Upcoming Races Near Berkshire County, MA in October, 2025

Name: 28th Annual Monson Memorial Classic Half Marathon & 5K
Start: 2025-10-26
End: 2025-10-26
Location: Monson

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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

*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

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

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

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

OAH STRIDES

Simsbury, CT

Saturday, October 4th, 2025

View details for race OAH STRIDES

TMS Fall 2025 2 Mile Color Run

Torrington, CT

Saturday, October 4th, 2025

View details for race TMS Fall 2025 2 Mile Color Run

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

Maddie's Mark 5k

Schenectady, NY

Sunday, October 5th, 2025

View details for race Maddie's Mark 5k

Run Stanley

Westfield, MA

Sunday, October 5th, 2025

1 Mile

Trail

View details for race Run Stanley

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

Halloween Holyoke Firefighters 5K

Holyoke, MA

Saturday, October 11th, 2025

View details for race Halloween Holyoke Firefighters 5K

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

Mahar Cancer Fund Run/ Walk 5K

Orange, MA

Saturday, October 11th, 2025

View details for race Mahar Cancer Fund Run/ Walk 5K

Hartland Harvest Run

East Hartland, CT

Saturday, October 11th, 2025

View details for race Hartland Harvest Run

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

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

The North Face Race to the Summit

Stratton, VT

Monday, October 13th, 2025

View details for race The North Face Race to the Summit

Cider Run/Walk 5k

Warren, CT

Saturday, October 18th, 2025

View details for race Cider Run/Walk 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

Magic for Maddie

Holyoke, MA

Saturday, October 18th, 2025

View details for race Magic for Maddie

Easterseals 5K Your Way Freedom Stride

Farmington, CT

Sunday, October 19th, 2025

View details for race Easterseals 5K Your Way Freedom Stride

Bristol Mum-A-Thon Road Race 2025

Bristol, CT

Sunday, October 19th, 2025

1 Mile

View details for race Bristol Mum-A-Thon Road Race 2025

The Ludlow Clocktower Classic 5k

Ludlow, MA

Saturday, October 25th, 2025

View details for race The Ludlow Clocktower Classic 5k

Center School's Halloween Hustle 5k Run/Walk

Longmeadow, MA

Saturday, October 25th, 2025

View details for race Center School's Halloween Hustle 5k Run/Walk

Donny's Dash

Simsbury, CT

Saturday, October 25th, 2025

View details for race Donny's Dash

2025 Alplaus Runaround

Alplaus, NY

Saturday, October 25th, 2025

1 Mile

Fast

View details for race 2025 Alplaus Runaround

Collinsville Trick or Trot

Collinsville, CT

Saturday, October 25th, 2025

Trail

View details for race Collinsville Trick or Trot

The Northfield Monster Dash 5K 2025

Northfield, MA

Saturday, October 25th, 2025

Fast

View details for race The Northfield Monster Dash 5K 2025

Run to Remember 5K

Troy, NY

Saturday, October 25th, 2025

View details for race Run to Remember 5K

28th Annual Monson Memorial Classic Half Marath...

Monson, MA

Sunday, October 26th, 2025

Half

Fast

View details for race 28th Annual Monson Memorial Classic Half Marathon & 5K

Explore more in Berkshire County, MA

Distances:

5K 10K Half Marathon Marathon

Months:

September October November

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Massachusetts races

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