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Trail races in Westchester & Hudson Valley (2026-27)

8 upcoming trail races in Westchester & Hudson Valley in the next 12 months. The next is Fall Run The Farm on Sunday October 25 in Katonah, from $24.

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• Sun25Oct

  Fall Run The Farm

  Sun Oct 25 · 8:30 AM · Katonah · Westchester & Hudson Valley

  1.1 miles5 milesTrail

  from $24Goes up Oct 24
• Sat7Nov

  Pocantico Hills Races

  Sat Nov 7 · 8:00 AM · Tarrytown · Westchester & Hudson Valley

  Half marathonMarathonTrail

  from $75Goes up Nov 6
• Sun22Nov

  Head for the Hilltop 5K + Kids Fun Run

  Sun Nov 22 · 9:00 AM · Yorktown Heights · Westchester & Hudson Valley

  5KTrail

  from $40
• Sat3Apr

  Big Bear SquaTCh North

  Sat Apr 3 · 9:00 AM · Bear Mountain · Westchester & Hudson Valley

  10KHalf marathonTrail

  from $45Goes up Dec 31
• Sun18Apr

  Try the Trail

  Sun Apr 18 · 9:00 AM · Katonah · Westchester & Hudson Valley

  1 mileTrail

  from $30Reg. closed
• Sun23May

  Spring Run The Farm

  Sun May 23 · 8:30 AM · Katonah · Westchester & Hudson Valley

  1.1 miles5 milesTrail

  from $20Goes up Feb 7
• Sat5Jun

  Squatch the Hook

  Sat Jun 5 · 9:00 AM · Valley Cottage · Westchester & Hudson Valley

  5K10KTrail

  from $35Goes up Apr 29
• Sat16Oct

  Big Bear SquaTCh South

  Sat Oct 16 · 11:00 AM · Tuxedo · Westchester & Hudson Valley

  10KHalf marathonTrail

  from $45Reg. closed