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  • Ion Bank Cheshire Road Races [cheshirehalfmarathon.org] [Register at runsignup.com]

    Sun, Apr 12, 2026 at 7:45 AM

    Description

    Half Marathon: The flat, fast course runs through Cheshire and Hamden, with considerable stretches running along the historic Farmington Canal Trail. Medals to half marathon finishers!

    5K: The 5K...

    Half Marathon: The flat, fast course runs through Cheshire and Hamden, with considerable stretches running along the historic Farmington Canal Trail. Medals to half marathon finishers!

    5K: The 5K course travels through scenic Cheshire neighborhoods, featuring few turns and a flat route. This course is perfect for all runners!

    Kids Fun Runs: courses run along the track!

    Enjoy live music, tech shirts and great post race food & drink!

    For more info visit www.cheshirehalfmarathon.org

    5.8 km from Cheshire
    Cheshire, Connecticut, 06410, United States
    OpenStreetMap Google Maps

    5k 13.1 Miles Fun Run Run Trail

  • Hamden Fest Half Marathon & 5k [teammossman.com] [Register at runsignup.com]

    Sat, Jun 06, 2026 at 8:30 AM

    Description

    The Hamden Fest Half Marathon & 5K will be held at Town Center Park on Saturday June 6th. The event includes a Half Marathon and 5K. The road races will offer runners and walkers some grass and paved...

    The Hamden Fest Half Marathon & 5K will be held at Town Center Park on Saturday June 6th. The event includes a Half Marathon and 5K. The road races will offer runners and walkers some grass and paved trail running.

    The Hamden Road race will kick off Hamden Fest. Hamden Fest will kick off at 11:00 am, with an extravaganza of events and activities in Town Center Park. The Hamden Regional Chamber of Commerce has partnered with the Town of Hamden to present this exciting event which will feature the Chamber's Annual Business & Community Expo; the Hamden Library Book Sale; Food Trucks and vendors; an Arts & Crafts & Antiques Fair; a Kids’ Zone by Hamden Youth Service Bureau; Entertainment by local musicians and more. Hamden Fest will run until 4:00 pm.

    Come enjoy this lively festival that brings together Hamden’s best – business, arts, cultural and educational communities.

    For more info about Hamden Fest, go to https://hamdenregionalchamber.com/promote/hamden-fest/.

    5 km from Cheshire
    Hamden, Connecticut, 06518, United States
    OpenStreetMap Google Maps

    3.1 Miles 5k 13.1 Miles Half Marathon Run Trail Walk

  • Gaylord Gauntlet [runsignup.com]

    Sat, Jun 13, 2026 at 8:00 AM

    Description

    The Gaylord Gauntlet 5K Trail and Obstacle Run is an annual event held on the 400-acre campus of Gaylord Specialty Healthcare in Wallingford, CT—a 137-bed long-term acute care hospital serving...

    The Gaylord Gauntlet 5K Trail and Obstacle Run is an annual event held on the 400-acre campus of Gaylord Specialty Healthcare in Wallingford, CT—a 137-bed long-term acute care hospital serving individuals recovering from life-changing injuries or illnesses. As a cornerstone fundraiser for the hospital, the event supports the Gaylord Sports Association, which is dedicated to enhancing the lives of people with physical disabilities through adaptive sports and recreation.

    The Gauntlet course features a mix of wooded trails and open fields, with 24 natural and manmade obstacles designed to challenge participants of all levels. The event is entirely planned, built, and run by Gaylord staff and volunteers, and includes a lively Festival Area with local vendors, live music, and food trucks.

    Open to runners of all abilities, the Gaylord Gauntlet is a true community celebration that brings together participants, families, and supporters for a day of fun, fitness, and purpose.

    Race Results can be found here: https://my.racewire.com/results/37904

    5.9 km from Cheshire
    50 Gaylord Farm Road, Wallingford, Connecticut, 06492, United States
    OpenStreetMap Google Maps

    5k Run Trail

  • Fishbein / YMCA Community Road Race [runsignup.com]

    Sun, Oct 04, 2026 at 9:00 AM

    Description

    Almost 50 years ago, Johanna Manfreda Fishbein started a tradition in Wallingford that would grow and change significantly over the years, bringing organizations throughout the town together to...

    Almost 50 years ago, Johanna Manfreda Fishbein started a tradition in Wallingford that would grow and change significantly over the years, bringing organizations throughout the town together to collaborate in an effort to support residents in need.

    The Wallingford Family YMCA is proud to continue this tradition as host of the annual Fishbein/YMCA Community Road Race on Sunday, October 4 in collaboration with Celebrate Wallingford.

    Hope to see you there!

    Note: Registration for this event is only available online and will remain open until 8:30AM on race day. Once you have registered, your race bib may be collected at advance packet pickup or on race morning. On Race Day, please allow plenty of time to park, check in and be ready to run at 9:00AM

    Entry Fees

    • 5K Race - 19+ Yrs - $30 before Jan 1, $35 from Jan 1-Oct 1, thereafter $40
    • Race shirt included for first 200 participants - sizes by availability
    • 5K Race - Under 19 - $5 (No shirt provided)

    • 1 Mile Youth Race - Under 14 (Parents, Guardians & Teachers are welcome too!) - $5

    • Healthy Living 1K Walk - $10 (FREE for LiveSTRONG at the Y participants)

    • Walk shirt included for first 100 walkers - sizes by availability
    • Note:
    • Reduced 5K entry fee for under 19 will be shown at the checkout.

    • Shirts will be available to purchase the day of the race for $10, if available.

    Event Schedule

    • Early Bib Pickup - Friday, October 2

    • Race Day Check In Opens at 7:00AM

    • Youth Race & Healthy Living Walk Start - 9:00AM

    • 5K Run Start - 9:10AM

    Awards

    • Awards will be given to top three overall M/F 5K Race winners

    • Top finisher in each 5K Race age category

    • 1-9 yrs

    • 10-14 yrs

    • 15-19 yrs

    • 20-29 yrs

    • 30-39 yrs

    • 40-49 yrs

    • 50-59 yrs

    • 60-69 yrs

    • 70-79 yrs

    • 80+ yrs

    • Please note that while Non-Binary is an entry option, no awards will be offered in this category
    8.4 km from Cheshire
    81 S Elm St, Wallingford, Connecticut, 06492, United States
    OpenStreetMap Google Maps

    1k 1 Miles 5k Run Walk

  • Abner Oakes III Veterans Run 5K & 10K [teammossman.com] [Register at runsignup.com]

    Sun, Oct 25, 2026 at 8:30 AM

    Description

    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...

    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 veterans and/or their spouses who have served our country faithfully and sacrificially. They do this by providing one day, no-cost home repairs through partnerships with and the generosity of individuals, civic organizations and corporations. They are committed to growing the organization and advancing the mission to the ever-increasing numbers of veterans both in Connecticut and nationwide.

    The Connecticut Chapter has provided no-cost home repairs to 276 Connecticut military and public safety veterans and/or their surviving spouses since 2012. Projects have been completed in 73 cities and towns throughout Connecticut. The organization will hit 286 projects by the end of the year.

    This event is dedicated to honor Abner Oakes III, a Navy Veteran and the founder of the Hamden Veterans Commission. In 2010 Abner was inducted into the Veterans Hall of Fame. Abner passed away May 29, 2021.

    9.9 km from Cheshire
    Farmington Canal Parking Lot, Hamden, Connecticut, 06514, United States
    OpenStreetMap Google Maps

    3.1 Miles 5k 10k Run

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