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.
Dutchess County
4 events in Dutchess County-
Sat, Mar 14, 2026 at 9:00 AMSee full details
Eastern Dutchess Road Runners Club
5th Annual St. Patrick's 5K Run/Walk
Date: Saturday, March 14, 2026
Time: 5K starts at 9:00 AM sharp (Rain or Shine)
Packet Pickup: Available beginning at 8:00 AM on race day
All net proceeds and donations will be donated to the Lions Club Inc. of Dover, NY.
The race will begin and conclude at JH Ketcham Memorial Park in Dover Plains. The course will take place on town roads featuring a few small rolling hills. Afterward, we will provide refreshments and Shamrock Shakes!
The overall awards will be presented at 10 a.m.
Giveaways:
Finisher medal guarantee if signed up by March 7th 2026.
Registration:
$25 for Non-Members
$20 for Members
Race Day: $30 (Cash Only & No Giveaways)
Discounted prices are available for club members. Become a member at EDRRC.ORG
Awards:
Top Overall Male, Female, and Non-Binary finishers, plus 1st 2nd and 3rd place in each age group:
Age Groups: Up to 9, 10–14, 15–19, 20–29, 30–39, 40–49, 50–59, 60–69, 70+
Location:
J H Ketcham Memorial Park
46 Ketcham Pk
Dover Plains, NY 12522
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Sat, May 02, 2026 at 8:30 AMSee full details
🚀 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.
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Sat, May 30, 2026 at 9:30 AMSee full details
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:
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Up to 9
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10-19
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20-29
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30-39
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40-49
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50-59
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60-69
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70+
Location:
37 Shepherds Way
Clinton Corners, NY 12514
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Sun, Aug 09, 2026 at 8:30 AMSee full details
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!