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

F.I.T. 'Rock Trail Race

Cumberland, RI

Saturday, March 14th, 2026

Featured

5K

Ultra

1 Mile

Trail

View details for race F.I.T. 'Rock Trail Race

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Ramsey's Run

Kingston, MA

Saturday, March 14th, 2026

5K

Trail

View details for race Ramsey's Run

Tortoise and the Hare Trail Races

Salisbury, MA

Saturday, April 4th, 2026

10K

5K

1 Mile

Trail

View details for race Tortoise and the Hare Trail Races

The Next Loop Endurance Series - New England

Wrentham, MA

Saturday, April 11th, 2026

Trail

View details for race The Next Loop Endurance Series - New England

Radish Rambler 5k @ White Barn Farm

Wrentham, MA

Saturday, April 25th, 2026

5K

Trail

View details for race Radish Rambler 5k @ White Barn Farm

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

Newburyport, MA

Saturday, May 2nd, 2026

5K

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

Watuppa Trail Races

Fall River, MA

Saturday, May 9th, 2026

10K

Ultra

Trail

Fast

View details for race Watuppa Trail Races

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

5K

1 Mile

Trail

View details for race Powisset Farm Trail Run - Spring

Wildcat 5K Trail Run-Walk-Wag

Boxford, MA

Saturday, May 30th, 2026

5K

Trail

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

Brookline Bolt 5K Run/Walk by Scribbles

Brookline, NH

Sunday, May 31st, 2026

5K

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

5K

Trail

View details for race Marblehead Festival of Arts Road Races

The Wine Run at Westport Rivers Vineyard & Winery

Westport, MA

Sunday, June 7th, 2026

5K

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

5K

Trail

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

Stone Tower Half Marthon

Lynn, MA

Sunday, June 21st, 2026

Half

Trail

View details for race Stone Tower Half Marthon

Watermelon Wobbler 5k @ White Barn Farm

Wrentham, MA

Saturday, August 15th, 2026

5K

Trail

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

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

Warwick, RI

Saturday, September 26th, 2026

5K

Trail

Fast

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

Pumpkin Pacer 5k @ White Barn Farm

Wrentham, MA

Saturday, October 24th, 2026

5K

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

5K

Trail

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

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

Salisbury, MA

Thursday, November 26th, 2026

5K

Trail

Fast

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:

January February March

Tags:

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State:

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