Found 308 races near Litchfield County, CT

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NOV
26

Hamden, CT
• 32.5 miles
$40
Please join us on Thanksgiving for our Annual Run Turkey Run 5K. A long-standing Thanksgiving tradition in Hamden, there is no better way to start your Thanksgiving Day than running or walking a...
5K
35
NOV
26

Redding, CT
• 62.7 miles
$30 -$40
The Great Turkey Escape 5K road race and 3/4 mile kids run. We will spoil our runners with a long sleeve tech shirt, an embroidered winter beanie (hat), embroidered running gloves and a...
1K 5K
34
NOV
26

Valhalla, NY
• 35.8 miles
$14 -$52
Join the Thanksgiving Day tradition at the Westchester Turkey Trot 10K & 5K Run/Walk presented by Northwell Orthopedics. Valhalla, NY Use #TurkeyTradition to share your photos! Event times,...
5K 10K
52
NOV
28

New York City, NY
• 43.9 miles
$30 -$45
Get Ready to Wobble Before You Gobble! 🦃 Join us for the annual Thanksgiving Gobble Trot! Before you dive into the turkey and stuffing, enjoy the holiday with your family, friends, and fellow...
1m 5K 10K Half Marathon
6
DEC
5

Bethlehem, CT
• 8.7 miles
$30
Santa Made Me Do It! is a 5K road race, 2 mile walk and 1/4-mile kids fun run on December 5, 2026 in Bethlehem, CT. This race is organized by The First Mile and will be held in conjunction with...
2m 5K
34
DEC
12

New York City, NY
• 50.1 miles
$30 -$45
🌅Run at Sunrise with pretty scenic views!Start your day — and your journey — with a breathtaking sunrise and fellow runners chasing greatness.   Overview:Run will sell-out QUICK! We will close...
1m 5K 10K Half Marathon
3
DEC
19

Stratford, CT
• 36.0 miles
Frosty Goes 5k Off Road Santa says you could win this!!! Join us for the FROSTY 5K on December 19, Saturday, with a start time of 10 AM. This exciting frosty 5k run takes place at the Town of...
5K
8
DEC
20

Madison, CT
• 47.3 miles
$45 -$55
Get ready for this year’s Jingle Bell Run, the original festive race for charity brought to you by the Arthritis Foundation. Wear your favorite holiday gear, and let's jingle all the way toward a...
5K
DEC
26

New York City, NY
• 50.1 miles
$30 -$45
🎉 Start Your Year on the Right Foot! 🏃‍♀️🏃‍♂️Join the New Year's Run - New Beginnings Starts Today!Kick off the new year with energy, excitement, and a community of runners ready to chase their...
1m 5K 10K Half Marathon
4
JAN
1

Brookfield, CT
• 20.4 miles
$30
RACE DAY REGISTRATION IS AVAILABLE ONSITE STARTING AT 9:30 A.M. Join us as we host the 39th Annual New Year's Day Run for Sight 4-Miler! All monies raised go to supporting the Connecticut Lions...
4m
44
JAN
1

Westfield, MA
• 25.1 miles
$35 -$40
The Boys & Girls Club, along with the volunteer organizers of the Westfield Half & 5k, host Gordy's First Race, a 5k and 10k race on New Years Day each year, in memory of long time runner and...
5K 10K
67
JAN
10

Barkhamsted, CT
• 17.8 miles
This is a hand timed, club run through beautiful Barkhamsted, CT.  It starts at Matthies Grove Parking area, People's State Forest, 106 East River Road 06063.  The course consists of rolling...
17m
16
JAN
31

Milford, CT
• 38.5 miles
$20 -$30
We are excited to announce the 46th annual Winter Wonderland 5 Miler Sunday, January 31, 2027 at 9:30 am!!!! Details to come in Fall 2026! The proceeds and donations of this event fund...
2m 5m
50
MAR
7

New Haven, CT
• 35.6 miles
$30 -$39
The flat 5K course runs travels starts and finishes in front of the historic New Haven Rock and Roll venue Toad’s Place. Celebrate St. Patrick’s Day after the race at Toad’s Place with an...
5K
34
MAR
13

Essex, CT
• 52.7 miles
$33 -$38
Celebrate St Patrick's Day and try to Catch A Leprechaun in support of the Region 4 Education Foundation. The race route follows a 5K course around the town of Essex Registration & Race Schedule...
5K
26
MAR
20

Peconic, NY
• 64.2 miles
$15 -$50
Like Running or Walking?  Love Wine?  This race is for you!  Join us on Saturday, March 20, 2027 at 9:00am for an exciting annual event that features the amazing scenery and landscape of the...
5K
3
APR
4

Cross River, NY
• 38.1 miles
$14 -$35
SPONSORS Thank you to our wonderful sponsors! We are always looking for additional sponsors for the community races! We truly appreciate the sponsors who enable us to host a fun and competitive...
4K 5K
2
APR
11

Millbrook, NY
• 34.2 miles
$80
Eastern Dutchess Road Runners Club 7th Annual  Millbrook Marathon Sunday, April 11, 2027 Race day packet pick-up opens at 6:30 am Race Starts at 7:30 am Sharp (Rain or Shine) 6 hour time limit  ...
Marathon
8
APR
18

Stamford, CT
• 50.9 miles
Stamford Run Club 5k/10k/Half Marathon 2026
Half Marathon
6
APR
25

Cross River, NY
• 38.9 miles
$58
   The Leatherman's Loop is put on by Leatherman's Loop Races.  Other races to check out:  SPRING Run the Farm (May 17, 2026) • Fire Tower Trail Half Marathon & 10k (June 7, 2026) • FALL Run the...
3