Found 274 races near Litchfield County, CT

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OCT
25

Kent, CT
• 11.2 miles
$5 -$50
For fifty years, runners have gathered in Kent on a crisp autumn morning to celebrate fitness, friendship, community, and fun. What began as a small local race has grown into Kent's largest...
5m
9
OCT
25

Marlborough, CT
• 41.4 miles
$30 -$35
MARLBOROUGH LIONS CLUBMasquerade 5KSunday, October 25th, 2026 @ 10:30AMBLISH PARK, MARLBOROUGH CT.Register by Sunday 10/11/26 to guarantee a t-shirtPrizes are: Medallions for Top Male/Female...
5K
22
OCT
25

WESTON, CT
• 46.4 miles
$10 -$80
Weston Kiwanis 15th Annual Reservoir Run - Half Marathon, 5K, Kids Fun Run & Family Stroll If you participated in Reservoir Run events in the past, you know how scenic and wonderful they are. If...
5K Half Marathon
74
OCT
25

Meriden, CT
• 28.2 miles
$25 -$40
Join us for the 4th annual Run The Runway 5k and Kids Fun Run at the Meriden Markham Airport, a unique opportunity to run, jog, and walk on the runway! The 5K race route will begin on the Meriden...
5K
30
OCT
25

Valley Cottage, NY
• 41.7 miles
$51 -$66
A flat, fast USATF certified half-marathon around Rockland Lake in New York.
Half Marathon
53
OCT
28

Hamden, CT
• 32.3 miles
Hamden Hall XCountry Middle School Invitational
23
OCT
30

Litchfield, CT
• 4.3 miles
High School Cross Country Meet
21
OCT
31

Milford, CT
• 38.5 miles
$25 -$37
Join us for the 15th Annual Milford Trick or Trot 5K Run/Walk to benefit The Beth-El Center in Milford. The Beth-El Center is a recognized leader in caring for and meeting the needs of the hungry...
5K
22
OCT
31

Valley Cottage, NY
• 54.6 miles
$40
The Rockland Road Runners To Infinity & Beyond Halloween 5K will be a fun event for kids and adults. The money raised will go to the Jordyn Seiden Memorial Fund which will benefit kids who...
5K
13
OCT
31

Collinsville, CT
• 18.2 miles
$30
We are proud to host the Annual Collinsville Trick or Trot! RESULTS WILL BE POSTED THIS YEAR! THE RACE IS NOW USATF CERTIFIED! USATF CERTIFICATE # CT20019JHP This race is an event to raise funds...
36
OCT
31

Hamden, CT
• 32.3 miles
Hamden Hall X-Country CISAC League Race October 31
29
OCT
31

Wappingers Falls, NY
• 35.4 miles
$10 -$35
IN OUR 12TH YEAR!!!  THE ORIGINAL HALLOWEEN RUN FOR DUTCHESS COUNTY!!  THE ONE AND ONLY! Do you love running, walking and physical activity? How about in a costume!? Well then couple that with...
1K 5K
40
OCT
31

Middlefield, CT
• 32.9 miles
$30 -$55
Join us for the 4th annual Lyman Orchards Pie Run which offers 5K and 5 mile distance options through our hilly orchards and the Middlefield community! Proceeds benefit local Veterans and the...
5K 5m
28
NOV
1

LeRoy, IL
• 19.7 miles
$44 -$80
Certified, chip-timed half marathon in Central Illinois with fall colors and no single-use plastics.
Half Marathon
22
NOV
1

Valley Cottage, NY
• 54.4 miles
$30
Join us on November 1st for NAMI Rockland’s 5K annual Run / Walk for Wellness to raise money for local programs and services that promote mental health awareness and end the stigma. Runners and...
5K
19
NOV
1

Cross River, NY
• 54.6 miles
$46 -$55
The Raven Rocks 10k Trail Run is BACK for NOVEMBER 8, 2026! Woo hoo! We have also brought back the 100k Raven Challenge with all of the fun elements from last year -- plus we're looking to add a...
10K 100K
116
NOV
1

Amherst, MA
• 57.4 miles
A 10 mile point-to-point race from Amherst to Northampton on the paved Norwottuck Trail, plus a flat NoHo 5K.
5K
46
NOV
6

Litchfield, CT
• 3.4 miles
High School Cross Country
18
NOV
7

Coventry, CT
• 49.1 miles
$35 -$45
A run, walk, and ruck event in Coventry, CT honoring veterans, with 100% of proceeds to CT veterans.
3m 4m
42
NOV
7

Broad Brook, CT
• 38.3 miles
$20
                                              East Windsor Veterans Day 5K Road Race                                                                              Location: 11 Rye St - Broad Brook...
5K
18