A gentle section primarily through woodland connecting the small Berkshire towns of Dalton and Cheshire.
Begin just outside the town of Dalton at the Appalachian Trailhead. Enjoy tranquil, rolling terrain over gentle Berkshire hills, past peaceful babbling steams, and alongside Gore Pond. Spend the majority of the day walking through classic New England woodlands full of color and wildlife. Toward then end, take in the rewarding vista from the Cobble Viewpoint over Cheshire town & Mount Greylock. Lastly, arrive at your classic New England B&B for the evening's stay.
Note, you will want to bring a picnic from Pittsfield as there are not lunch options on the trail. Either grab a to-go lunch from The Hotel On North, or visit the Marketplace on main street in Pittsfield for a lunch to go (opens at 8am on weekdays, 10am on weekends).
Bring a picnic as there will be no lunch options, and the Cobbles viewpoint & a few lovely points along the way lend themselves to picnics.
The final section of the walk is along a paved road - though still in beautiful setting, it will be less exciting that they day's walk. Be sure to soak up the beauty of the woods before getting to the pavement!
Though the trail is well marked with the iconic Appalachian Trail white blazes, it can be easy to temporarily lose the trail or begin following a false trail. Any false trail will quickly end, so simply retrace your steps to the trail and look for the white blaze.
There are a number of small steam crossings on most trails in the Berkshires. There will be a clear route across but know that it might involve balancing on rocks or make-shift bridges. If the rock appears wet, it may be slippery. Use caution, and either poles or a stick for extra balance if needed.
After or during rain, the trail can become muddy, slippery, and harder to locate. Be extra cautious on wet leaves, rocks and mud to maintain balance, and pay extra attention to the white blazes to stay on the trail. Furthermore, rain will cause the streams to flow higher, making the crossings slightly more challenging. Remember, a wet boot is better than falling in the steam and potentially hurting yourself. If there is not a clear safe dry route across, find a safe wet route.
Various hunting seasons will overlap with the hiking season, so always wear a bright color in the spring and fall. Familiarize yourself with which hunting season might occur during your trip on the following website: http://www.eregulations.com/massachusetts/huntingandfishing/summary-hunting-season-dates/ (OR)
As always, be sure to check the weather before departing for the hike – New England weather is notoriously fickle, so always be prepared with proper layers and rain gear.
Bring hiking boots that are both comfortable and worn.
Always bring rain gear as the New England weather can quickly change. Bring also an extra layer or two, plus a warm mid-layer.
Bring dry, extra socks as they can be helpful to prevent blisters.
Though poles are not necessary, they are recommended for balance in uneven terrain and over steams as well as assistance with climbing and descending the steep hills.
Basic medical supplied, including blister protection.
Points of Interest
The Cobbles Viewpoint - toward the end of the walk, there is a short out-and-back with stunning views of Cheshire town, Mount Greylock, and Cheshire Resevoir.
Diane's Twist - an iconic Ice Cream stand along the AT that is well worth a stopover! Note, check the summer hours the day before.
Food and Drink
There will be not opportunities to refill water or acquire food along this day’s route. Be sure to bring enough of both for the entire walk. This includes 1-2 liters or water, a full lunch, and enough snacks keep you fueled. We recommend bringing a water purification method in the event of an emergency. Call our office or contact your local outdoor store for options.
The Marketplace Café, Pittsfield will be a great option for getting a lunch to go. They open at 8am during the week and 10am on the weekend, and make great sandwiches to go.
Once in Cheshire, you can stop at Diane's Twist for Ice Cream, or at The Duncan Donuts off of Rt 8, just south of the AT crossing.