Day 200 of a northbound Appalachian Trail thru-hike turned into one of the most rewarding stretches of trail in Massachusetts, and it's a good window into why this section keeps drawing long-distance walkers.
The day started near Dalton with a rough night's sleep — coyotes howling and something light-footed crunching through leaves about 50 feet from the tent, close enough to rule out a bear but not close enough to ignore. A late start followed, though not before a memorable wildlife encounter just outside town: a porcupine that, instead of fleeing, calmly climbed a nearby tree. Many hikers never learn porcupines can climb at all, so watching one scale upward was the surprise of the morning.
Dalton itself is a classic trail-town stop. Hikers gathering on the porch of a Depot Street home belonging to a well-known local trail angel, who lets thru-hikers tent on his lawn — the front yard marked by a circle of trekking poles planted in a flower bed. The group there reported an overnight freeze, with tents frost-covered at dawn, a reminder of how quickly autumn conditions can shift in the Berkshires.
The main event was an afternoon push over Mount Greylock, Massachusetts' high point at 3,491 feet. After a slow morning, the hiker covered nine flat miles in three hours, then ground up the Greylock Range through steady climbs, reaching the summit just after 5:00PM. But instead of lingering on the cold, windy top, the plan was to race 3.7 more miles to the Mount Prospect overlook, which faces west — the right direction for a sunset at 6:23PM. That meant a steep, rocky descent off Greylock on stone steps and slab, then a sustained all-out effort with failing insoles folding underfoot. The payoff: reaching the overlook with 10 minutes to spare for a sunset over the Taconic Range, with Williamstown and the neat farms along Route 7 spread out below. Camp that night was at Wilbur Clearing shelter, cutting nearly four miles from the next day's itinerary.
For anyone eyeing this stretch, the practical takeaways are clear. The Dalton-to-Greylock section offers genuine trail-town hospitality, reliable water sources (though late-season streams can run slow and leaf-choked), and viewpoints that reward timing. The final mile up Greylock is steep, and the descent is hard on knees and footwear — gear that fits properly matters more than usual. Overnight frost is possible even when daytime hiking feels warm, so check sleeping layers accordingly.
Who is this for? Thru-hikers planning a northbound itinerary will find useful intel on pacing, camping spots and trail magic around Dalton. But it also works as inspiration for section hikers: a weekend loop over Greylock with a sunset at Mount Prospect is a realistic and spectacular goal, no 2,000-mile commitment required.
Story via The Trek.
