Found 274 races near Litchfield County, CT

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JAN
30

New York City, NY
• 50.1 miles
$30 -$45
☕️ 🏃‍♂️ ☕️ 🏃‍♂️ ☕️ 🏃‍♂️ For all the Coffee Lovers, this run is for you! You’ll love the shirt we send you. Set a goal, bring a friend, and join this super fun 5K/10K/13.1 Half-Marathon! The first...
1m 5K 10K Half Marathon
20
JAN
30

New York City, NY
• 50.1 miles
$30 -$45
 🎈🍩 Donut Mind If I Do! 🏃‍♂️💨 Get ready for a race day fueled by laughter, community, and a shared love for the world's best treat! 🍩✨ The 2027 Run for Donut is the ultimate celebration for...
1m 5K 10K Half Marathon
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
73
FEB
13

New York City, NY
• 50.1 miles
$30 -$45
 🔥 Run Now, Chocolate Later! 😋🏆Who says you can't have your chocolate—and run it too? The 2027 Run for Chocolate is coming, and it’s sweeter than ever! 🎉Rally your friends, set your pace for our...
1m 5K 10K Half Marathon
16
FEB
13

New York City, NY
• 50.1 miles
$30 -$45
💘 Celebrate love and fitness this Valentine’s Day with our charming Valentine's Run! Whether you’re running solo, with a partner, or with friends, this event is all about spreading love and joy. ...
1m 5K 10K Half Marathon
15
FEB
28

Warren, CT
• 6.0 miles
$36 -$50
Join us for an epic 7.8 mile loop of picturesque Lake Waramaug - this annual winter tradition attracts hundreds of area runners. Powered by a team of more than 75 volunteers, we're committed to...
19
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
53
MAR
13

Essex, CT
• 53.6 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
49
MAR
20

Peconic, NY
• 64.2 miles
$15 -$50
A vineyard 5K with a wine glass, finisher medal, and a pour of wine at the finish.
5K
21
MAR
20

New York City, NY
• 77.2 miles
$30 -$45
 ✨🌄 Chasing the Sun, Crushing Goals! 🏃‍♀️💨Welcome to the 2027 Sunrise Marathon 5K/10K/13.1! There is no better way to start your day than stepping up to the starting line just as the world wakes...
1m 5K 10K Half Marathon
MAR
27

Valley Cottage, NY
• 72.8 miles
$150 -$299
A Race Series Designed by Runners, for RunnersIn 2021, the coaches of the McKirdy Trained online coaching platform created the McKirdy Micro Marathon series to give athletes an opportunity to...
13
MAR
28

Valley Cottage, NY
• 72.8 miles
$150 -$250
A Race Series Designed by Runners, for Runners In 2021, the coaches of the McKirdy Trained online coaching platform created the McKirdy Micro Marathon series to give athletes an opportunity to...
28
APR
4

Cross River, NY
• 59.6 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
33
APR
10

New York City, NY
• 50.1 miles
$30 -$45
🥯🏃‍♂️ Run for the carbs. Stay for the bagels. Love running? Love bagels? This one’s for you. Whether you’re chasing a workout or just here for the carbs, this run is all about balance, fun, and...
1m 5K 10K Half Marathon
APR
11

Millbrook, NY
• 20.5 miles
$80
Seventh annual 26.2-mile USATF-certified, Boston-qualifying road marathon in Millbrook, NY.
Marathon
30
APR
18

Stamford, CT
• 50.9 miles
Stamford Run Club 5k/10k/Half Marathon 2026
Half Marathon
21
APR
24

New York City, NY
• 50.1 miles
$30 -$45
 ☕️ 🏃‍♂️ ☕️ 🏃‍♂️ ☕️ 🏃‍♂️ For all the Coffee Lovers, this run is for you! You’ll love the shirt we send you. Set a goal, bring a friend, and join this super fun 5K/10K/13.1 Half-Marathon! The...
1m 5K 10K Half Marathon
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...
13
MAY
1

Granby, CT
• 27.6 miles
$40 -$55
The annual Granby Road Race will take place on Saturday, May 1, 2027. One of Connecticut’s oldest and most historic road races, the 10K features a rolling, scenic course that winds along local...
1m 5K 10K
MAY
1

Haydenville, MA
• 51.2 miles
$20 -$30
Takesplace on Saturday, May, 2027, at 5 Bridge St, Haydenville, MA. The event begins at 0900 and supports local veterans through registration. It features a 5K run/walk to raise funds for...
1m 5K
19