4 walking events in Dutchess County, New York

From big races to Saturday morning group runs—find walking events and connect with the local endurance sports community.

• AEF May the Course Be With You 5K [arlingtonschools.org] [Register at runsignup.com]
  • Subscribe to My Calendar (sign in required)

  • ---

  • Download single event

  Sat, May 02, 2026 at 8:30 AM

  Description

  ▼ Show more Show less

  🚀 May the Course Be With You 5K Community Festival

  May 2, 2026

  Two days away from the 4th... be with you

  📍 Location: Union Vale Middle School

  1657 E Noxon Rd, Lagrangeville, NY 12540

  🕒 Event...

  🚀 May the Course Be With You 5K Community Festival

  May 2, 2026

  Two days away from the 4th... be with you

  📍 Location: Union Vale Middle School

  1657 E Noxon Rd, Lagrangeville, NY 12540

  🕒 Event Timeline:

  8:30 AM – Kids Mini Race

  8:45 AM – 1-Mile Fun Run/Walk

  9:00 AM – 5K Race Start

  8:45 AM – 1:00 PM – Family Festival

  🌌 Event Overview

  Get ready to launch into an unforgettable, intergalactic morning of movement, music, and community spirit. The May the Course Be With You 5K Community Festival brings neighbors, families, and friends together for a high-energy wellness experience designed for all ages and abilities.

  Whether you are racing for a personal best, walking with friends, or cheering from the sidelines, this event is about showing up, having fun, and supporting students in our district.

  ✨ Intergalactic costumes are highly encouraged.

  🏆 Prizes will be awarded for Best Costume.

  🏃‍♂️ Race Experiences

  5K Run (9:00 AM)

  A professionally timed 5K course perfect for competitive runners and casual participants alike.

  1-Mile Fun Run/Walk (8:45 AM)

  An inclusive, family-friendly route designed for all ages and fitness levels.

  Kids Mini Race (8:30 AM)

  A high-energy lap created just for our youngest participants to kick off the morning with excitement.

  Special Mini Race Perks!

  Thanks to Hudson Valley’s Best:

  🎂 All Mini Race participants will be entered for a chance to win a FREE Birthday Party valued at $500

  🤸‍♂️ Participants will also receive FREE trial passes to experience the fun at Hudson Valley’s Best

  Register early and save. Prices increase after May 1!

  🎉 Family Festival (8:45 AM – 1:00 PM)

  After the races, stay and celebrate at our community festival featuring:

  Music

  Photo stations

  Costume contest

  Food trucks

  Local vendors

  Interactive activities and more

  💫 Why Your Participation Matters

  This event promotes health, wellness, and connection while supporting scholarships for students in our district.

  Every step, every dollar, and every smile helps fuel bright futures.

  We cannot wait to see you at the starting line. May the course be with you.

  1 Miles 5k Fun Run Run Walk

  1657 E Noxon Road, Dutchess County, New York, 12540, United States
  OpenStreetMap Google Maps
• EDRRC - Eagle Run 5K Run/Walk and Kids Run [edrrc.org] [Register at runsignup.com]
  • Subscribe to My Calendar (sign in required)

  • ---

  • Download single event

  Sat, May 30, 2026 at 9:30 AM

  Description

  ▼ Show more Show less

  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

  3.1 Miles 5k Fun Run Kids Run Walk

  37 Shepherds Way, Dutchess County, New York, 12514, United States
  OpenStreetMap Google Maps
• The Robert Van Tassel “Live the Dash” Memorial 5k sponsored by Chelsea Fire Company [runsignup.com]
  • Subscribe to My Calendar (sign in required)

  • ---

  • Download single event

  Sun, Aug 09, 2026 at 8:30 AM

  Description

  ▼ Show more Show less

  An annual 5K run/walk and kids 1 mile race on the streets of Chelsea, NY located in the town of Wappingers ( NOT the Chelsea in NYC) to benefit the Chelsea Fire Company, and The Robert VanTassel...

  An annual 5K run/walk and kids 1 mile race on the streets of Chelsea, NY located in the town of Wappingers ( NOT the Chelsea in NYC) to benefit the Chelsea Fire Company, and The Robert VanTassel “Live the Dash” scholarship. Given to 2 Beacon High School Seniors, who show sportsmanship, integrity, and 100% commitment to his/her running goals.

  In 2023, we changed the name of the race to The Robert Van Tassel Live the Dash 5k. Bobby was the race coordinator from the beginning. He ran the race every year and gave the medals out at the end. He was the Fire District Commissioner, past chief, and held every office over the 40 years he served CFD. He passed on October 20, 2022. Running was his passion. He ran until his very last breath. We continue this race in his honor. “LIVE THE DASH”!! The race starts and ends at the fire station on Liberty St. and takes you along the Hudson River. Want to run with friends or family, sign up together!

  1 Miles 3.1 Miles 5k Run Walk

  16 Liberty Street, Dutchess County, New York, 12512, United States
  OpenStreetMap Google Maps