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Upcoming Races Near Old Saybrook, CT - Matching: Trail Races

SRC & Friends Supported Long Run

Wading River, NY

Sunday, March 15th, 2026

Featured

15K

Ultra

Trail

View details for race SRC & Friends Supported Long Run

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Enchanted Forest Ultra Run

Stratford, CT

Saturday, March 21st, 2026

Trail

View details for race Enchanted Forest Ultra Run

Hoppin Hodges Rails to Trails 5K

Andover, CT

Sunday, April 5th, 2026

5K

Trail

View details for race Hoppin Hodges Rails to Trails 5K

Ion Bank Cheshire Road Races

Cheshire, CT

Sunday, April 12th, 2026

Half

5K

Trail

Fast

View details for race Ion Bank Cheshire Road Races

Tommy Sullivan's 5K

Branford, CT

Sunday, April 19th, 2026

5K

Trail

View details for race Tommy Sullivan's 5K

Brookhaven Trail 15K and 4 Mile Trail Run

Wading River, NY

Sunday, April 19th, 2026

15K

Trail

View details for race Brookhaven Trail 15K and 4 Mile Trail Run

2026 Deer Lake 5 Mile Trail Run

Killingworth, CT

Sunday, April 26th, 2026

Trail

View details for race 2026 Deer Lake 5 Mile Trail Run

Mount Archer Trail Race

Lyme, CT

Sunday, May 3rd, 2026

5K

Trail

Fast

View details for race Mount Archer Trail Race

Forgotten Forest 9 Hour Ultra

Stratford, CT

Saturday, May 16th, 2026

Trail

View details for race Forgotten Forest 9 Hour Ultra

Run the Vineyards - Memorial Day at Pindar 5K

Peconic, NY

Sunday, May 24th, 2026

5K

1 Mile

Trail

View details for race Run the Vineyards - Memorial Day at Pindar 5K

Oh Boy 5K

Waterbury, CT

Monday, May 25th, 2026

5K

Trail

View details for race Oh Boy 5K

Run in the Park 5K - to benefit the Milford Rot...

Milford, CT

Sunday, June 7th, 2026

5K

Trail

View details for race Run in the Park 5K - to benefit the Milford Rotary and the Beth-El Center

Centurion Trail 33 Hour Ultra

Stratford, CT

Saturday, June 27th, 2026

Trail

View details for race Centurion Trail 33 Hour Ultra

Run the Vineyards - Pindar Vineyards 5K

Peconic, NY

Sunday, July 26th, 2026

5K

Trail

View details for race Run the Vineyards - Pindar Vineyards 5K

Run for The Hills

Niantic, CT

Saturday, September 12th, 2026

5K

Trail

View details for race Run for The Hills

Run for the Pumpkins Trail Run

Westerly, RI

Saturday, October 3rd, 2026

10K

5K

Trail

View details for race Run for the Pumpkins Trail Run

Forbidden Forest 30 Hour Ultra

Stratford, CT

Saturday, October 3rd, 2026

Trail

View details for race Forbidden Forest 30 Hour Ultra

Tom Centinaro Memorial "Dam" Race

Wolcott, CT

Saturday, October 17th, 2026

Trail

View details for race Tom Centinaro Memorial "Dam" Race

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

Storybook Half Marathon

Stratford, CT

Saturday, November 21st, 2026

Half

Trail

View details for race Storybook Half Marathon

Frosty Forest 5k

Stratford, CT

Saturday, December 19th, 2026

5K

Trail

View details for race Frosty Forest 5k

Explore more in Old Saybrook, CT

Distances:

5K 10K Half Marathon Marathon

Months:

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Tags:

Trail Boston Qualifiers Fast Courses

State:

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