56 Upcoming 5K Races Near Chesterfield, MA

Most popular races in Massachusetts →

Sat, Nov 710 races

12th Annual MDS Run~Walk~Smile logo

12th Annual MDS Run~Walk~Smile

Keene, NH

5K
10K
1 Mile
View details for race 12th Annual MDS Run~Walk~Smile
Annual Home Of The Brave 5K Walk or Run - Fundraiser For Sturbridge Vets logo

Annual Home Of The Brave 5K Walk or Run - Fundr...

Sturbridge, MA

5K
View details for race Annual Home Of The Brave 5K Walk or Run - Fundraiser For Sturbridge Vets
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East Windsor Veterans Day 5K Road Race logo

East Windsor Veterans Day 5K Road Race

Broad Brook, CT

5K
View details for race East Windsor Veterans Day 5K Road Race
UCS Superhero 5K and Kids' Dash logo

UCS Superhero 5K and Kids' Dash

Bennington, VT

5K
View details for race UCS Superhero 5K and Kids' Dash

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The 26th Annual Ed McGuire Memorial Cannonball Run logo

The 26th Annual Ed McGuire Memorial Cannonball Run

Falls Village, CT

5K
View details for race The 26th Annual Ed McGuire Memorial Cannonball Run
Run for Ryan 5K and 1 Mile Walk logo

Run for Ryan 5K and 1 Mile Walk

Wilbraham, MA

5K
1 Mile
View details for race Run for Ryan 5K and 1 Mile Walk
Run for the Riverfront 5K logo

Run for the Riverfront 5K

Hartford, CT

5K
View details for race Run for the Riverfront 5K

2026 Harper Grace Memorial 5K Run/Walk

Winchendon, MA

5K
View details for race 2026 Harper Grace Memorial 5K Run/Walk
Orange Turkey Trot logo

Orange Turkey Trot

Orange, MA

5K
View details for race Orange Turkey Trot
Coach Mike Lawrence Twilight Run logo

Coach Mike Lawrence Twilight Run

Gardner, MA

5K
View details for race Coach Mike Lawrence Twilight Run

Sun, Nov 82 races

MPower Youth Running Festival  |  5K  ·  1-Mile  ·  Fun Run logo

MPower Youth Running Festival | 5K · 1-Mile...

Farmington, CT

1 Mile
5K
View details for race MPower Youth Running Festival | 5K · 1-Mile · Fun Run
Monson Memorial Classic Half Marathon & 5K logo

Monson Memorial Classic Half Marathon & 5K

Monson, MA

Half
5K
Fast
View details for race Monson Memorial Classic Half Marathon & 5K

Wed, Nov 111 race

Run 'Round the Mountain OPEN 5K / 10K logo

Run 'Round the Mountain OPEN 5K / 10K

Deerfield, MA

10K
5K
View details for race Run 'Round the Mountain OPEN 5K / 10K

Sat, Nov 142 races

Westfield State Turkey Trot logo

Westfield State Turkey Trot

Westfield, MA

5K
View details for race Westfield State Turkey Trot
2026 Hartford HealthCare Community 5K logo

2026 Hartford HealthCare Community 5K

Hartford, CT

5K
Trail
View details for race 2026 Hartford HealthCare Community 5K

Sun, Nov 152 races

Ox Trot 5K logo

Ox Trot 5K

Sturbridge, MA

5K
View details for race Ox Trot 5K
Glastonbury River Runners Race To Fill the Pantry - Presented by Fleet Feet logo

Glastonbury River Runners Race To Fill the Pant...

Glastonbury, CT

5K
View details for race Glastonbury River Runners Race To Fill the Pantry - Presented by Fleet Feet

Sat, Nov 211 race

Roadtown Turkey Trot 5k logo

Roadtown Turkey Trot 5k

Shutesbury, MA

5K
View details for race Roadtown Turkey Trot 5k

Thu, Nov 2610 races

2026 Web Hill Turkey Trot - 5K logo

2026 Web Hill Turkey Trot - 5K

West Hartford, CT

5K
View details for race 2026 Web Hill Turkey Trot - 5K
Turkey Trot logo

Turkey Trot

Adams, MA

5K
View details for race Turkey Trot
YMCA Athol Turkey Trot 5K & Kid's Fun Run logo

YMCA Athol Turkey Trot 5K & Kid's Fun Run

Athol, MA

5K
Fast
View details for race YMCA Athol Turkey Trot 5K & Kid's Fun Run
Give 'Em the Bird 5k Run / 2K Walk (12th Annual) logo

Give 'Em the Bird 5k Run / 2K Walk (12th Annual)

Easthampton, MA

5K
Trail
View details for race Give 'Em the Bird 5k Run / 2K Walk (12th Annual)
15th Annual Stuffing the Pantry 5k Run/Walk logo

15th Annual Stuffing the Pantry 5k Run/Walk

East Longmeadow, MA

5K
View details for race 15th Annual Stuffing the Pantry 5k Run/Walk
Running of the Turkeys logo

Running of the Turkeys

Arlington, VT

5K
1 Mile
View details for race Running of the Turkeys
Brattleboro Turkey Trot logo

Brattleboro Turkey Trot

Brattleboro, VT

1 Mile
5K
View details for race Brattleboro Turkey Trot

GIVE THANKS. GIVE BACK. GIVE HOPE. 

Templeton, MA

View details for race GIVE THANKS. GIVE BACK. GIVE HOPE. 
15th Annual O'BRiley 5K Turkey Trot AT 9AM logo

15th Annual O'BRiley 5K Turkey Trot AT 9AM

Collinsville, CT

5K
View details for race 15th Annual O'BRiley 5K Turkey Trot AT 9AM
Falcon 5K Turkey Trot logo

Falcon 5K Turkey Trot

Avon, CT

5K
View details for race Falcon 5K Turkey Trot

Fri, Nov 271 race

Run Like Kat logo

Run Like Kat

Longmeadow, MA

5K
1 Mile
View details for race Run Like Kat

Sat, Nov 281 race

Wolf Swamp Turkey Trot 5K Run/Walk logo

Wolf Swamp Turkey Trot 5K Run/Walk

Longmeadow, MA

5K
View details for race Wolf Swamp Turkey Trot 5K Run/Walk

Sun, Nov 293 races

2026 Trot With Ted 5K, 10K and Kids Fun Run logo

2026 Trot With Ted 5K, 10K and Kids Fun Run

Fiskdale, MA

5K
10K
View details for race 2026 Trot With Ted 5K, 10K and Kids Fun Run
Gorge après Gorge logo

Gorge après Gorge

Chesterfield, MA

5K
Trail
View details for race Gorge après Gorge
Miles for Healing logo

Miles for Healing

Orange, MA

5K
View details for race Miles for Healing

Sat, Dec 52 races

Frosty Falcon 5K

Bristol, CT

5K
1 Mile
Fast
View details for race Frosty Falcon 5K

Scores Ugly Sweater Run

Keene, NH

5K
View details for race Scores Ugly Sweater Run

Sun, Dec 61 race

CLA Blue Back Mitten Run logo

CLA Blue Back Mitten Run

West Hartford, CT

5K
View details for race CLA Blue Back Mitten Run

Sat, Dec 121 race

Santa Shuffle 5k logo

Santa Shuffle 5k

Longmeadow, MA

5K
View details for race Santa Shuffle 5k

Sun, Dec 131 race

Every Step Fills a Plate logo

Every Step Fills a Plate

Athol, MA

5K
View details for race Every Step Fills a Plate

Fri, Dec 251 race

The Scrooge Scramble  5K - Rails to Trails - Vernon logo

The Scrooge Scramble 5K - Rails to Trails - Ve...

Vernon Rockville, CT

5K
Trail
View details for race The Scrooge Scramble 5K - Rails to Trails - Vernon

Fri, Jan 1, 20271 race

Gordy's First Race to benefit the Boys & Girls Club of Greater Westfield logo

Gordy's First Race to benefit the Boys & Girls ...

Westfield, MA

5K
10K
View details for race Gordy's First Race to benefit the Boys & Girls Club of Greater Westfield

Sun, Jan 10, 20271 race

Brian Aselton East Hartford 5K Snow Dash logo

Brian Aselton East Hartford 5K Snow Dash

East Hartford, CT

5K
View details for race Brian Aselton East Hartford 5K Snow Dash

Sat, Feb 13, 20271 race

Heart & Soles 5K logo

Heart & Soles 5K

Keene, NH

5K
View details for race Heart & Soles 5K

Sat, Apr 10, 20271 race

Big Cheese 5K logo

Big Cheese 5K

Athol, MA

5K
View details for race Big Cheese 5K

Sun, Apr 25, 20272 races

Dandelion Dash and Mushroom Mile logo

Dandelion Dash and Mushroom Mile

Hadley, MA

5K
1 Mile
Trail
View details for race Dandelion Dash and Mushroom Mile
Veterans in Motion 5K logo

Veterans in Motion 5K

Haydenville, MA

5K
1 Mile
View details for race Veterans in Motion 5K

Sat, May 1, 20271 race

2027 Granby Road Race logo

2027 Granby Road Race

Granby, CT

5K
10K
1 Mile
View details for race 2027 Granby Road Race

Sun, May 2, 20271 race

Runway 5K logo

Runway 5K

Northampton, MA

5K
View details for race Runway 5K

Sun, May 16, 20271 race

Keene Airport 5K logo

Keene Airport 5K

Swanzey, NH

5K
Fast
View details for race Keene Airport 5K

Mon, Jun 7, 20271 race

2027 New England Series - Day 1 (CT) logo

2027 New England Series - Day 1 (CT)

Simsbury, CT

Marathon
Half
5K
View details for race 2027 New England Series - Day 1 (CT)

Wed, Jun 9, 20271 race

2027 New England Series - Day 3 (MA) logo

2027 New England Series - Day 3 (MA)

Holyoke, MA

10K
5K
Half
View details for race 2027 New England Series - Day 3 (MA)
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