Sat, Jun 20, 2026 at 9:00 AM
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.
Cycling Gran Fondo Gravel
Sat, Jun 27, 2026 at 8:30 AM
8.4 km from CopakeCycling Gravel Mountain Biking
Sun, Jun 28, 2026 at 10:30 AM
49.1 km from CopakeCycling Road
Sun, Jun 28, 2026 at 8:00 AM
Welcome to the Stissing Triathlon in Pine Plains, New York. 2 hours north of NYC and halfway between the Hudson River and the New York/Connecticut border. You will find plenty of rolling hills and
serene landscapes tucked into this historical small town.
Sprint Triathlon & AquaBike:
800 yard swim; 12.6 mile hilly bike, 3.3 mile fast run.
Relay Teams of 2 or 3 are welcome for the Triathlon event only. Paratriathletes are welcome.
THERE ARE NO CUT-OFF TIMES!
***Please see FAQ's regarding bringing dogs to the race.
13 Miles 16 Miles Aquabike Cycling Run Swim Triathlon
Sat, Jul 04, 2026 at 9:00 AM
The 5K race in Historic Saugerties, NY, is an exciting event that draws participants of all ages. Set against the backdrop of this charming town, the race offers a unique blend of scenic routes and community spirit. Fun, Family and Fitness in Upstate NY!
5k Run
Sat, Jul 11, 2026 at 8:00 AM
Unique and beautiful setting at Hopkins Vineyard in the picturesque Northwest corner of Connecticut. Swim and bike around celebrated Lake Waramaug. Space is limited so don't hesitate to secure your
spot in what has been described by participants as the "most elegant triathlon in the Northeast"!
Sorry, no refunds, transfers or deferments, for any reason.
Event details and schedule
Course and event info here:
http://hopkinsvineyardtri.com/course-description
Race Day packet pickup starts at 6am, race start is 8am.
Triathlon
Sat, Jul 11, 2026 at 7:30 AM
The challenging, highly rewarding Litchfield Hills Triathlon allows athletes to enjoy the scenic beauty of New Hartford, CT, and the surrounding area in this Olympic distance event.
Olympic Triathlon
& AquaBike
Start with a 1500m swim in the crystal clear waters of famous West Hill Lake, among the cleanest freshwater lakes in Connecticut, followed by a 40K bike course with stunning mountain vistas and finish with a 10K run on rural back roads.
Paratriathletes and relay teams are welcome.
THERE ARE NO CUT-OFF TIMES FOR THIS EVENT
25 Miles 31 Miles Aquabike Cycling Run Swim Triathlon
Sat, Jul 11, 2026 at 9:00 AM
Join us Saturday, 7/11/2026 for our Fifth Annual Smile Like Jack Family Fun Run/Walk. We will have food, beverages (21+ options too), amazing raffles, music, and lots of smiling faces!
Early check-in
will be held Friday 7/10/2026, from 4-7 PM at the Knox Trail Inn, for those who wish to get their bibs the evening before.
Day of registration and check-in begins promptly at 7:00 AM, while the race kickoff is at 9 AM.
Prices:
Competitive Race (Chipped Timed) 5k/10k
$40
Family Fun Run/Walk (Not Timed)
$35
We hope to see you there!
Cutoff for T-shirts will be June 1st. This event is rain or shine!
JACK'S STORY
The Smile Like Jack Memorial Fund was established in memory of Jack William O’Brien, a loving son and brother, caring friend, and hard working young man that touched the lives of many with his contagious smile. Jack tragically passed away in a snowmobile accident on March 3rd, 2022. In his 20 short years, he had accomplished many things and leaves behind a legacy that is in a caliber of its own. Jack lived life to the fullest. He was always working exceptionally hard to accomplish his set of goals while also living the outdoorsman lifestyle: fishing, hunting, and riding. Our goal is that the Smile Like Jack Memorial Fund will bring other individuals (with similar passions) the opportunity to live their legacy just as Jack would - working immensely hard in the trades and living life to the fullest in the great outdoors.
For additional information on The Smile Like Jack Memorial Fund, and for live updates, please visit our website: https://smilelikejack.com
3.1 Miles 5k 6.2 Miles 10k Fun Run Run Trail Walk
Sun, Jul 26, 2026
37.4 km from CopakeHalf Marathon Run
Sun, Jul 26, 2026 at 7:30 AM
Eastern Dutchess Road Runners Club
Junkyard Dogs Hilltopper Half
Date: Sunday, July 26th, 2026
Time: 7:30 AM (Sharp, Rain or Shine)
Packet Pick-Up: 6:30 AM
Time Limit: 5-hour cap
The net proceeds and
donations will support the Lustgarten Foundation for pancreatic cancer research. For more information, visit lustgarden.org.
Run Description:
Join us for an informal run through the charming town of Washington. The course is 13.1 miles of beautiful country roads, featuring scenic views of lakes, ponds, and expansive farmland. Please note that this run is not suitable for novice runners, as it includes many hills and an elevation gain of 787 feet. The roads will remain open, and self-service water stations will be available every few miles.
Registration:
$30 for Non-Members
$25 for Members
No Race Day Sign-Up
Race Caps at 50 participants
Discounted price are available for club members. Become a member at EDRRC.ORG
Awards:
Overall 1st, 2nd, and 3rd Male, Female and Non-Binary Runners.
A finisher medal is guaranteed to particpants who register before date TBD.
Location:
Millbrook School
296 Millbrook School Rd
Millbrook, NY
Parking:
Parking is available at Trevor Zoo, located at Millbrook School, 282 Millbrook School Rd, Millbrook, NY.
13.1 Miles Run
Sun, Aug 02, 2026 at 7:00 AM
49 km from CopakeCycling
Fri, Aug 07, 2026 at 9:00 AM
50 km from CopakeCycling Gravel Mountain Biking
Sat, Aug 08, 2026 at 7:00 AM
44.3 km from CopakeUltra
Sat, Aug 08, 2026 at 9:00 AM
49.1 km from CopakeCycling Gran Fondo
Sun, Aug 16, 2026 at 10:00 AM
Like Running or Walking? Love Wine? This race is for you!
Join us on Sunday, August 16, 2026 at 10:00am for an exciting annual event that features the amazing scenery and landscape of the Millbrook
Vineyards & Winery! This winery was called "the Hudson Valley's Flagship winery" by The New York Times! So come out and join us for this amazing event! Whether you are looking to run, walk or just enjoy the wine this race is a sure thing for a great time and an incredible experience! This race is timed and scored by J3 Timing. Results will be posted at www.J3Timing.com.
Registration Includes:
T-shirt: Super Soft Ring Spun Cotton t-shirt included!
Wine Glass: Shatterproof, Collapsible, and Portable!
Finisher Medal: Doubles as a Wine Stopper!
Race Bib: Chip timed 5k run/walk
Results Posted Online
...and of course, a pour of wine!
1.5 Miles 5k Run Walk
Sat, Aug 22, 2026 at 8:00 AM
9.6 km from CopakeUltra
Sat, Sep 12, 2026 at 8:30 AM
43.8 km from CopakeCycling
Sun, Sep 13, 2026
37.6 km from Copake12k 25k 50k Trail Ultra
Sun, Sep 13, 2026 at 10:00 AM
The Pro/Cat1/Cat2 course is just over 5 miles long, while the Cat3 course is 3 miles long. They start out on the same trail, but there is a short bypass for the Cat 3.
There is plenty of parking at
Rielbauer's, as well as flush toilets, an outdoor shower, and an outdoor Bier Garten serving Bratwurst and Beer! Riedlbauer's requests no coolers, as they earn their revenue from the Bier Garten.
Riedlbauer's also has rooms with meals included, but they will probably sell out, so book early if you would like to stay. There are plenty of lodging options nearby if they do sell out, some suggestions can be found on the Round Top Mtn. Bike Association's website at RTMBA.org.
Ride hard and have fun!
Cycling Mountain Biking Trail