Plan a route here
Hiking trail

Hiking in the Berkshires: Dalton to Cheshire

Hiking trail · Massachusetts
Responsible for this content
Macs Adventure Verified partner  Explorers Choice 
  • /
    Photo: Chase Marston, Macs Adventure
  • /
    Photo: Chase Marston, Macs Adventure
m 800 700 600 500 400 300 200 12 10 8 6 4 2 km

A gentle section primarily through woodland connecting the small Berkshire towns of Dalton and Cheshire. 

13.9 km
4:00 h
342 m
397 m

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).

Author’s recommendation

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! User
Chase Marston
Updated: April 25, 2019

Highest point
680 m
Lowest point
294 m

Safety information


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: (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.

Tips, hints and links

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. 


Dalton AT Trailhead (370 m)
42.481759, -73.178485
18T 649712 4704875


Harbour House B&B Inn

Turn-by-turn directions

0.0 miles ­– From the parking lot, continue along the trail that begins behind the “Appalachian Trail Message Center,” which contains maps and useful information for the trail & area. 


0.15 miles – Stay STRAIGHT ON the trail at the point where another trail comes in from the left.


2.90 miles – Continue STRAIGHT ON under the power lines.


3.05 miles – After a short rise, BEAR LEFT to stay on the Appalachian Trail, leaving the campsite trail to your right.


5.20 miles – continue STRAIGHT ON the trail across an intersection with a faint, old double-track path.


6.00 miles – TURN RIGHT to visit the Cobble View Point. The 100meter addition is well worth the view.


6.05 miles – As you return to the main trail from the viewpoint, TURN RIGHT to rejoin the Appalachian Trail North.


6.5 miles – TURN LEFT to stay on the Appalachian Trail North, do not go toward Notch Road Parking.


6.65 miles – Continue STRAIGHT ON at an intersection with a faint, old double-track path.


6.90 miles – TURN RIGHT once the trail intersects with the pavement. The rest of the walk will be on pavement.


7.20 miles – TURN LEFT onto East Main Street.


7.30 miles –Shortly after, TURN LEFT onto Main Street.


7.40 miles – Across from the Post Office, TURN RIGHT into School Street. Take a moment to review any information on the “Appalachian Trail Message Center,” which has local maps of the town. Continue STRAIGHT ON School Street.


7.75 miles – At the T-Intersection, TURN LEFT onto Richardson Street.


7.95 miles – At the T-Intersection, TURN RIGHT onto North State Street / MA 8. Note, this is a busy section of road so proceed with caution and walk on the left side of the road.


8.60 miles – Arrive at the Harbour House B&B Inn, TURN LEFT into the driveway.


all notes on protected areas

Arrival by train, car, foot or bike

Similar routes nearby

 These suggestions were created automatically.

Questions & answers

Pose the first question

You have a question concerning this content? Here is the right place to ask it.


Write your first review

Be the first to review and help others.

Photos of others

13.9 km
4:00 h
342 m
397 m


: h
Highest point
Lowest point
Show elevation profile Hide elevation profile
For changing the range of view, push the arrows together.