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  • Distance: 12.1 km from Town of Lewisboro
    Sat, Jul 25, 2026 at 7:00 PM

    THE summer race with the best way to cool down, a margarita of course!

    Barbara Nevins and Southwest Cafe present the 20th annual Southwest Cafe Margarita 5k to benefit Ability Beyond. The yummy margarita you know and love will be waiting for you at the post-race fiesta! Race begins at 7pm!

    The Southwest Cafe Margarita 5K continues to support Ability Beyond, an organization dedicated to empowering every person, no matter their ability, to live, work and thrive as members of their community. The non-profit currently runs two residential programs in Ridgefield: Sunrise Cottage and Ritch Drive. Click on the "donation" button to find out more about Ability Beyond.

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    3.1 Miles5kRun via RunSignup
  • Distance: 1.6 km from Town of Lewisboro
    Sat, Aug 01, 2026
    25k50kRunTrailUltra via UltraSignup
  • Distance: 21.8 km from Town of Lewisboro
    Thu, Aug 20, 2026 at 6:30 PM

    Run or walk this 5K to support Ann's Place then kick back and enjoy one of Connecticut’s best post-race parties! Unwind and enjoy an outdoor barbecue, ice cold beer, refreshments, DJ and an awards ceremony. Bring your favorite picnic blanket or folding chair and enjoy the beautiful grounds of the Amber Room for the after-race celebration.

    This is an important fundraiser for Ann’s Place cancer support services. All proceeds go directly to Ann’s Place and help keep our doors open and our cancer support services FREE of charge to all those in need in our community. www.annsplace.org

    It’s easy and fun to fundraise! Create your own fundraising page or create a team page. Have some team building with your colleagues or friends or set your own personal goals. Waterworks, our presenting sponsor has friendly competitions between teams and have worn costumes to encourage donations. Other teams have created custom shirts and/or raised money in honor of someone, so many great ideas! We can't wait to see what everyone comes up with this year!

    Want to join in on the social media fun? Share your pictures and videos, while in training and during the race, via social media using the hashtag #runfromthesun5K

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    5kRunWalk via RunSignup
  • Distance: 22.6 km from Town of Lewisboro
    Sun, Aug 23, 2026 at 8:45 AM

    Unite to Fight!

    Childhood Hunger 5K Run/Walk

    Join Filling in the Blanks on August 23, 2026, at the Eighth Annual Unite to Fight 5K. The race will take place at Mill River Park located in Stamford, CT.

    In Fairfield County, more than 33,000 children are not sure where their next meal will come from. Most will get breakfast and lunch from school every weekday, but many will go from Friday lunch until Monday at breakfast without a decent meal. Founded in 2013, Filling in the Blanks is an organization that fills in those weekend gaps by providing each child in its program with a bag filled with healthy, easy-to-prepare food for the weekend. When the obstacle of food insecurity is removed, children experience increased academic achievement in school and greater opportunities for success in their lives. FITB continuously serves 10,000+ kids at over 200 sites throughout Fairfield, Westchester, and Putnam counties. FITB has also established four in-school pantries and in 2023 launched the Fresh Food On The Move mobile pantry that provides families with fresh produce, veggies, proteins and other staples, as well as health and wellness services.

    With your race registration, you will receive a Unite to Fight T-shirt.

    *T-shirts are based on availability if registering after July 17, 2026.

    Race is Rain or Shine

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    5kRunWalk via RunSignup
  • Distance: 10.1 km from Town of Lewisboro
    Sun, Aug 23, 2026 at 9:00 AM

    Peace, Love, Trails welcomes you to Raptor Ridge!

    Join us on Sunday, August 23rd at 9am!

    Run 6.5 miles of challenging trails in the Westmoreland Sanctuary

    The race starts and finishes at the Fox Lane H.S. Campus (at the back of the campus behind the Middle School gym).

    See if you have the intestinal fortitude to conquer RAPTOR RIDGE!

    Westmoreland Sanctuary is a not-for-profit, independent nature center and wildlife preserve located in Westchester County, New York. The land spans three towns: Bedford, Mount Kisco, and Armonk.

    We also need to thank the Fox Lane Sports Booster Club for all their help in allowing us to use the beautiful campus for our race headquarters and for the ever important parking!

    We will also be collecting food for the Mt. Kisco Food Pantry. If you would like to personally donate food, please bring non-perishable items that are within the expiration date.

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    6.5 MilesRunTrail via RunSignup
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