Appalachian Trail: North Adams to Great Barrington Massachusetts
Date: July 14-21
Trip length: Four days of hiking along with three days of travel on a Greyhound Bus.
Conditions: 70-90 degrees during the day accompanied by slight breezes and plenty of shade. Rain storms during one day and two nights. Temperatures at night ranged from low 40s to mid 60s depending on elevation.
Distance: 63.6 miles.
Distance from Cincinnati: North Adams is an eleven and a half hour drive.
Directions: I71 N – I271 N – I90 E – NY 7 E – NY 2 E – Phelps Ave in North Adams Mass.
The trail head is on the left side of Phelps Ave. up the hill past the elementary school.
Water: Sources are plentiful along this stretch. I was able to fill up multiple times a day while only carrying one liter at a time. All sources must be filtered but water from town was often available. The AWOL AT Guide provides all specific locations for water sources.
Highlights: Mt. Greylock, The Cobbles, St. Mary of the Assumption Church Hostel, Upper Goose Pond Cabin, Great Barrington, Tom Levardi’s house in Dalton, and the North Bound Hikers.
Description: Lying in the heart of New England, the Massachusetts section of the Appalachian Trail is highly developed. Every day you cross multiple roads and walk through towns such as North Adams, Cheshire, and Dalton. Opportunities to hitch into towns just a few miles off trail are plentiful. The terrain varies from steep climbs to astonishingly flat.
Day One: (14.7 miles) Hiking this section south bound (SOBO) means your first day will spent climbing over Massachusetts highest peak, Mt. Greylock, which stands at 3,491 ft. The climb is about 6 miles to the peak from the trail head in North Adams. Over those 6 miles you ascend 2800 feet with the bulk of that elevation gain achieved in the first 
three miles. Once you summit the climb down leads you into the town of Cheshire. St. Mary of the Assumption church allows hikers to stay in two rooms at the rear of the building. AC is provided in the building as well as restrooms and water. The church accepts donations for the generous service they provide.
Day Two: (15.2 miles) Leaving Cheshire you face some pretty casual terrain. Although the elevation profile shows rolling hills and flat terrain, beware that the trail is full of rocks and roots to dodge as you plod along. The A.T. winds it’s ways straight through the town of Dalton where Tom Levardi lives. Tom has been allowing hikers to grab water and even camp at his house for years. 
Many hikers congregate at his house to relax and enjoy good conversation. Ask him about borrowing a bike so you can ride to Angelina’s Sub Shop for their Steak Bomb Overload. But watch out you might not want to move for the rest of the day if you eat the whole thing! If you can muster the energy though, Kay Wood shelter is three miles up hill outside of town. There are small stealth camp sites by the streams seven and a half miles south of Dalton.
Day Three: (14.7 miles) All the way to Upper Goose Pond Cabin the trail is incredibly flat. This is a very relaxed day that ends at one of the best shelters along the A.T. The Cabin is half of a mile off the trail but well worth the trek. The caretakers at Upper Goose serve pancakes and coffee for breakfast every morning. Canoes are also provided at the cabin to explore Upper Goose Pond which has a cool little island out in the middle of the pond. The cabin is a big attraction for hikers so if you choose to stay, the likelihood of you running into thru hikers is very high. The 
cabin provides another great place for conversation and a taste of thru hiking culture.
Day Four: (19.0 miles) Between Upper Goose Pond and MA 23 (the road you take to hitch into Great Barrington) the trail picks up in elevation gain. You climb over a few hills including Mt. Wilcox which has three shelter options. Views are sparse and the sounds of the woods will be your entertainment for the day. Apart from the beauty of the woods there isn’t much to see but Great Barrington is a fantastic town! Restaurants such as the Neighborhood Diner, Siam Square, and the Gypsy Joint are great places to have a meal while celebrating the end of your section. Great Barrington has shuttle services that can take you to The Cookie Lady on Washington Mtn Rd. From there The Cookie Lady can shuttle you back to North Adams to grab your car and head home. 
