3 running and walking events in Litchfield, Connecticut

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

• Litchfield Hills Road Race [lhrr.com] [Register at runsignup.com]
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  Sun, Jun 14, 2026 at 1:00 PM

  Description

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  The LHRR is Litchfield County's premier road race. This challenging course inspires runners from all over the U.S. and the World to participate.. While we boast about our famous elite runners, the...

  The LHRR is Litchfield County's premier road race. This challenging course inspires runners from all over the U.S. and the World to participate.. While we boast about our famous elite runners, the LHRR also welcomes runners of all skill levels. Come and experience the hometown feel of this 7 mile run through some of the most beautiful scenery in New England. Runners are encouraged by the crowds, awed by the field, entertained by live bands all along the way and challenged by Gallows Lane -- the hill rated number 7 in Runners World Top Ten Hills and also the stretch of the course that Bill Rodgers had to shift into 9th gear to handle.

  We also offer children's races. Visit our website, www.lhrr.com for more info or call 860-459-9908 on our Children's Races.

  Once you've experienced Road Race Weekend for yourself, you will be among the hundreds of runners and spectators that flock back to Litchfield every year for the second Sunday in June -- and all the other festivities surrounding the race. According to Runners World Magazine, Its the best little race you've never heard of!

  7 Miles Run

  Litchfield, Connecticut, 06759, United States
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• Hillacious Half Marathon [runsignup.com]
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  Sat, Nov 14, 2026 at 10:00 AM

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  Why We Run

  The Hillacious Half was created to honor our military — to thank them and ensure their sacrifices are never taken for granted. The course is intentionally tough, representing the effort...

  Why We Run

  The Hillacious Half was created to honor our military — to thank them and ensure their sacrifices are never taken for granted. The course is intentionally tough, representing the effort and endurance our service members face every day, often far from their families. This is a bare bones race with no prize money and no frills — just grit, sweat, and the satisfaction of finishing one of the toughest courses around.

  All proceeds after race expenses go into a fund to support local military personnel and families who need a helping hand. Funds are distributed directly through the Hillacious Half, never to large agencies. Both the first-place male and female finishers have their names engraved on perpetual trophies housed at the Morgan-Weir American Legion Post 27 in Litchfield.

  We run this race in honor of those who serve and have served — carrying their strength with us up every hill.

  Dog Tags

  For an additional cost, participants and supporters can honor a veteran or service member with a personalized dog tag:

  • Runners: Add a tag during registration for $10.

  • Supporters (non-runners): Order a tag for $20.

  • Each tag is engraved with your veteran’s name and any additional info that fits.

  • Order by Oct 28 to have your tag ready for race day.

  • By wearing a dog tag, you bring that person “with you” on the course. It may be the motivation you need to conquer the next hill — and you keep it as a lasting honorarium.

  Race Options

  Half Marathon (Solo)

  13.1 miles of no-nonsense toughness. No medals, no prize money — just sweat and pride.

  2-Person Relay

  Two legs (~6–7 miles each). Separate timing and awards.

  4-Mile Walk (Timed)

  Same course start, then loops back for ~4 miles. Starts after all runners (~10:05 A.M.). Includes all runner amenities — yes, a beer at the finish.

  Proceeds & Impact

  100% of proceeds after expenses are held in a local fund for military members and families needing a helping hand.

  Funds are distributed directly by Hillacious Half, not via agencies.

  Beyond financial aid, your food and coat donations support local pantries and shelters.

  4 Miles 6.5 Miles 13.1 Miles Half Marathon Run Walk

  Litchfield, Connecticut, 06759, United States
  OpenStreetMap Google Maps

Local Clubs & Organizations