Route Information

Sunday Routes

2017 Route Map - SundaySunday’s routes explore the Connecticut and Massachusetts Berkshire Mountains. We are offering four routes – 36, 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.

The 36-mile route (yellow) will split from the other three routes at mile 12. This route will have rest stops at two parks – Bartholomew’s Cobble, a forested park with a 15-mile loop trail to a bluff overlooking the Housatonic River, and Beckley Furnace, a 19th century iron blast furnace on the north bank of the Blackberry River.

The 52-mile route (blue) will explore more of the countryside, with picturesque roads alongside small creeks. This route will have the same first rest stop as the 70- and 100-mile routes at the Appalachian Trail Conservancy and a second rest stop where all routes come together at Beckley Furnace.

The 70-mile route (red) will split from the 52-mile route at mile 48 and continue the loop to the south. There will be an additional rest stop at a park in Cornwall, where riders can enjoy shade and picnic tables under a pavilion. It comes after a long steady climb into an incredible descent. From there, the route make its way back north along the river to Isabella Freedman.

The 100-mile century (green) will split from the 70-mile route at mile 54 and has a small dedicated rest stop at a camp in Goshen, CT. Afterwards, this route has a large loop even further south that wraps around Bantam Lake. It then heads back north to Cornwall to join the 70-mile route before heading back to Isabella Freedman. For those that need a break around the southern tip of the loop, there is an un-manned pit stop at a local ice cream shop.

Click here to view an interactive map, with the individual routes in detail

Monday Routes2017 Route Map – Monday

We have three route options on Day 2, two of which are loops to the southwest of Isabella Freedman, heading into New York State. The third heads back down south to Cornwall.

The 30-mile route (yellow) heads south towards the town of Cornwall, mimicking the second half of the 70-mile route from Day 1. 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. Afterwards, the route heads back north along the river.

The 50-mile (green) and 60-mile (blue) routes will make their way southwest through Sharon, CT before crossing the border into New York State. There are two rest stops on these routes. The first is at the World Peace Center and the second is at a temple in Amenia, NY. The routes are together most of the day, but after the first rest stop, faster riders can choose to head further south for a bonus 9 miles before rejoining the 50-mile route in Dover. Riders be on the Harlem Valley Rail Trail for 7 miles between the Amenia Rest Stop and Millerton, NY. After the trail ends, it is another 10 miles to return to Isabella Freedman for the celebratory BBQ lunch.

Click here to view an interactive map, with the individual routes in detail


The Hazon Ride was a profoundly moving experience for me. Riding over one hundred miles that weekend is one of my greatest accomplishments. At the end of my ride I broke out in spontaneous and unexpected tears.
—Falynn, 30s