Found 308 races near Litchfield County, CT

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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
3
OCT
17

Ivoryton, CT
• 51.0 miles
$35
The Ivoryton Pumpkin Chase is a 5K Road/Trail Race and a Kiddie Pumpkin Fun Run (age 7 and below) to benefit the Ivoryton Library and takes place in peak foliage season of southern New England....
23
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
5
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 -...
41
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
4
OCT
17

Middlebury, CT
• 48.7 miles
High School Cross Country Meet
5
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
31
OCT
18

Bristol, CT
• 32.5 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
7
OCT
18

Hartford, CT
• 23.8 miles
$30
6
OCT
18

TRUMBULL, CT
• 35.7 miles
$20 -$40
Great Pumpkin Classic in TRUMBULL, CT - historic downtown race course featuring great community spirit and atmosphere
5K
67
OCT
18

Valley Cottage, NY
• 54.6 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
5
OCT
18

Belchertown, MA
• 14.9 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
1
OCT
18

TRUMBULL, CT
• 34.4 miles
$16 -$40
WELCOME TO THE 36th CONSECUTIVE YEAR OF THE GREAT PUMPKIN CLASSIC!!!    PLEASE HELP US CELEBRATE OUR AMAZING EVENT- STARTED IN 1991 BY OUR RACE DIRECTOR MARTY SCHAIVONE - A BIOLOGY TEACHER AT THS...
5K
4
OCT
18

Ridgefield, CT
• 35.1 miles
$28 -$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, and...
5K Half Marathon
45
OCT
18

Salisbury, CT
• 47.0 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
34
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
17
OCT
24

Cheshire, CT
• 40.5 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
5
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
3
OCT
24

Ludlow, MA
• 6.5 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
19
OCT
25

East Hampton, CT
• 38.2 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
5