Found 274 races near Litchfield County, CT

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OCT
18

Bristol, CT
• 88.2 miles
$15 -$45
Sunday, October 18, 2026 57 years and still running. We will have 4 races this year  8 mile / 8K / 5K and the "Monster Mile" A Halloween Themed Event Our Title Sponsor for 2026 is Bristol Hospital
5K 8K 8m
25
OCT
18

Hartford, CT
• 96.0 miles
$30
19
OCT
18

TRUMBULL, CT
• 34.3 miles
$20 -$40
Great Pumpkin Classic in TRUMBULL, CT - historic downtown race course featuring great community spirit and atmosphere
1m 5K
94
OCT
18

Valley Cottage, NY
• 50.2 miles
$30 -$40
Lace up for Rockland's libraries! Join us for the 2nd Annual LARC in the Park 5K Run/Walk at Rockland Lake State Park on Sunday, October 18, 2026. Proceeds benefit the Library Association of...
5K
24
OCT
18

Belchertown, MA
• 134.2 miles
$20 -$35
Please join us for the 1st annual Runnin’ for Rett 5k and 1 mile walk. All proceeds are to benefit Rett Syndrome Angels charity. There will be a 5k run and 1 mile walk starting and ending next to...
1m 5K
11
OCT
18

Ridgefield, CT
• 39.0 miles
$33 -$75
October 18, 2026 Ridgefield Half-Marathon | 7:15 AM  Ridgefield 7-Miler | 7:15 AM  Iris Fund 5K | 7:30 AM   These races feature classic fall New England scenery. The races are beginner-friendly,...
5K Half Marathon
66
OCT
18

Salisbury, CT
• 21.2 miles
$45 -$55
Join us for year EIGHT of Connecticut's most monstrous 5k in the majestic hills of Salisbury Connecticut. Our third year as a USATF certified course, is specially dedicated this year to Peter...
5K
61
OCT
24

Brewster, NY
• 28.6 miles
$17 -$40
Join us for the Second Annual Brewster Teachers' Association 5K and inaugural 1 Mile Fun Run! This is a community event designed for runners and walkers of all ages and abilities! Set at our very...
1m 5K
34
OCT
24

Andover, CT
• 46.1 miles
$30 -$35
WHO: Anyone ages 0-100 WHAT:  Andover Norton Commission Trick or Trot 5K Run/Walk WHEN: October 24, 2026, Race bib pick ups and Halloween Costume contest start at 8:00 am WHERE: Andover...
5K
22
OCT
24

Cheshire, CT
• 25.1 miles
$17 -$38
The Cheshire Community YMCA and Cheshire Land Trust are partnering on a race around historic Ives Farm.  This all-ages run will wind through the fields and trails on the property, with the start...
5K
26
OCT
24

Modena, NY
• 43.9 miles
$20 -$40
Experience Hurds Family Farm after dark like never before! Put on your running shoes—or your favorite Halloween costume—and race through the orchards on a one-of-a-kind nighttime course featuring...
1K 2K 5K
21
OCT
24

Sleepy Hollow, NY
• 56.0 miles
$5 -$55
Enjoy a remarkable course that takes you through Historic Sleepy Hollow’s treasured sights, including a stretch along the Hudson River with views of the Headless Horseman Bridge, Sleepy Hollow...
10K
35
OCT
24

Ludlow, MA
• 48.6 miles
$25 -$35
      The Red Bridge Run Club is back for the 2nd Annual Ludlow Clocktower Classic 5k! Again this year, we are lacing up to support the incredible mission of the Ludlow Boys & Girls Club—and we...
5K
44
OCT
25

East Hampton, CT
• 42.2 miles
$25
5K for Ballet!Walk or run with us!  5K for Ballet is a timed fun run and untimed 2 mile walk hosted by the Creative Dance Center to support this year’s 44th annual Christmas show, Santa’s...
2m 5K
27
OCT
25

Hamden, CT
• 39.2 miles
$30 -$60
A 5K, 10K and 1-mile walk on the Farmington Canal trail benefiting CT veterans.
1m 5K 10K
75
OCT
25

Middletown, CT
• 33.9 miles
$30 -$40
Join us on Sunday, October 25th at 10 AM for the CT Law Enforcement Officers Memorial Run! All proceeds from the event benefit the National Law Enforcement Officers Memorial Fund and local law...
5K
122
OCT
25

Waterbury, CT
• 20.9 miles
$20 -$25
Thank you all for coming out to support the Crosby Sports Hall of Fame Fall into Fall 4k. The race proceeds raised nearly $900 for our scholarship fund. We look forward to seeing everyone and...
4K
30
OCT
25

Simsbury, CT
• 50.1 miles
A Halloween-themed flat 5K and walk in the Farmington River Valley for charity.
5K
68
OCT
25

Katonah, NY
• 42.3 miles
$23 -$47
FALL Run the Farm is a 5 mile trail race to be held at Muscoot Farm in Katonah/Somers, NY on October 25, 2026.  (There is also an upcoming SPRING running of this race on May 23, 2027 - sign up...
5m
24
OCT
25

Higganum, CT
• 40.4 miles
$20 -$35
Celebrate the Fall Season with this family friendly event! The Pumpkin Run benefits Haddam-Killingworth Youth and Family Services by supporting their programs for youth and families in the areas...
2m 5K 4m
19