Upcoming Races Near Bennington, VT in May, 2026

Seven Sisters Trail Race Charity Bibs

Amherst, MA

Saturday, May 2nd, 2026

Featured

Trail

View details for race Seven Sisters Trail Race Charity Bibs

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Orange Fire Department 5K

Orange, MA

Saturday, May 2nd, 2026

5K

View details for race Orange Fire Department 5K

Tulip Trot 5K Run/Walk & Sprout Sprint

Brattleboro, VT

Saturday, May 2nd, 2026

1 Mile

5K

Fast

View details for race Tulip Trot 5K Run/Walk & Sprout Sprint

Bacon Hill Bonanza 5K/10K Road Race, 1-Mile Kid...

Schuylerville, NY

Saturday, May 2nd, 2026

5K

10K

1 Mile

View details for race Bacon Hill Bonanza 5K/10K Road Race, 1-Mile Kids Fun Run AND Virtual 5k/10k/1 Mile Run or Walk

22nd Annual Bulldog 4 Fun Run/Walk

Westmoreland, NH

Saturday, May 2nd, 2026

View details for race 22nd Annual Bulldog 4 Fun Run/Walk

University of Albany - Blue Jean Mile

Albany, NY

Saturday, May 2nd, 2026

1 Mile

View details for race University of Albany - Blue Jean Mile

Sasha's Superhero Run - 8th Annual

Halfmoon, NY

Sunday, May 3rd, 2026

5K

View details for race Sasha's Superhero Run - 8th Annual

Runway 5K

Northampton, MA

Sunday, May 3rd, 2026

5K

View details for race Runway 5K

May Day 5K & Family Fun Day!

Keene, NH

Sunday, May 3rd, 2026

5K

1 Mile

View details for race May Day 5K & Family Fun Day!

Dandelion Dash and Mushroom Mile

Hadley, MA

Sunday, May 3rd, 2026

5K

1 Mile

Trail

View details for race Dandelion Dash and Mushroom Mile

2026 Malta Mile

Malta, NY

Saturday, May 9th, 2026

1 Mile

View details for race 2026 Malta Mile

Indian Ladder Farms Spiked Apple 5k

Altamont, NY

Saturday, May 16th, 2026

5K

View details for race Indian Ladder Farms Spiked Apple 5k

Gathering Waters Annual 5K Run/Walk

Keene, NH

Saturday, May 16th, 2026

5K

1 Mile

View details for race Gathering Waters Annual 5K Run/Walk

District Dash 5K Fun Run & Walk

Langdon, NH

Saturday, May 16th, 2026

5K

Trail

View details for race District Dash 5K Fun Run & Walk

Scotia-Glenville Lions Club 5K

Schenectady, NY

Saturday, May 16th, 2026

5K

View details for race Scotia-Glenville Lions Club 5K

Ledge Rock Hill Wine Run 5k

Lake George, NY

Sunday, May 17th, 2026

5K

View details for race Ledge Rock Hill Wine Run 5k

Keene Runway 5K

Swanzey, NH

Sunday, May 17th, 2026

5K

View details for race Keene Runway 5K

Keene Airport 5K

Swanzey, NH

Sunday, May 17th, 2026

5K

View details for race Keene Airport 5K

Doggie and Me 5K

South Londonderry, VT

Monday, May 25th, 2026

5K

View details for race Doggie and Me 5K

Glens Falls Memorial Day Mile

Glens Falls, NY

Monday, May 25th, 2026

1 Mile

Fast

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Glens Falls Hospital Aloha Family 5k and 1 Mile...

Glens Falls, NY

Saturday, May 30th, 2026

5K

1 Mile

Trail

View details for race Glens Falls Hospital Aloha Family 5k and 1 Mile Fun Walk

Rail Trail to the Footbridge 5k and Kids 1k

Granville, NY

Saturday, May 30th, 2026

5K

Trail

View details for race Rail Trail to the Footbridge 5k and Kids 1k

Explore more in Bennington, VT

Distances:

5K 10K Half Marathon Marathon

Months:

Tags:

Trail Boston Qualifiers Fast Courses

State:

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