4 running, walking, cycling, and other events in Litchfield, Connecticut
From big races to Saturday morning group runs—find running, walking, cycling, and gran fondo events and connect with the local endurance sports community.
Litchfield
4 events in Litchfield-
Sat, Feb 14, 2026 at 11:00 AMSee full details
24th Annual Bob & Peg Andrulis Sweetheart 5 mile Run & 3 mile walk will be held on Saturday, Feb 14 2026 with snow date Feb 21. All ages welcome. Runners and walkers enjoy a course that follows a beautiful route through whites woods along dirt and paved roads. Support on course and wonderful refreshments and age groups award ceremony held indoors at the Litchfield Community Center after the finish. Proceeds from the event benefit the Center's family and youth programming.
***Children 10 and under is $10
***80 years old and above is FREE
Timing by Fast Track Timing Systems
USATF CERTIFIED 5 MILE COURSE #CT13035JHP
**PRICE INCREASE ON 2/12 AT NOON TO $35
***PLEASE NOTE THERE IS RACE DAY REGISRATION STARTING AT 9:00 AM - 10:45 AM, COST IS $35!
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Sun, Jun 14, 2026 at 1:00 PMSee full details
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!
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Sat, Jun 20, 2026 at 9:00 AMSee full details
HedgeFondo
A premium cycling event rooted in the Litchfield Hills, designed with the care of a world-class riding experience.
Hedgefondo is a thoughtfully produced cycling event built to showcase the Litchfield Hills as one of the Northeast’s premier road and gravel riding destinations, with easy access from New York and Boston. What began as a small, private ride among investment bankers—hence the name Hedgefondo—quickly grew by word of mouth to more than 250 participants in its first public year, with over 500 riders expected this season from the New York, Connecticut, and Boston regions. Based at Rifugio, a premier active hospitality hub in the Litchfield Hills, the event pairs curated routes with elevated pre- and post-ride hospitality, creating a true basecamp for the day. Hedgefondo is coordinated and spearheaded by KC&E Adventures, a team with over a decade of experience designing premium cycling experiences around the world and featured in Forbes, Men’s Journal, Cycling Magazine, Yankee, and Bicycling.
Event Website
Route Options & Descriptions
Hedgefondo offers two route tiers—Adventure and Endurance—each available in road and gravel formats and supported by an on-course aid station.
Adventure Distance
Road: ~41 miles
A thoughtfully curated road route through the heart of the Litchfield Hills, featuring quiet country roads, rolling terrain, and classic New England scenery. Riders will pass lakes, historic stone walls, open farmland, and wooded corridors that define the region’s character, offering a rich and engaging ride from start to finish.
Gravel: ~30 miles
A mixed-surface route highlighting the Litchfield Hills’ network of quiet dirt and gravel roads. This ride weaves through rural landscapes, wooded backroads, and hidden corners of the region, including sections near White Memorial Preserve, showcasing the area’s natural beauty and sense of exploration.
Endurance Distance
Road: ~70 miles
An expansive road route designed to showcase the depth and variety of riding in the Litchfield Hills. The course links together rolling hills, longer climbs, and extended stretches of quiet pavement, passing lakes, farms, and stone-lined roads that reflect the region’s historic and pastoral landscape.
Gravel: ~53 miles
A full-distance gravel route that dives deep into the region’s most remote and scenic terrain. Riders will travel long stretches of dirt and gravel roads, forested corridors, and protected lands, including extended exploration around White Memorial Preserve, offering a rugged and immersive New England gravel experience.
Event Day Overview
7:00 a.m.
Event site opens. Registration, sponsor and partner areas, Rifugio operations, and parking are fully set.
7:30 a.m.
Registration opens.
9:00 a.m.
Endurance Routes depart (road and gravel).
10:00 a.m.
Adventure Routes depart (road and gravel).
12:00 – 4:00 p.m.
Post-Ride Gathering at Rifugio
Food and beverages, sponsor and partner activations, music, and space to unwind, connect, and kickoff summer.
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Sat, Nov 14, 2026 at 10:00 AMSee full details
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:
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Runners: Add a tag during registration for $10.
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Supporters (non-runners): Order a tag for $20.
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Each tag is engraved with your veteran’s name and any additional info that fits.
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Order by Oct 28 to have your tag ready for race day.
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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.
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Local Clubs & Organizations
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Club
USA Swimming Club. 15 members.
[email protected] +1 860-480-2017