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OCT
18

Ridgefield, CT
• 31.2 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
• 35.4 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
• 31.3 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
• 8.2 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

Middletown, NY
• 59.3 miles
$35
Runners, walkers, volunteers and spectators will gather for a road race around South Centerville, New York. The event is being organized by the Knights of Columbus Council #16365 and will benefit...
5K 5m
OCT
24

Sleepy Hollow, NY
• 54.5 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
• 49.6 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
19
OCT
25

East Hampton, CT
• 26.8 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
OCT
25

Hamden, CT
• 13.4 miles
$30 -$60
Proceeds from this event will benefit the House of Heroes Connecticut.The mission of House of Heroes Connecticut (HOHCT) is to recognize, honor and serve Connecticut military and public safety...
1m 5K 10K
50
OCT
25

Middletown, CT
• 18.2 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...
91
OCT
25

Waterbury, CT
• 7.1 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
21
OCT
25

Simsbury, CT
• 30.7 miles
https://www.hartfordmarathon.com/donnys-dash/
5K
35
OCT
25

Englewood Cliffs, NJ
• 60.6 miles
$15 -$40
  9th Annual Englewood Cliffs 5K Hosted by:  Englewood Cliffs Recreation Department  Location:  Witte Field - Johnson Ave, Englewood Cliffs, NJ On Sunday, October 25, 2026, the Borough of...
5K
5
OCT
25

Katonah, NY
• 37.4 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.  Race start times:-8:30AM Kids race #1 (Age 7-12)-8:45AM Kids race #2 (Age 6 &...
5m
1
OCT
25

Marlborough, CT
• 33.6 miles
$25 -$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
2
OCT
25

Riverhead, NY
• 42.8 miles
$10 -$45
Race for the Greenway 5K Run / Walk - Presented by Long Island Wine Country  *Day of registration is card only!  Sunday, October 25th 2026Hallock State Park6062 Sound Ave, Riverhead, NY 11901  ...
5K
4
OCT
25

WESTON, CT
• 24.5 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
50
OCT
25

Meriden, CT
• 13.4 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
5
OCT
25

Valley Cottage, NY
• 51.9 miles
$51 -$66
Join us on Sunday, October 25, 2026 for the Tenth Annual Sri Chinmoy Half-Marathon at Rockland Lake State Park, featuring a scenic, "pancake flat" and fast 2.95 mile loop around the lake.  Set a...
Half Marathon
35
OCT
28

Hamden, CT
• 12.2 miles
Hamden Hall XCountry Middle School Invitational
5