Upcoming 5K Races Near Osterville, MA

Name: The Wine Run at Sakonnet Vineyard
Start: 2026-10-17
End: 2026-10-17
Location: Little Compton

Southcoast Community Wellness 5K

New Bedford, MA

Saturday, May 16th, 2026

Featured

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Runnin' for a Cause, Not from the Cops

Nantucket, MA

Saturday, May 16th, 2026

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

Jordan's Furniture Walk/Run For Adoption

East Taunton, MA

Sunday, May 17th, 2026

View details for race Jordan's Furniture Walk/Run For Adoption

Evan's Run

Norwell, MA

Sunday, May 17th, 2026

View details for race Evan's Run

$16th YPD Blue 5K Run \ Walk For A Reason logo$

16th YPD Blue 5K Run \ Walk For A Reason

South Yarmouth, MA

Sunday, May 17th, 2026

1 Mile

View details for race 16th YPD Blue 5K Run \ Walk For A Reason

32nd Annual Martha's Vineyard Memorial Road Race

Oak Bluffs, MA

Sunday, May 24th, 2026

1 Mile

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

Run Your Axe Off 5k

Tiverton, RI

Saturday, May 30th, 2026

View details for race Run Your Axe Off 5k

CRR Inflatable Costume Fun Run

Plymouth, MA

Saturday, May 30th, 2026

View details for race CRR Inflatable Costume Fun Run

3rd Annual RHS XC/T&F Bulldog Dash 5k

Rockland, MA

Saturday, June 6th, 2026

View details for race 3rd Annual RHS XC/T&F Bulldog Dash 5k

The Wine Run at Westport Rivers Vineyard & Winery

Westport, MA

Sunday, June 7th, 2026

Trail

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Black Hat Brew 5k

Bridgewater, MA

Sunday, June 7th, 2026

1 Mile

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Beach & Back Half Marathon & 5K

Marshfield, MA

Sunday, June 14th, 2026

Half

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El Dredge Fun(d) Run

Hyannis, MA

Sunday, June 14th, 2026

View details for race El Dredge Fun(d) Run

Narragansett Summer Nights 5k

Bristol, RI

Thursday, June 18th, 2026

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Healthy Hustle 5K

Harwich, MA

Saturday, June 20th, 2026

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South Shore Food Bank FRESH BITE 5K

Hingham, MA

Saturday, June 20th, 2026

1 Mile

View details for race South Shore Food Bank FRESH BITE 5K

25th Annual Race for Open Space

Nantucket, MA

Saturday, June 27th, 2026

10K

View details for race 25th Annual Race for Open Space

Chris Demling 5k

North Easton, MA

Saturday, June 27th, 2026

View details for race Chris Demling 5k

Run Into Summer/Blueberry Pie 5K, 1 Mile, Pie E...

Osterville, MA

Saturday, June 27th, 2026

1 Mile

View details for race Run Into Summer/Blueberry Pie 5K, 1 Mile, Pie Eating Contest

Miles of Kindness — 5K, 10K, 1 Mile Family Walk

Fall River, MA

Sunday, June 28th, 2026

10K

1 Mile

View details for race Miles of Kindness — 5K, 10K, 1 Mile Family Walk

Berkley Common Classic 5K

Berkley, MA

Sunday, June 28th, 2026

View details for race Berkley Common Classic 5K

Firecracker Classic Road Race

Cotuit, MA

Thursday, July 2nd, 2026

Fast

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Billington Memorial 5K

Somerset, MA

Saturday, July 4th, 2026

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Nantucket Firecracker 5k Run & Walk

Nantucket, MA

Saturday, July 4th, 2026

View details for race Nantucket Firecracker 5k Run & Walk

Poppy Road Race 2025

Popponesset, MA

Saturday, July 11th, 2026

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Greenvale Vineyards Wine Run 5k

Portsmouth, RI

Sunday, July 19th, 2026

View details for race Greenvale Vineyards Wine Run 5k

2026 Flutie 5K for Autism: Martha's Vineyard

West Tisbury, MA

Saturday, July 25th, 2026

View details for race 2026 Flutie 5K for Autism: Martha's Vineyard

Chilmark Road Race 5K

Chilmark, MA

Saturday, August 8th, 2026

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Vineyard Classic 5k

Oak Bluffs, MA

Tuesday, August 11th, 2026

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5K and Fun Run for Jabberwocky

Edgartown, MA

Saturday, August 15th, 2026

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Bulldog Dash 5k

Marion, MA

Saturday, September 5th, 2026

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FOOT IT FOR FELIX 5K

Edgartown, MA

Saturday, September 5th, 2026

Trail

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Marshfield Run for the Hills

Marshfield Hills, MA

Monday, September 7th, 2026

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Zachary M. Martin Memorial Run/Walk 2026 Rhode ...

Bristol, RI

Saturday, September 12th, 2026

View details for race Zachary M. Martin Memorial Run/Walk 2026 Rhode Island

Bishstrong Foundation 5K Run, Walk & Roll

Westport, MA

Sunday, September 13th, 2026

View details for race Bishstrong Foundation 5K Run, Walk & Roll

Eastham Windmill Weekend Road Race

Eastham, MA

Sunday, September 13th, 2026

View details for race Eastham Windmill Weekend Road Race

Shirley May France 10k Road Race

Somerset, MA

Saturday, September 19th, 2026

10K

1 Mile

View details for race Shirley May France 10k Road Race

24th ANNUAL NAACP GEORGE V. TANKARD, JR. MEMOR...

Oak Bluffs, MA

Saturday, September 19th, 2026

1 Mile

View details for race 24th ANNUAL NAACP GEORGE V. TANKARD, JR. MEMORIAL 5K Run/Walk AND 1 MILE FUN RUN

The East Bay Running Festival

Warren, RI

Saturday, September 19th, 2026

10K

1 Mile

Fast

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NAFI Run 4 The Kidz

Bristol, RI

Sunday, September 20th, 2026

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5K For the Children

Harwich Port, MA

Saturday, September 26th, 2026

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5K For the Children

West Harwich, MA

Saturday, September 26th, 2026

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Race for Recovery 2026

Nantucket, MA

Sunday, September 27th, 2026

1 Mile

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Barrington 5K Run Festival

Barrington, RI

Saturday, October 3rd, 2026

1 Mile

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Paul Funk's Dolphin Dash

South Yarmouth, MA

Saturday, October 3rd, 2026

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Southcoast Health Cancer Care Nicole Podkowa 5k

Fairhaven, MA

Sunday, October 4th, 2026

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Feet for Flippers 5K

Bourne, MA

Saturday, October 10th, 2026

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BMS Athletic Booster Club 5K

North Dighton, MA

Sunday, October 11th, 2026

1 Mile

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SSCPS Annual Road Race 5K

Hingham, MA

Saturday, October 17th, 2026

View details for race SSCPS Annual Road Race 5K

The Wine Run at Sakonnet Vineyard

Little Compton, RI

Saturday, October 17th, 2026

Trail

View details for race The Wine Run at Sakonnet Vineyard

Explore more in Osterville, 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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