IMO nowadays I feel like East Setauket is hardest trail on the island. It’s total mileage is around 22 miles for all 3 parts and has over 2500 ft of climbing. It also contains some of the hardest climbs around. All the newer cuts have really added variety and difficulty to the trail. I really like how sections ride very differenty. To ride East Setauket well, you need a mix of endurance, tempo control, bike control and good braking. It offers some of the few double black diamonds on the island. Except for Rocky Point and Shoreham only trails that have equal length or more. Although Shoreham isn’t a clean loop exactly, more of a jumble of trails…With a nice mix of fast downhills, technical switchbacks, and some rocky and rooty sections it keeps you focused and entertained. Definitely a great workout too!!
Lets see some images of the good parts, that will help me visualize.
For me Stillwell woods was the hardest ( at the time I have not been there in 5 years ) . I would ride multiple laps it was brutal.
It can be a tough trail if you hit it hard.
Stillwell has always been a difficult trail. It pushes your cardio with its short bursts of power with minimal recovery time. Technically it is challenging. Plenty of fast sections with switchbacks.