Fall Back into the Trails Series

More races nearby

• Peach Hill "Run For the Hill of It" 5K [runsignup.com]

  Sat, May 30, 2026 at 9:00 AM

  Description

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  Peach Hill "Run for the Hill of It" 5K: Saturday, May 30

  Rain date: Sunday, May 31

  This 5K cross-country run/walk takes participants along Peach Hill Park's mowed trails and hits the highest point in...

  Peach Hill "Run for the Hill of It" 5K: Saturday, May 30

  Rain date: Sunday, May 31

  This 5K cross-country run/walk takes participants along Peach Hill Park's mowed trails and hits the highest point in the Town of Poughkeepsie with beautiful views in all directions! Both runners and walkers are encouraged to participate and all ages are welcome. All proceeds to benefit the Friends of Peach Hill, a volunteer not-for-profit group that maintains and improves Peach Hill Park. Run for the hill of it!

  Register by May 1 for only $20 (plus fees). Registration from May 2-May 30 is $25 (plus fees). Race day registration is $30. No refunds.

  First 75 registrants get special Peach Hill 5K swag!

  Awards will be given out for top finishers as well as age group winners. Snacks afterwards!

  Race starts at 9am. Check-in begins at 8am.

  RESTRICTIONS: Please no bikes, dogs, or baby/jogging strollers

  10.2 km
  City of Poughkeepsie, New York, 12603, United States
  OpenStreetMap Google Maps

  5k Run Trail Walk

• EDRRC - Eagle Run 5K Run/Walk and Kids Run [edrrc.org] [Register at runsignup.com]

  Sat, May 30, 2026 at 9:30 AM

  Description

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  Eastern Dutchess Road Runners Club

  Upton Lake Christian School

  9th Annual Eagle Run 5K Run/Walk and Kids Run

  Date: Saturday, May 30th, 2026

  Time: Kids Fun Run starts at 9:00 AM & 5K starts at 9:30 AM...

  Eastern Dutchess Road Runners Club

  Upton Lake Christian School

  9th Annual Eagle Run 5K Run/Walk and Kids Run

  Date: Saturday, May 30th, 2026

  Time: Kids Fun Run starts at 9:00 AM & 5K starts at 9:30 AM (Sharp, Rain or Shine)

  Packet Pickup: Available starting at 8:00 AM on race day.

  All proceeds will be donated to Upton Lake Christian School.

  Registration Fees:

  $20.00 for Non-Members

  $15.00 for Members

  Race Day: $25.00 (Cash only & No giveaways)

  Free Kids Fun Run (for ages 10 and under); sign up on race day.

  Discounted prices are available for club members. Become a member at EDRRC.ORG

  Giveaways:

  Race T-shirt (Cutoff Date: May 10, 2026)

  Awards:

  Top Overall Male, Female, and Non-Binary Runners

  1st, 2nd, and 3rd place awards for Male and Female in each age group:

  • Up to 9

  • 10-19

  • 20-29

  • 30-39

  • 40-49

  • 50-59

  • 60-69

  • 70+

  Location:

  37 Shepherds Way

  Clinton Corners, NY 12514

  21.7 km
  37 Shepherds Way, Dutchess County, New York, 12514, United States
  OpenStreetMap Google Maps

  3.1 Miles 5k Fun Run Kids Run Walk

• The Big Run 5K/10K - Fleet Feet Poughkeepsie [runsignup.com]

  Wed, Jun 03, 2026 at 6:30 PM

  Description

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  Mark your calendars for June 3rd! Global Running Day isn't just a date on the calendar—it’s our favorite reason to bring the whole community together. The Big Run returns to the Dutchess Rail Trail...

  Mark your calendars for June 3rd! Global Running Day isn't just a date on the calendar—it’s our favorite reason to bring the whole community together. The Big Run returns to the Dutchess Rail Trail for another year of miles, smiles, and memories.

  We’re keeping the "fast and flat" course you crave but doubling down on the "After-Party." Expect more than just a finish line—we’re talking a full-blown festival with local eats, music, photo-op stations to flex those medals, and a few new surprises we’re keeping under wraps.

  6:30 PM: 10K start – Let’s go, long-distance crew!

  6:45 PM: 5K start – Squad up and hit the trail!

  Everything is chip-timed and USATF-certified, so you get the professional race feel with the neighborhood block party soul.

  Run Location: Gold's Gym LaGrange 258 Titusville Road Poughkeepsie, NY 12603 US

  10.2 km
  City of Poughkeepsie, New York, 12603, United States
  OpenStreetMap Google Maps

  5k 10k Run Trail

• Bowdoin Bushwhack Presented by Peace, Love, Trails [runsignup.com]

  Wed, Jul 15, 2026 at 6:30 PM

  Description

  Join us on Wednesday, July 15th at Bowdoin Park for the Bowdoin Bushwhack!

  Ramble through the brambles of beautiful Bowdoin Park. 5 miles of uphills, downhills, grass, rocks, trails- we have it all. If we could run you through the Hudson, we would, but that would be overkill.

  17.4 km
  85 Sheafe Road, Village of Wappingers Falls, New York, 12590, United States
  OpenStreetMap Google Maps

  5 Miles Run Trail

• Hilltopper Half Marathon [finishers.com]

  Sun, Jul 26, 2026

  13.6 km
  Village of Millbrook, New York, United States
  OpenStreetMap Google Maps

  Half Marathon Run