Mount Greylock, Berkshire County, Massachusetts
From the blustery 3,849-foot top of Greylock, the highest point in Massachusetts, you can see five states sprawling below you and feel like you’re the king of the mountain. You’ll also feel like you fought your way to that crown. It’s a long climb, especially if you start in North Adams and take Notch Road. The alternative is taking a longer ascent on Rockwell Road, which starts out in a tunnel of trees that gradually thins to show more sky as you get closer to the top and navigate some switchbacks and tight curves. Either way, you’re in it for the descent — you’ll have to take those tights turns fast but the average 6 percent will help you regain speed if you happen to touch the brakes. The roads are narrow, so watch for cars and other riders. And remember to lift your eyes to the view occasionally: At the top, you’re above the trees.