Found 96 races near Chester, VT

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SEP
26

Orwell, VT
• 64.4 miles
$20 -$25
Limited Spots Available – Register Now! To ensure a high-quality experience for all participants, we are capping registration for The Silver Heist & Little Bandits Bolt at 150 runners. Once we...
5K
49
SEP
26

Newport, NH
• 22.2 miles
$25 -$30
🎶 Race Information🏃  🕺Get ready to lace up your running shoes and travel through time at the Through the Decades 5K! This fun and festive 5K combines paved road running with the beauty of the...
5K
4
SEP
26

Williamstown, MA
• 48.6 miles
$5 -$15
The Williamstown Community Chest Fun Run, sponsored by MountainOne, is a family-friendly community-centric event. Both the 5K and 1 mile Walk/Run are open to everyone, veteran or first-time...
1m 5K
10
SEP
27

Brownsville, VT
• 15.5 miles
$175 -$400
50-mile mountain bike and ultra-run race at Ascutney Outdoors, West Windsor, Vermont, benefiting Vermont Adaptive.
50K 50m
73
OCT
3

Bristol, NH
• 48.7 miles
10K Half Marathon Marathon
OCT
3

New Ipswich, NH
• 45.7 miles
$25
Scenic fall foliage 5K run/walk benefiting the Society of St. Vincent de Paul in New Ipswich, NH.
5K
62
OCT
4

Keene, NH
• 32.5 miles
$35 -$40
5K & 10K trail runs starting and finishing at the Keene Family YMCA in Keene, NH.
5K 10K
48
OCT
10

Milford, NH
• 56.1 miles
$10 -$40
Get ready to lace up your sneakers and join the excitement at the Boys & Girls Club of Souhegan Valley's Pumpkin Festival 5K & Kids Fun Run! Whether you're a seasoned runner or just in it for the...
1m 5K
5
OCT
10

Lebanon, NH
• 31.4 miles
OCT
10

New Ipswich, NH
• 48.7 miles
An endurance challenge that traverses the Commonwealth of Massachusetts following the Appalachian Midstate Trail during the peak of Autumn. The idea the for Midstate Massive Ultra Trail (MMUT)...
28
OCT
10

Warner, NH
• 39.2 miles
$25 -$40
A 5K race held during the annual Warner Fall Foliage Festival in Warner, NH.
5K
20
OCT
12

Stratton, VT
• 18.7 miles
$75
0ver $1,600 prizes The North Face Race to the Summit  is on Monday, October 14th, at 9:30am • Distance - 2.18 miles • Vertical climb: 2003 feet • Pre-register -$75.00 • Race Day registration -...
18
OCT
17

Brookline, NH
• 59.2 miles
OCT
17

Orange, MA
• 49.8 miles
$15
📅 Saturday, October 17, 2026 🕧 9:00am 📍 Ralph Mahar Regional High School - 507 South Main St. Orange, Ma 01364 ✨Looking to give back to the community? Here is your chance! Join Mahar Cancer Fund,...
5K
5
OCT
17

Whitehall, NY
• 45.4 miles
$140
Campout Ultra   October 17–18, 2026Champs Campground & RV Park | Whitehall, NY   How far can you go when motivation runs out?   The Campout Ultra is a timed endurance event held at Champs...
1
OCT
25

Enfield, NH
• 34.8 miles
5K 12K
OCT
25

Keene, NH
• 27.9 miles
$35 -$40
                                                     Sunday 25 October at 9am Yo-Yo-Yo!!   This is a race for all of you Yo-Yo's out there! Why Yo-Yo? Because that's exactly what you're going to...
17
OCT
31

Claremont, NH
• 14.9 miles
$1 -$30
🍩 NH Sneaker Brigade Donut Dash 2026 🍩🏃 Run. 🚶 Walk. 🍩 Eat Donuts. ❤️ Support a Great Cause THANK YOU TO the CSB FOUNDATION!! Their generous grant is allowing us to give away free and discounted...
5K
2
NOV
1

Henniker, NH
• 41.4 miles
$5 -$50
Hugs From Vets Trail 10K-ishRun for Those Who Served🍁 November 1 | Henniker, NH 🍁 Lace up your running shoes and join us for the Hugs From Vets Trail 10K-ish, a fun and challenging race that...
4
NOV
7

Keene, NH
• 28.0 miles
$20 -$45
Join us on Saturday, November 7th as the 12th Annual Monadnock Developmental Services Run~Walk~Smile once again joins forces with the Flutie 5K for Autism in Keene, NH! Come out and run, walk,...
1m 5K 10K
19