Bikepacking In New England, Detours and All

4 min read

With peak foliage setting in, Don, Karen, Tanya and I boarded a train at Grand Central and headed north in search of beautiful dirt roads, and New England scenery. With an initial forecast of temps in the low 30s, we were pleasantly surprised to get off the train just two hours north of the city to find abundant sunshine and bright fall colors.

About 25 miles into our ride, we stopped for provisions in the town just outside of Steep Rock. Loaded up with plenty of stuffed clams, sausages and Lawson’s Sip of Sunshine beer to last us the night, we headed up over the last ridge of the day and dropped into Steep Rock Preserve– an 1000 acre land trust boasting miles of multi-use trails, a small number of remote camp sites and an abandoned railway tunnel.

After exploring the trails around camp, it was time to settle in for the night and focus thoughts on dinner. As I started the fire, Don and Tanya went to get the beers that were left to chill in the river. Our leisurely dinner took us well into the evening, as we helped ourselves to fire-roasted meats and veggies and chatted about the day’s ride.

On Sunday morning, we set out on foot for a half-mile trek up to Steep Rock summit, the tallest point in the park with views of “the clamshell”, a natural land formation caused by a dramatic change in direction of the Shepaug River. Our first (and thankfully only) encounter of the morning, a trail runner whose only passing remark of “watch out for the bear! He’s around” turned our conversation about breakfast to those rustles we heard collectively the night before. Eeeek! Upon reaching the summit, we were all left speechless by the stunning view afforded by such a brief hike.

After packing up and hitting the road, our return route was soon diverted by an out-of-control brush fire off Judd’s Bridge Road. Without fail, the Wahoo ELEMNT‘s preloaded maps gave us a clear detour to continue the ride. Despite the detour, the roads did not disappoint. We made our way to the American Pie Company in Sherman, CT–a cozy, local favorite. Sufficiently stuffed with lunch and pie, we rode over the last big ridge of the day. Over rolling hills through farmland and country roads we made our way east back to the train station. On board, we cheers-ed to a great weekend and future adventures.

These less-traveled and scenic roads are accessible with a short train ride from NYC.

Words: Seth Holmes

Photography: Donalrey Nieva

Ride completed by the 5th Floor club members.

Want more? Connect with us on Strava.

Leave a Reply

Your email address will not be published. Required fields are marked *