Upcoming Races Near Oak Bluffs, MA - Matching: Trail Races

Name: Li'l Rhody Runaround Trail Run
Start: 2026-11-15
End: 2026-11-15
Location: Charlestown

F.I.T. 'Rock Trail Race

Cumberland, RI

Saturday, March 14th, 2026

Featured

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

Trail

View details for race Ramsey's Run

Hope with Every Stride 5k/10k

Medfield, MA

Saturday, April 11th, 2026

10K

Trail

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

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

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

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

Run for the Pumpkins Trail Run

Westerly, RI

Saturday, October 3rd, 2026

10K

Trail

View details for race Run for the Pumpkins Trail Run

The Wine Run at Sakonnet Vineyard

Little Compton, RI

Saturday, October 17th, 2026

Trail

View details for race The Wine Run at Sakonnet Vineyard

Grills Trail Run

Westerly, RI

Saturday, October 24th, 2026

10 Miles

10K

Trail

View details for race Grills Trail Run

Li'l Rhody Runaround Trail Run

Charlestown, RI

Sunday, November 15th, 2026

Trail

View details for race Li'l Rhody Runaround Trail Run

Explore more in Oak Bluffs, MA

Distances:

5K 10K Half Marathon Marathon

Months:

December January February

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Massachusetts races

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