Red Wing Trail Challenge

More races nearby

• Millbrook Marathon presented by the EDRRC [millbrookmarathon.com] [Register at runsignup.com]

  Sun, Apr 12, 2026 at 7:30 AM

  Description

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  Eastern Dutchess Road Runners Club

  6th Annual

  Millbrook Marathon

  Sunday, April 12, 2026

  Race day packet pick-up opens at 6:30 am

  Race Starts at 7:30 am Sharp (Rain or Shine)

  6 hour time limit

  Race...

  Eastern Dutchess Road Runners Club

  6th Annual

  Millbrook Marathon

  Sunday, April 12, 2026

  Race day packet pick-up opens at 6:30 am

  Race Starts at 7:30 am Sharp (Rain or Shine)

  6 hour time limit

  Race Description

  Join us on April 12th 2026 the sixth annual Millbrook Marathon presented by the Eastern Dutchess Road Runners Club. Come run 26.2 miles on our USATF Certified and Boston Qualifying course through the beautiful roads of Millbrook, NY. This might not be the flattest marathon you’ve ever run, but with the quiet country roads, rolling hills and the countless farms it sure will be the most scenic one!

  Take the first step and be a part of this exciting marathon by signing up, and when you take that last step across the line it will feel so rewarding.

  Course Description

  The course consists of rolling hills on mostly paved roads with some packed dirt roads mixed in. The course has about 2,400ft of elevation gain. See below for interactive map. The course is USATF certified and is a Boston Qualifying course. If any changes to water station locations or adjustments to course, updates will be posted closer to race day

  Interactive Course Map

  Race Cap 200 Participants

  Discounted Prices For Club Members

  Become a Member At EDRRC.ORG

  Post Race Info, Awards, and Giveaways

  Race overall Male & Female

  1st Place Male & Female in each age group

  Finisher medals guaranteed to the first 200 Sign Ups

  Race Tee-Shirt guaranteed for those signed up before (3/24/2026)

  Place

  Town of Washington Park and Pool

  3744 Route 44

  Millbrook, NY 12545

  11.6 km
  3744 Route 44, Village of Millbrook, New York, 12545, United States
  OpenStreetMap Google Maps

  26.2 Miles Marathon Run

• The Mommy Dash and Valley Pediatric Dentistry and Orthodontics 5K to Benefit the Terry D'Amato Scholarship Fund [runsignup.com]

  Sun, Apr 26, 2026 at 8:15 AM

  Description

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  Join us at this year's 5K and Kid Fun Run on Sunday, April 26th on the Dutchess County Rail Trail. We will continue our commitment to giving back to our community by donating a portion of our...

  Join us at this year's 5K and Kid Fun Run on Sunday, April 26th on the Dutchess County Rail Trail. We will continue our commitment to giving back to our community by donating a portion of our proceeds to the Terry D'Amato Scholarship Fund, honoring the life and legacy of Alicia's mom!

  The Kid Run (1/2 mile) will start at 8:15 am and the 5K (3.1 miles) will begin at 8:30 am. This race will be professionally timed and there will be prizes for 1st, 2nd and 3rd place males and females (ages 13 and up) as well as age group winners.

  Race day registration is from 7-7:30.

  All kids who participate in the fun run will receive a treat at the finish line.

  16.6 km
  Dutchess County Rail Trail, Village of Wappingers Falls, New York, 12590, United States
  OpenStreetMap Google Maps

  5k Fun Run Run Trail

• 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

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

  5k Run Trail 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

  10.4 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.

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

  5 Miles Run Trail