About the Ride & Retreat

Ride for a great cause! Join us for a fully-supported ride and community experience over Labor Day Weekend. People of all cycling levels and ages are welcome. Enjoy delicious, kosher, farm-to-table food, an inspiring Shabbat, engaging educational workshops, fun outdoor activities, and two days of cycling around the beautiful Berkshires.

Ride Details

On the Road

Cycle anywhere from 35 to 160 miles over two days. We offer multiple route options each day to keep it fun and challenging for riders of all levels. Ride past sparkling lakes, through quaint towns, over rollings hills, along green pastures, and on rail trails. This Ride is fully supported; routes will be marked, cue sheets will be provided, mechanics and medics will be available, and each route will have sweep vehicles.

We plan rest stops every 15-20 miles along all routes. Each rest stop has a variety of snacks, typically including energy bars, granola, potato chips, and fruit, as well as water and energy drinks. We strive to provide organic and healthy snacks while recognizing the need for high-energy food for cycling. Each rest stop has shade and restrooms. One or two rest stops serve as a lunch stop, which also includes sandwiches and other food. All food and snacks served on the Ride are kosher.

Both Sunday and Monday routes are loops starting and ending at Isabella Freedman. Enjoy great food, drinks, music, and more at our incredible celebratory finish!


Family Ride

We will be doing a Family Ride for children ages 5-11 on Sunday (September 1) of the Ride. This will be on a rail trail, with options to ride anywhere from 0-14 miles. Children are not required to fundraise. For more info, email ride@hazon.org.



  • All kids must be accompanied by an adult (parents can sign a waiver designating a non-riding adult if both parents want to ride)
  • The adult must have a car and is responsible for driving to the starting location and back to Isabella Freedman post-ride
  • Must provide your own bike (or scooter, or balance bike, or tricycle)
  • No riding without a helmet!
  • At least one adult in the family is required to fundraise
The Ride is a platform for my children to see a diverse and engaged community of leaders who share a common interest in making the world a better place and who are willing to put themselves out there and push boundaries in that pursuit.

The Route

Both days of riding provide various route levels, all of which are loops which return to Isabella Freedman. Each route will be fully supported and have its own highlights. There are decision points throughout the day where you can decide how long you want to ride. Each route option is described below the maps. View an interactive map, with the individual routes in detail.

Routes below are from 2018.

Sunday Routes

For the first day of riding, we are offering four routes – 35, 52, 70, and 100 miles – and each route will be fully supported and have its own highlights. There are decision points throughout the day where you can decide how long you want to ride.

Sunday 35-Mile Route

The 35-mile route (yellow) will split off from the other three at mile 3 and rejoin them at the Amenia Synagogue Rest Stop. This route will slowly gain elevation over the course of the first 10 miles, leading up to a large descent into the first and only rest stop of the day. After the first Rest Stop, all four routes will head north along a 7-mile rail trail, stop in the town of Millerton, and then split off once more to head straight back to Isabella Freedman.

Sunday 52, 70, & 100-Mile Routes

The 52-mile (green), 70-mile (blue) and 100-mile (red) routes will make their way southwest through Sharon, CT before crossing the border into New York State. The first Rest Stop is at the World Peace Center, after which all three routes will continue southwest and to the southern tip of route in Dover Plains. They will then continue back north to the second Rest Stop at the Beth David Synagogue where they’ll meet back up with the 35-mile route. Riders then cycle on the Harlem Valley Rail Trail for 7 miles between the Amenia Rest Stop and Millerton, NY.

At mile 45, the 52-mile route will split off and head back to Isabella Freedman, while the 70 & 100-mile routes will head north to the Massachusetts boarder. They will stop at their third Rest Stop at Bartholomew’s Cobble, after which the 70-mile route will head back south to camp and the 100-mile route will make one more loop north to Great Barrington and back.

Monday Routes

There will be three route options for the second day of riding – 30-miles (yellow), 45-miles (green), or 55-miles (blue).

Monday 30-Mile Route

All routes will begin the day riding southeast. The 30-mile route breaks off at mile 10 and will slowly gain elevation over the course of the first 10 miles, leading up to a large descent into the first and only rest stop of the day in Cornwall. Afterwards, the route heads back north along the river.

Monday 45 & 55-Mile Routes

The 45 & 55 mile routes make their way south towards the town of Litchfield. There are two rest stops on these routes. The first is at a camp in Goshen and the second is with all three routes at a park in Cornwall. The two routes are together most of the day, but after the first rest stop, faster riders can choose to head further south for a bonus 10 miles before rejoining the 45-mile route in Bantam.