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Upcoming Races Near Osterville, MA in May, 2026

Dennis Chamber of Commerce May 5k Road Race/Walk

Dennis, MA

Saturday, May 2nd, 2026

Featured

5K

View details for race Dennis Chamber of Commerce May 5k Road Race/Walk

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Cape Cod Trail Race

Falmouth, MA

Sunday, May 3rd, 2026

Ultra

10K

Trail

View details for race Cape Cod Trail Race

Run Through the Pines Half Marathon & 5K

Carver, MA

Sunday, May 3rd, 2026

Half

5K

View details for race Run Through the Pines Half Marathon & 5K

Nantucket Vineyard Wine Run 5k

Nantucket, MA

Sunday, May 3rd, 2026

5K

View details for race Nantucket Vineyard Wine Run 5k

WHRHS Alumni 5K

Whitman, MA

Sunday, May 3rd, 2026

5K

View details for race WHRHS Alumni 5K

Watuppa Trail Races

Fall River, MA

Saturday, May 9th, 2026

10K

Ultra

Trail

Fast

View details for race Watuppa Trail Races

Mother's Day 5K at the Stoico Firstfed YMCA

Swansea, MA

Saturday, May 9th, 2026

5K

View details for race Mother's Day 5K at the Stoico Firstfed YMCA

Charlie Holder, Sr. Memorial Charity 10K & 5K

Middletown, RI

Saturday, May 9th, 2026

10K

View details for race Charlie Holder, Sr. Memorial Charity 10K & 5K

Charlie Holder Sr. Memorial 5K

Middletown, RI

Saturday, May 9th, 2026

5K

View details for race Charlie Holder Sr. Memorial 5K

Women Run Cape Cod 5k

Falmouth, MA

Sunday, May 10th, 2026

5K

View details for race Women Run Cape Cod 5k

16th Annual Mother's Day 5K Walk & Run

New Bedford, MA

Sunday, May 10th, 2026

5K

View details for race 16th Annual Mother's Day 5K Walk & Run

Mattapoisett Mother’s Day 5K

Mattapoisett, MA

Sunday, May 10th, 2026

5K

View details for race Mattapoisett Mother’s Day 5K

Southcoast Community Wellness 5K

New Bedford, MA

Saturday, May 16th, 2026

5K

View details for race Southcoast Community Wellness 5K

Runnin' for a Cause, Not from the Cops

Nantucket, MA

Saturday, May 16th, 2026

5K

View details for race Runnin' for a Cause, Not from the Cops

Horseneck Half & 3.5 Miler

Westport, MA

Sunday, May 17th, 2026

Half

View details for race Horseneck Half & 3.5 Miler

$19th YPD Blue 5K Run \ Walk For A Reason logo$

19th YPD Blue 5K Run \ Walk For A Reason

South Yarmouth, MA

Sunday, May 17th, 2026

5K

1 Mile

View details for race 19th YPD Blue 5K Run \ Walk For A Reason

Evan's Run

Norwell, MA

Sunday, May 17th, 2026

5K

View details for race Evan's Run

Surf Drive Mile

Falmouth, MA

Sunday, May 17th, 2026

1 Mile

Fast

View details for race Surf Drive Mile

Boots on the Ground for Heroes 5K

Newport, RI

Saturday, May 23rd, 2026

View details for race Boots on the Ground for Heroes 5K

32nd Annual Martha's Vineyard Memorial 5K Road ...

Oak Bluffs, MA

Sunday, May 24th, 2026

5K

1 Mile

View details for race 32nd Annual Martha's Vineyard Memorial 5K Road Race

Run Your Axe Off 5k

Tiverton, RI

Saturday, May 30th, 2026

5K

View details for race Run Your Axe Off 5k

Explore more in Osterville, MA

Distances:

5K 10K Half Marathon Marathon

Months:

March April May

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Massachusetts races

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