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Upcoming Races Near Jamaica Plain, MA - Matching: Trail Races

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

Watuppa Trail Races

Fall River, MA

Saturday, May 9th, 2026

Featured

10K

Ultra

Trail

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15th Annual FBRTC 5K Trail Race and Walk

Franklin, MA

Saturday, May 16th, 2026

Trail

View details for race 15th Annual FBRTC 5K Trail Race and Walk

Exeter Day School 5K Trail Race and Kids Fun Run

Exeter, NH

Sunday, May 17th, 2026

Trail

View details for race Exeter Day School 5K Trail Race and Kids Fun Run

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

Brookline Bolt 5K Run/Walk by Scribbles

Brookline, NH

Sunday, May 31st, 2026

Trail

View details for race Brookline Bolt 5K Run/Walk by Scribbles

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

Mine Falls Summer Trail Series

Nashua, NH

Monday, June 1st, 2026

Trail

View details for race Mine Falls Summer Trail Series

Friends of Holliston Trails 5K & 10K

Holliston, MA

Saturday, June 6th, 2026

10K

Trail

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

The Wine Run at Westport Rivers Vineyard & Winery

Westport, MA

Sunday, June 7th, 2026

Trail

View details for race The Wine Run at Westport Rivers Vineyard & Winery

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

TVFR Woodland Trail Series

Uxbridge, MA

Thursday, June 25th, 2026

Trail

View details for race TVFR Woodland Trail Series

Watermelon Wobbler 5k @ White Barn Farm

Wrentham, MA

Saturday, August 15th, 2026

Trail

View details for race Watermelon Wobbler 5k @ White Barn Farm

Miles For Meals 5k

Nashua, NH

Saturday, September 19th, 2026

Trail

View details for race Miles For Meals 5k

Ocean State XC Invitational - Ocean State 5K Tr...

Warwick, RI

Saturday, September 26th, 2026

Trail

Fast

View details for race Ocean State XC Invitational - Ocean State 5K Trail Run

Race for the Refuge

Sudbury, MA

Sunday, September 27th, 2026

10K

Ultra

Trail

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Miles for Mutts 5k Run/Walk

Marlborough, MA

Saturday, October 3rd, 2026

Trail

View details for race Miles for Mutts 5k Run/Walk

Midstate Massive Ultra Trail

New Ipswich, NH

Saturday, October 10th, 2026

Ultra

Trail

View details for race Midstate Massive Ultra Trail

Pumpkin Pacer 5k @ White Barn Farm

Wrentham, MA

Saturday, October 24th, 2026

Trail

View details for race Pumpkin Pacer 5k @ White Barn Farm

The Baystate Dirty Dog Trail Run-Ruck-Walk 5k

Berkley, MA

Sunday, October 25th, 2026

Trail

View details for race The Baystate Dirty Dog Trail Run-Ruck-Walk 5k

Powisset Farm Trail Run - Fall

Dover, MA

Sunday, October 25th, 2026

1 Mile

Trail

View details for race Powisset Farm Trail Run - Fall

Run for the Hills

Harvard, MA

Sunday, October 25th, 2026

1 Mile

Trail

View details for race Run for the Hills

Pawtuxet River 5k: Run of the Mills

Coventry, RI

Saturday, November 7th, 2026

Trail

View details for race Pawtuxet River 5k: Run of the Mills

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

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

Explore more in Jamaica Plain, MA

Distances:

5K 10K Half Marathon Marathon

Months:

May June July

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Massachusetts races

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