Western Massachusetts has several notable mountains. The highest mountain in the state (Mt. Greylock) is there. More interestingly, Mt. Frissell, whose southern slope contains the highest point in Connecticut (Bear Mountain, the highest peak in CT, is about 50 feet lower) is in the Southwestern corner. There is another summit nearby that induces the exact same reaction from every single person. That mountain is Mt. Everett. [pause for audience pun] No, Mt. Everett.
The hike from Jug End Rd in Great Barrington to the peak of Mt. Everett is a moderate 9.2-mile round trip (it took us just under 6 hours). The beginning of the hike features some rock scrambling and some confusing switchbacks. Enough people have missed the switchbacks that the ground is worn in a trail-like manner going in the wrong direction. For the first mile or so, make sure to pay careful attention to the white blazes. You’ll get to the top of a ridge that would have had some great views if it wasn’t the hottest, humidest, haziest day of the year. At about the 4-mile mark, you arrive at Guilder Pond, a really fantastic swimming hole. If it’s a hot day, bring a pair of trunks and a towel and a water filter. You’ll be glad you did. (We didn’t.)
The top of Mt. Everett is actually pretty dull. The fire tower was torn down in 2003, and all that’s left is the foundation. By the time you get to the pond, you’ve already climbed most of the way up. The 360-degree view looks like it’s probably pretty great on clear days.
Note: I realized the other day that M and I do a whole lot of hiking. I want to start writing up some of them here 1) for posterity, 2) for future reference, and 3) so you and random Googlers can use our experience to plan hikes.