4 events in Western Connecticut Planning Region, Connecticut

From big races to Saturday morning group runs—find 5k events and connect with the local endurance sports community.

• Tappen Brook 5K [facebook.com] [Register at ultrasignup.com]
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  Sun, Aug 09, 2026 at 9:00 AM

  5k

  221 Tappen Road, Western Connecticut Planning Region, Connecticut, 06752, United States
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• Hayfield Hustle and Oktoberfest at New Pond Farm [newpondfarm.org] [Register at runsignup.com]
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  Sat, Sep 26, 2026 at 9:30 AM

  Description

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  Ready, Set, RACE!

  Join us for the first annual New Pond Farm Hayfield Hustle! Choose from a scenic 5 mile, 5k, or Children's Sap fun run through the hayfields and byways of New Pond Farm, all...

  Ready, Set, RACE!

  Join us for the first annual New Pond Farm Hayfield Hustle! Choose from a scenic 5 mile, 5k, or Children's Sap fun run through the hayfields and byways of New Pond Farm, all finishing with a rollicking family-friendly Oktoberfest celebration. Races benefit New Pond Farm Education center, a nonprofit dairy farm of distinction and environmental education center. We educate and inspire each generation to become stewards of the land by championing conservation and sustainable farming practices to protect and preserve our natural world.

  The 5 mile race features gentle hills along rolling pastures, with waterfall views as you pass the Mark Twain Library, and finishes with a dash through our dairy barn.

  The 5K begins through the picturesque farmland, includes some challenging hills along winding country roads, and finishes with a fast and easy downhill run through our dairy barn.

  The Children's Sap run highlights the stream, pond, and animals of New Pond Farm, and will be untimed.

  Participants are welcome at all paces, including walkers. Jogging strollers are only allowed on the 5k course.

  Race registration includes entry into our family friendly Oktoberfest, which includes live music, a scavenger hunt throughout the 102 acres of pasture and woodlands, games, hay rides, and of course frosty beer. Food will be available for purchase.

  1k 5k 5 Miles Fun Run Run Walk

  101 Marchant Rd, Western Connecticut Planning Region, Connecticut, 06896, United States
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• The Joyce Allen Great Turkey Escape [runsignup.com]
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  Thu, Nov 26, 2026 at 8:00 AM

  Description

  The Great Turkey Escape 5K road race and 3/4 mile kids run.

  We will spoil our runners with a long sleeve tech shirt, an embroidered winter beanie (hat), embroidered running gloves and a finisher's medal along with 3 deep 5 year age group awards. The race begins and ends at the Redding Community Center on Lonetown Rd (RT 107) and all proceeds will be donated to our beneficiaries.

  1 Miles 5k Run

  Western Connecticut Planning Region, Connecticut, 06896, United States
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