Fleet Feet's 2026 "Earn Your Square" Run/Walk Powered by Brooks

More races nearby

• PK5K Wellness Run/Walk [runsignup.com]

  Sat, Apr 25, 2026 at 10:00 AM

  Description

  ▼ Show more Show less

  We, The Poughkeepsie Run Team, comprised of The City of Poughkeepsie Softball/ Baseball League, As One Flight, LLC, and the City of Poughkeepsie Youth Division, acknowledge the critical importance of...

  We, The Poughkeepsie Run Team, comprised of The City of Poughkeepsie Softball/ Baseball League, As One Flight, LLC, and the City of Poughkeepsie Youth Division, acknowledge the critical importance of prioritizing physical mental health and wellness in our society. We are dedicated to empowering individuals of all ages, including youth and future generations, to cultivate and sustain optimal mental well-being.

  Our mission is to equip them with the necessary tools and resources to thrive in today's world. Through education, support, and advocacy, we are committed to fostering a culture of holistic wellness, ensuring that every individual has the opportunity to lead a fulfilling and balanced life.

  2nd Annual PK 5K Run

  The 2nd Annual PK 5K Run takes place in Poughkeepsie, NY on April 25, 2026, at 10:00 a.m., bringing the community together to promote physical health, mental wellness, and youth development.

  Hosted by the Poughkeepsie Run Team—a collaboration between the City of Poughkeepsie Youth Baseball & Softball League, As One Flight LLC, Finish Strong LLC, and the City of Poughkeepsie Youth Division—the PK 5K is dedicated to encouraging wellness for all ages, with a strong focus on supporting youth and families.

  Following a successful inaugural race, funds raised helped provide a $500 Wellness Grant to a local family, demonstrating the meaningful community impact of this event.

  The event includes:

  • Youth Mile Run/Walk

  • 5K Run/Walk (Ages 13+)

  All fitness levels are welcome—runners, walkers, families, and first-time participants are encouraged to join.

  Race Day: April 25, 2026

  Start Time: 10:00 a.m.

  Rain Date: May 2, 2026

  943 m from City of Poughkeepsie
  City of Poughkeepsie, New York, 12601, United States
  OpenStreetMap Google Maps

  5k Run Walk

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

  Sat, May 30, 2026 at 9:00 AM

  Description

  ▼ Show more Show less

  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

  4.9 km from City of Poughkeepsie
  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

  ▼ Show more Show less

  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

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

  5k 10k Run Trail

• Locust Cider Run [runsignup.com]

  Sat, Jun 06, 2026 at 11:00 AM

  Description

  ▼ Show more Show less

  Join us for our first-ever 5K!

  Locust Grove Fruit Farm has been home to eight generations of the Kent family — a legacy made possible by the farmers who have cared to this land generation after...

  Join us for our first-ever 5K!

  Locust Grove Fruit Farm has been home to eight generations of the Kent family — a legacy made possible by the farmers who have cared to this land generation after generation. Farming is in our blood, and we’re committed to keeping that tradition alive for those who dream of continuing it.

  To give back to the community that has supported us at both the farm and the brewery, all proceeds from this race will benefit our first-ever Locust Grove Fruit Farm & Locust Grove Brewing Co. Scholarship. This scholarship will be awarded to a Marlboro High School senior planning to pursue a career in agriculture or a skilled trade.

  The 5K will take place in the town of Milton on June 6th at 11:00 AM, starting at the Locust Grove Pick Your Own Stand and finishing at our brewery. Celebrate with us, support a great cause, and enjoy a cold drink at the finish line as we give back to the community we love.

  5 km from City of Poughkeepsie
  199 North Road, Marlboro, New York, 12547, United States
  OpenStreetMap Google Maps

  3.1 Miles Run

• Dutchess County Classic [finishers.com]

  Sat, Sep 26, 2026

  Description

  Ready to take on a sports challenge in a stunning natural setting 🌳? The Dutchess County Classic in Wappingers Falls and Poughkeepsie awaits you with courses for all skill levels!

  922 m from City of Poughkeepsie
  City Of Poughkeepsie, New York, United States
  OpenStreetMap Google Maps

  5k 10k Half Marathon Run