Many people climb Tumbledown via Brook Trail. Mostly, the trail follows an old roadbed. It’s a nice, steady climb. The upper section follows a steep stream up a rocky slope to Tumbledown Pond. From there it’s 0.9 miles to the summit—most of it bare rock with wide open views. A great hike, but not Wicked Wild. (Although, the time I did it in a 50mph gale might count.)
On the other hand, the less-hiked Loop Trail climbs steadily then steeply for almost two miles to the summit. The trail climbs to Great Ledge with great views of the mountain and the route ahead. After dropping off the ledge, the trail steepens. You climb up into a narrowing chimney. The last half mile is very steep with loose rock. In spring, it’s like climbing a waterfall.
Near the top of the chimney is a boulder choke. The trail climbs through the boulders. There are iron rungs and some hand-and-knee crawling before you climb out the top of the choke.
At the top of the chimney, you turn left to climb the last 0.2 miles to Tumbledown’s open summit. You can turn right to hike 0.7 miles to Tumbledown Pond. You can make a nice 6.1 miles loop hike. (For more details, check out hike 34 in my guide Hiking Maine.)