Upcoming Races Near Gloucester, MA - Matching: Trail Races

Name: Will Run for Pie - Turkey Trot 5K Run/Walk
Start: 2026-11-26
End: 2026-11-26
Location: Salisbury

Ramsey's Run

Kingston, MA

Saturday, March 14th, 2026

Featured

Trail

View details for race Ramsey's Run

Want to feature your race?

Get your race seen first by thousands of runners

Learn More

Learn how to feature your race

Hope with Every Stride 5k/10k

Medfield, MA

Saturday, April 11th, 2026

10K

Trail

View details for race Hope with Every Stride 5k/10k

Cancer Doesn't Care But WE Do 5K Run/Walk

Newburyport, MA

Saturday, May 2nd, 2026

Trail

View details for race Cancer Doesn't Care But WE Do 5K Run/Walk

The Aviation Museum of New Hampshire's Run the ...

Londonderry, NH

Saturday, May 2nd, 2026

Trail

View details for race The Aviation Museum of New Hampshire's Run the Rail Trail 4-Miler

4K Trail Run

Boston, MA

Wednesday, May 20th, 2026

Trail

View details for race 4K Trail Run

Powisset Farm Trail Run - Spring

Dover, MA

Monday, May 25th, 2026

1 Mile

Trail

View details for race Powisset Farm Trail Run - Spring

Wildcat 5K Trail Run-Walk-Wag

Boxford, MA

Saturday, May 30th, 2026

Trail

View details for race Wildcat 5K Trail Run-Walk-Wag

Operation Mohawk Tactical 2

Foxboro, MA

Saturday, May 30th, 2026

Trail

View details for race Operation Mohawk Tactical 2

Marblehead Festival of Arts Road Races

Marblehead, MA

Monday, June 1st, 2026

1 Mile

10K

Trail

View details for race Marblehead Festival of Arts Road Races

Friends of Holliston Trails 5K & 10K

Holliston, MA

Saturday, June 6th, 2026

10K

Trail

View details for race Friends of Holliston Trails 5K & 10K

Charlestown Boys & Girls Club's Battle of Bunke...

Charlestown, MA

Sunday, June 14th, 2026

Trail

View details for race Charlestown Boys & Girls Club's Battle of Bunker Hill 5K Road Race

Stone Tower Half Marathon

Lynn, MA

Sunday, June 21st, 2026

Half

Trail

View details for race Stone Tower Half Marathon

Mt. A Trail Challenge 5K/1 Mile

York, ME

Saturday, September 19th, 2026

1 Mile

Trail

View details for race Mt. A Trail Challenge 5K/1 Mile

Miles For Meals 5k

Nashua, NH

Saturday, September 19th, 2026

Trail

View details for race Miles For Meals 5k

Powisset Farm Trail Run - Fall

Dover, MA

Sunday, October 25th, 2026

1 Mile

Trail

View details for race Powisset Farm Trail Run - Fall

27th Annual Novemberfest Race for the Nashua Ch...

Nashua, NH

Sunday, November 22nd, 2026

Trail

View details for race 27th Annual Novemberfest Race for the Nashua Children's Home

Will Run for Pie - Turkey Trot 5K Run/Walk

Salisbury, MA

Thursday, November 26th, 2026

Trail

Fast

View details for race Will Run for Pie - Turkey Trot 5K Run/Walk

Explore more in Gloucester, MA

Distances:

5K 10K Half Marathon Marathon

Months:

February March April

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Massachusetts races

Don't see your race? Add it!

Add Your Race (Free)