8 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.
Northwest Hills Planning Region
8 events in Northwest Hills Planning Region-
Sat, Mar 14, 2026 at 8:30 AM
Roxbury 5k
3.1 Miles, Down and Up Hemlock
Active duty military/veterans and active first responders are encouraged to contact the race for a discount.
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Sat, Apr 25, 2026 at 11:00 AMSee full details
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
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Registration available online only until 10:45 am on race day
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Race check in from 9:00 am
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Free Kid's Fun Run 10:15am
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5K timed run and 2M untimed walk events start at 11:00 am
Entry Fees
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5K timed run Individual Entry - $25
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2M untimed walk Individual Entry $25
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Family Group Registration (up to 6 people) - $50
5K race map HERE
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Sun, May 03, 2026 at 10:00 AM
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
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Sun, May 17, 2026 at 9:00 AMSee full details
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
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Adults: $25 online (early registration) | $35 on race day
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Youth (14 & under): $10
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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
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Sun, May 31, 2026 at 9:30 AMSee full details
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)
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No Animals, Roller Blades or Bikes
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Free T-shirts if registered by Friday, May 15.
MEDALS for First place finisher in each category.
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Sat, Oct 10, 2026 at 9:00 AMSee full details
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
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7:30 AM Race Day Registration and Packet Pick Up
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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+.
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