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  • Roxbury Road Race Series #13 [runsignup.com]

    Sat, May 30, 2026 at 8:30 AM

    Description

    3.9 Miles- Jeep Trail

    Active duty military/veterans and active first responders are encouraged to contact the race for a discount.

    24.1 km
    18 Apple Lane, Northwest Hills Planning Region, Connecticut, 06783, United States
    OpenStreetMap Google Maps

    3.9 Miles Run Trail

  • 52nd Annual Rooster Run [runsignup.com]

    Sat, Jun 13, 2026 at 8:00 AM

    Description

    T-SHIRT AND BIB AVAILABLE FOR PICK UP BEGINNING FRIDAY, JUNE 12TH STARTING 8 AM UNTIL 4 :30 PM.

    IF YOU REGISTERED after June 12 at 4 pm, your race number is only available on race day.

    WE ARE LOCATED...

    T-SHIRT AND BIB AVAILABLE FOR PICK UP BEGINNING FRIDAY, JUNE 12TH STARTING 8 AM UNTIL 4 :30 PM.

    IF YOU REGISTERED after June 12 at 4 pm, your race number is only available on race day.

    WE ARE LOCATED IN FAIRFIELD HILLS IN THE COMMUNITY CENTER AT 8 SIMPSON STREET.

    UNABLE TO PICK UP NO WORRIES, YOU CAN PICK IT UP THE DAY OF

    The Rooster Run/Walk will have a 5K & 10K certified Course (8:20AM START TIME). Your little chickens will also have a chance to run in our 100 yard dash (Little Chicks Dash- 8AM START TIME). The proceeds from these events will benefit the Newtown Scholarship Association.

    Make it a family event, bring your friends and cheer on your friends and family as they raise money for a great cause! Register by midnight June 13th before the price increase. Registration will close on June 13th at 7:30 am. All registration will be done online.

    The first 250 participants will receive a t-shirt.

    Newtown Scholarship investing in Newtown's youth!

    Rooster Run 5K Road Race Categories:

    • Top Male Finisher

    • Top Female Finisher

    • Divisions – top 3 overall finishers:

    • Male

    • 12 and under

    • 13 to 19

    • 20 to 29

    • 30 to 39

    • 40 to 49

    • 50 to 59

    • 60 to 69

    • 70 and over

    • Female

    • 12 and under

    • 13 to 19

    • 20 to 29

    • 30 to 39

    • 40 to 49

    • 50 to 59

    • 60 to 69

    • 70 and over

    10K

    Top Male Finisher

    Top Female Finisher

    Divisions – top 3 overall finishers:

    Male

    12 and under

    13 to 19

    20 to 29

    30 to 39

    40 to 49

    50 to 59

    60 to 69

    70 and over

    Female

    12 and under

    13 to 19

    20 to 29

    30 to 39

    40 to 49

    50 to 59

    60 to 69

    70 and over

    The 10K course is one small loop followed by three long loops around the paved Newtown Hills trail.

    10.4 km
    Keating Farms Ave., Newtown, Connecticut, 06470, United States
    OpenStreetMap Google Maps

    5k 10k Run Trail Walk

  • Roxbury Road Race Series #16 [runsignup.com]

    Sat, Jun 20, 2026 at 8:30 AM

    Description

    4.2 Miles- Wellers to Jeep Trail Loop

    Active duty military/veterans and active first responders are encouraged to contact the race for a discount.

    24.1 km
    18 Apple Lane, Northwest Hills Planning Region, Connecticut, 06783, United States
    OpenStreetMap Google Maps

    4.2 Miles Run Trail

  • Ridge Reaper Trail Runs [steependurance.com] [Register at ultrasignup.com]

    Sat, Aug 01, 2026

    19.9 km
    Meadow Parking Lot, Town of Lewisboro, New York, 10518, United States
    OpenStreetMap Google Maps

    25k 50k Run Trail Ultra

  • Where the Pavement Ends Single & Double Loop [runsignup.com]

    Sun, Sep 20, 2026 at 7:00 AM

    Description

    Where the Pavement Ends Trail Races are set for Sunday, September 20, 2026

    You can do one loop of the course or do two loops for a “Pavement Double”!

    The race starts and ends at Lake Windwing...

    Where the Pavement Ends Trail Races are set for Sunday, September 20, 2026

    You can do one loop of the course or do two loops for a “Pavement Double”!

    The race starts and ends at Lake Windwing ballfields in Ridgefield, CT. The 4.25-mile course (single loop) begins at 7:30 AM, and the 8-miler (approximate double loop) begins at 7:00 AM. The course runs through the Hemlock Hills/Pine Mountain open space areas. It's technical, rocky, and sublime. If you are not an experienced trail runner, we recommend choosing the 4.25-mile course.

    This race is part of the Trail Mix Series—Westchester-Fairfield Trail Mix Series: a series of seven trail races. The results from all the races are combined to determine a series winner and award special prizes.

    10.6 km
    South Shore Drive/Lake Windwing, Ridgefield, Connecticut, 06877, United States
    OpenStreetMap Google Maps

    4.3 Miles 8.2 Miles Run Trail

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