive 5k and Fun Run

Pounding the Pavement for Pink Races

Seymour, CT

Friday, October 3rd, 2025

1 Mile

View details for race Pounding the Pavement for Pink Races

Chasing Ciara's Light 5k/12k Memorial Trail Race

Monroe, CT

Saturday, October 4th, 2025

12K

Trail

View details for race Chasing Ciara's Light 5k/12k Memorial Trail Race

Salmon River 5.5 Mile Run

Colchester, CT

Saturday, October 4th, 2025

Trail

Fast

View details for race Salmon River 5.5 Mile Run

Iron Hike - Fall Kuwohi Trail Half Marathon Plu...

Cornwall, CT

Saturday, October 4th, 2025

View details for race Iron Hike - Fall Kuwohi Trail Half Marathon Plus - 15 Miles | 7,140' Elevation | 12-Hour | Run, Hike or Walk

Iron Hike - Fall Kuwohi Trail Half Marathon Plu...

Cornwall, CT

Saturday, October 4th, 2025

View details for race Iron Hike - Fall Kuwohi Trail Half Marathon Plus Relay - 15 Miles | 7,140' Elevation | 12-Hour

East Hartford Alumni Foundation 5K

East Hartford, CT

Saturday, October 4th, 2025

View details for race East Hartford Alumni Foundation 5K

4th Annual IOL Purple Light Project 5K

Hartford, CT

Saturday, October 4th, 2025

1 Mile

Fast

View details for race 4th Annual IOL Purple Light Project 5K

Hartford HealthCare MidState Medical Center Run...

Meriden, CT

Saturday, October 4th, 2025

View details for race Hartford HealthCare MidState Medical Center Run The Runway 5K

Running for Water for Africa 5K

Milford, CT

Saturday, October 4th, 2025

1 Mile

Fast

View details for race Running for Water for Africa 5K

New Milford River Run 5K & Kids' Superhero Sprint

New Milford, CT

Saturday, October 4th, 2025

Fast

View details for race New Milford River Run 5K & Kids' Superhero Sprint

*READY SET STRIDE * For our Third Annual OAH Race

Simsbury, CT

Saturday, October 4th, 2025

View details for race *READY SET STRIDE * For our Third Annual OAH Race

*READY SET OAH STRIDE * For our Third Annual OA...

Simsbury, CT

Saturday, October 4th, 2025

View details for race *READY SET OAH STRIDE * For our Third Annual OAH Race

Cider Mill Road Race

Tolland, CT

Saturday, October 4th, 2025

1 Mile

View details for race Cider Mill Road Race

TMS Fall 2025 2 Mile Color Run

Torrington, CT

Saturday, October 4th, 2025

View details for race TMS Fall 2025 2 Mile Color Run

Woodbridge 5k

Woodbridge, CT

Saturday, October 4th, 2025

Fast

View details for race Woodbridge 5k

Fast and Furriest 5K Run and 1-Mile Walk

East Longmeadow, MA

Saturday, October 4th, 2025

1 Mile

Fast

View details for race Fast and Furriest 5K Run and 1-Mile Walk

3rd Annual Motivate 5K Walk/Run

Cornwall On Hudson, NY

Saturday, October 4th, 2025

View details for race 3rd Annual Motivate 5K Walk/Run

RIVERHEAD ATHLETIC CLUB'S RUN THE WAVE 5K

Riverhead, NY

Saturday, October 4th, 2025

View details for race RIVERHEAD ATHLETIC CLUB'S RUN THE WAVE 5K

2025 Rail Trail 10K Race

Hamden, CT

Saturday, October 4th, 2025

10K

Trail

View details for race 2025 Rail Trail 10K Race

Anda! 5k

New Haven, CT

Sunday, October 5th, 2025

View details for race Anda! 5k

Big Sky 5K

Farmington, CT

Sunday, October 5th, 2025

View details for race Big Sky 5K

SOLES for All Souls 5K Race/2K Walk

Stony Brook, NY

Sunday, October 5th, 2025

View details for race SOLES for All Souls 5K Race/2K Walk

Run Stanley

Westfield, MA

Sunday, October 5th, 2025

1 Mile

Trail

View details for race Run Stanley

12th Annual Run Back to School 5K, 1 Mile Race ...

Weatogue, CT

Sunday, October 5th, 2025

1 Mile

View details for race 12th Annual Run Back to School 5K, 1 Mile Race & Fun Run

Fishbein / YMCA Community Road Race

Wallingford, CT

Sunday, October 5th, 2025

1 Mile

View details for race Fishbein / YMCA Community Road Race

Apple Harvest Road Races

Southington, CT

Sunday, October 5th, 2025

1 Mile

Trail

View details for race Apple Harvest Road Races

Run the Vineyards - Pindar Fall 5K and 8K

Peconic, NY

Sunday, October 5th, 2025

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

Norfolk Land Trust Trail Race Series/Haystack M...

Norfolk, CT

Sunday, October 5th, 2025

10K

Half

Trail

View details for race Norfolk Land Trust Trail Race Series/Haystack Mountain Challenge

RACE FOR CATHERINE

Newtown, CT

Friday, October 10th, 2025

View details for race RACE FOR CATHERINE

3rd Annual Pumpkin Run Harwinton - 5K and Fall ...

Harwinton, CT

Saturday, October 11th, 2025

View details for race 3rd Annual Pumpkin Run Harwinton - 5K and Fall Festival

LivFree Boos & Brews 5K

Newtown, CT

Saturday, October 11th, 2025

View details for race LivFree Boos & Brews 5K

Zombie Escape Road Race

Watertown, CT

Saturday, October 11th, 2025

View details for race Zombie Escape Road Race

Gemstone Sparkle Sprint 5k

Wilton, CT

Saturday, October 11th, 2025

Trail

View details for race Gemstone Sparkle Sprint 5k

2024 Harry Chapin Memorial Run/Walk Against Hunger

Croton-on-Hudson, NY

Saturday, October 11th, 2025

10K

1 Mile

View details for race 2024 Harry Chapin Memorial Run/Walk Against Hunger

LISTEN TO LEAD VOICES IN MOTION 5K

Hauppauge, NY

Saturday, October 11th, 2025

View details for race LISTEN TO LEAD VOICES IN MOTION 5K

Hartland Harvest Run

East Hartland, CT

Saturday, October 11th, 2025

View details for race Hartland Harvest Run

GRR Race Series 2025: Greenwich Road Runners Fa...

Greenwich, CT

Saturday, October 11th, 2025

1 Mile

View details for race GRR Race Series 2025: Greenwich Road Runners Fall Classic 5K & 1 Mile Run

Eversource Hartford Marathon, Half Marathon, Re...

Hartford, CT

Saturday, October 11th, 2025

Half

Marathon

View details for race Eversource Hartford Marathon, Half Marathon, Relay & Charity 5K

LivFree Seaside Sea Hag 5k & 1 Mile Health Walk

Bridgeport, CT

Sunday, October 12th, 2025

1 Mile

View details for race LivFree Seaside Sea Hag 5k & 1 Mile Health Walk

Abilis 5k

Old Greenwich, CT

Sunday, October 12th, 2025

View details for race Abilis 5k

2nd Annual Randolph School Ramble 5K Run/Walk

Wappingers Falls, NY

Sunday, October 12th, 2025

Trail

View details for race 2nd Annual Randolph School Ramble 5K Run/Walk

2025 Rhinebeck Fall Foliage Half Marathon & 5K

Rhinebeck, NY

Sunday, October 12th, 2025

Half

View details for race 2025 Rhinebeck Fall Foliage Half Marathon & 5K

Tom Centinaro Memorial "Dam" Race

Wolcott, CT

Saturday, October 18th, 2025

Trail

View details for race Tom Centinaro Memorial "Dam" Race

Ivoryton Pumpkin Chase

Ivoryton, CT

Saturday, October 18th, 2025

Trail

View details for race Ivoryton Pumpkin Chase

Color Run

Northport, NY

Saturday, October 18th, 2025

1 Mile

View details for race Color Run

HHNC Meadows & Trails 5K

Cornwall, NY

Saturday, October 18th, 2025

View details for race HHNC Meadows & Trails 5K

The Little Guild 12th Annual Run & Wag 5K

Cornwall, CT

Saturday, October 18th, 2025

View details for race The Little Guild 12th Annual Run & Wag 5K

Explore more in Middlebury, CT

Distances:

5K 10K Half Marathon Marathon

Months:

September October November

Tags:

Trail Boston Qualifiers Fast Courses

State:

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