10 events in Northwest Hills Planning Region, Connecticut

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

• Shane Kinsella Memorial 5K Run or 2M Walk [runsignup.com]
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  Sat, Apr 25, 2026 at 11:00 AM

  Description

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  The annual run/walk is a memorial to Shane Kinsella who died from SIDs in 2008. Proceeds from the event go to the SMK Children's Fund available to Goshen children.

  T Shirt - given to the first 100...

  The annual run/walk is a memorial to Shane Kinsella who died from SIDs in 2008. Proceeds from the event go to the SMK Children's Fund available to Goshen children.

  T Shirt - given to the first 100 participants who register prior to March 27, 2026.

  Race Schedule

  • Registration available online only until 10:45 am on race day

  • Race check in from 9:00 am

  • Free Kid's Fun Run 10:15am

  • 5K timed run and 2M untimed walk events start at 11:00 am

  Entry Fees

  • 5K timed run Individual Entry - $25

  • 2M untimed walk Individual Entry $25

  • Family Group Registration (up to 6 people) - $50

  5K race map HERE

  2 Miles 5k Fun Run Run Walk

  291 Beach Street, Northwest Hills Planning Region, Connecticut, 06756, United States
  OpenStreetMap Google Maps
• Glenholme 5K Run For Autism [runsignup.com]
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  Sun, May 03, 2026 at 10:00 AM

  Description

  Join us for The Glenholme School 5K Run for Autism - one of the most scenic 5K runs in Connecticut! You won't find a more beautiful Course: scenic flat, fast, out-and-back course on a dirt road that winds along the Shepaug River. Dogs Welcome!

  REGISTRATION LINK TO BE PROVIDED SOON

  5k Run

  2 Tunnel Road, Northwest Hills Planning Region, Connecticut, 06794, United States
  OpenStreetMap Google Maps
• 2026 Rossiter Run 5K Race and Fun Run/Walk [runsignup.com]
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  Sun, May 17, 2026 at 9:00 AM

  Description

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  Are You Up for the 6th Annual Steep Rock’s 5K Challenge? You’re invited to Steep Rock Association’s 2026 Rossiter Run 5K Race and Fun Run/Walk on Sunday, May 17th at 9:00am in Steep Rock Preserve!...

  Are You Up for the 6th Annual Steep Rock’s 5K Challenge? You’re invited to Steep Rock Association’s 2026 Rossiter Run 5K Race and Fun Run/Walk on Sunday, May 17th at 9:00am in Steep Rock Preserve!

  The racecourse follows a scenic route along the Shepaug River with a gradual incline in the stunning Steep Rock Preserve.

  Join us for the challenge and the chance to celebrate your achievement at the finish line!

  Registration Fees

  • Adults: $25 online (early registration) | $35 on race day

  • Youth (14 & under): $10

  • Fun Run/Walk: $5

  Fun Run/Walk participants are untimed and will not receive a race bib.

  • Please note: All registration fees are non-refundable.

  Go Green: To show your love of the environment, please bring your own water bottles; we will have water to refill them.

  Awards

  Overall:

  🏆Prizes awarded to 1st place Male, Female, and Nonbinary finishers.

  Recognition - Age Groups:

  Top 3 Male, Female, and Nonbinary finishers in each of the following age groups will be recognized:

  19 & Under | 20–39 | 40–59 | 60+

  Overall winners excluded from age group recognition. Nonbinary awards will be presented when there are at least three registered participants in the category.

  ➡️View Course Map

  3.1 Miles 5k Fun Run Run Walk

  2 Tunnel Road, Northwest Hills Planning Region, Connecticut, 06794, United States
  OpenStreetMap Google Maps
• 17th Annual Barkhamsted River Run 5K [runsignup.com]
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  Sun, May 31, 2026 at 9:30 AM

  Description

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  Fundraiser for the Town of Barkhamsted elementary school. Please join us and support our kids.

  Course: Scenic, fairly level out and back course (two hills) along the Farmington River and People's...

  Fundraiser for the Town of Barkhamsted elementary school. Please join us and support our kids.

  Course: Scenic, fairly level out and back course (two hills) along the Farmington River and People's State Forest in the Northwest Hills of Litchfield County.

  Race Day Schedule: Registration will begin at 8 - 9:15 am, 5K Race Start 9:30 am & Kids 1M Fun Run & 10:30am. T-shirts will be provided for those registered by Friday, May 15th.

  Parking: Barkhamsted Elementary School (65 Ripley Hill Rd., Barkhamsted, CT 06063)

  • No Animals, Roller Blades or Bikes

  • Free T-shirts if registered by Friday, May 15.

  MEDALS for First place finisher in each category.

  1 Miles 5k Fun Run Run

  65 Ripley Hill Road, Northwest Hills Planning Region, Connecticut, 06063, United States
  OpenStreetMap Google Maps
• Hartland Harvest Run [o2eventproductions.com] [Register at runsignup.com]
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  Sat, Oct 10, 2026 at 9:00 AM

  Description

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  The Race starts and ends at the Bethany Lutheran Bretheran Church, whose members have once again generously offered us use their space for this event.

  Race Day

  • 7:30 AM Race Day Registration and...

  The Race starts and ends at the Bethany Lutheran Bretheran Church, whose members have once again generously offered us use their space for this event.

  Race Day

  • 7:30 AM Race Day Registration and Packet Pick Up

  • 9:00 AM 5K Run

  REGISTRATION

  PRE-REGISTRATION:

  Individuals: $25 until 7/31, $30 until 8/1, $35 on Race Day

  T-Shirts guaranteed if registered by September 24th, 2026 (Must be present to receive)

  Awards

  Top Male and Female Finishers

  The top three in the following age groups: 12 and under, 13-18, 19-29, 30-39, 40-49, 50-59, 60-69, 70-79, 80+.

  5k Run

  116 Walnut Hill Rd, Northwest Hills Planning Region, Connecticut, 06027, United States
  OpenStreetMap Google Maps
• Mohawk Mountain Race [steependurance.com] [Register at ultrasignup.com] - Facebook
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  Sun, Oct 11, 2026

  5k 10k Half Marathon

  46 Great Hollow Road, Northwest Hills Planning Region, Connecticut, 06796, United States
  OpenStreetMap Google Maps