Found 274 races near Litchfield County, CT

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OCT
11

Holyoke, MA
• 42.4 miles
$35 -$50
Every mile makes a difference. Join us on October 11, 2026, at the beautiful Ashley Reservoir in Holyoke, MA, for the Race for Goals 5K & 1.5-Mile Walk. This community event supports the Paper...
1m 5K
3
OCT
11

Wallkill, NY
• 50.3 miles
$35
Race benefits the Shawangunk Valley Fire Company RACE DATE: Sunday October 11th, 2025RACE START TIME:  1-Mile Kids Run  8:30 A.M.      5-Miler  9:00 A.M.   LOCATION: Shawangunk Valley Fire House,...
5m
27
OCT
14

Watertown, CT
• 12.5 miles
NVL XC Championship
42
OCT
17

West Nyack, NY
• 58.3 miles
$25 -$40
The Happy Jack 5K is an annual, family-friendly walk/run honoring the life of our son, John Thomas “Happy Jack” Doyle. All proceeds benefit The Happy Jack Fund, which provides annual scholarships...
5K
21
OCT
17

Simsbury, CT
• 50.3 miles
$25 -$45
  OAH STRIDES 2026 Ready. Set. STRIDE. 📅 Saturday, October 17, 2026📍 Simsbury Meadows Performing Arts Center Join us for the 4th Annual OAH STRIDES Race & Family Fun Day — a community celebration...
5K 10K
10
OCT
17

Warren, CT
• 5.6 miles
$25
Town of Warren and Warren Land Trust's Cider Run/Walk 5k at Warren Woods!
5K
9
OCT
17

Pawling, NY
• 27.3 miles
$25 -$30
A Superhero 5K, Villain 10K, and free Kids Fun Run in Pawling, NY by the EDRRC.
5K 10K
64
OCT
17

Bolton, CT
• 42.6 miles
$30 -$35
"In every step we honor, in every mile we fight."-In loving memory of Stephen E. Foster   Race Info: Join us for the 2nd annual Harvest Hope 5K, dedicated to raising awareness and support for...
5K
21
OCT
17

Cornwall, NY
• 46.3 miles
$35 -$45
Enjoy majestic scenery and gorgeous autumn color as you run or walk past muskrat ponds, thru tall grass meadows, along wide grassy paths, elevated berm views, clearly marked wooded trails, and...
5K
22
OCT
17

Ivoryton, CT
• 51.0 miles
$30 -$40
The Ivoryton Pumpkin Chase is a 5K Road/Trail Race to benefit the Ivoryton Library and takes place in peak foliage season of southern New England. The course begins along Main Street for...
5K
53
OCT
17

Holyoke, MA
• 45.6 miles
$25 -$35
"She Leaves a Little Sparkle Wherever She Goes." Help us honor & remember forever 8 year old Maddie Schmidt from Southampton, MA, pay her magic forward and create something enduring and...
5K
13
OCT
17

Palmer, MA
• 55.7 miles
$30 -$35
Support Palmer High School students on their educational trip to Washington, D.C., by registering for our 5K Run or Walk. Every registration and donation helps make this memorable learning...
5K
10
OCT
17

Ellington, CT
• 41.2 miles
$30
Robert Tedford Memorial Road Races and Park Dedication 45 Sadds Mill Road, Ellington, CT 06029 Saturday, October 17, 2026 Race Day Registration available from 8 am to 9 am Races Start at 9:30 am ...
5K
22
OCT
17

Cornwall, CT
• 6.9 miles
$35
Join us for the region's premier human/dog race in the beautiful Cornwall Valley! The Little Guild’s Run & Wag 5K is a fun-filled day for runners, walkers, and their furry friends, featuring...
5K
20
OCT
17

Wolcott, CT
• 18.9 miles
$25 -$30
LOCATION: WOODTICK RECREATION201 NICHOLS ROAD WOLCOTT, CT 3.5 MILE TRAIL RUN/WALK ON THE SCENIC & FLAT MILL POND TRAIL SATURDAY - OCTOBER 17, 2026 RACE TIME - 10:00 am Race day Packet Pick Up -...
3m
73
OCT
17

Bridgeport, CT
• 41.9 miles
$10 -$45
Place, Date, and Time October 17th, 2026 8:30 am - Opening Ceremony 9:00 am - Race Start Time Ellsworth Park 166 Brewster Street, Bridgeport, CT __________________________________ Finish Line and...
5K
35
OCT
17

Middlebury, CT
• 17.5 miles
High School Cross Country Meet
21
OCT
18

Croton-on-Hudson, NY
• 49.9 miles
$12 -$45
Run/Walk where and when you'd like (virtually) between Oct. 10th and 17th -- or join us in-person at Croton Harmon High School, 36 Old Post Road South, on Oct. 18th! 5K RunFree t-shirt to first...
1m 5K 10K
57
OCT
18

Madison, CT
• 50.0 miles
$10 -$35
Join Us for the 2026 Run for The Cove in Madison!This meaningful event includes a 5K race, 2-mile memorial walk, kids' fun run, and family-friendly activities. It’s a special day to honor loved...
5K
40
OCT
18

Brookfield, CT
• 21.5 miles
$5 -$40
SUNDAY, OCTOBER 18TH! 5K Race Information: Come celebrate our 33rd year of the Brookfield Halloween 5K! This USATF certified chip-timed 5K will begin/end at the Brookfield Municipal Center, 100...
0m 5K
62