A hiker descends towards Tumbledown Pond from the summit of Little Jackson. Ron Chase photos

A trek on Little Jackson and Tumbledown Mountains is the second-best mountain hike in Maine. How do I know its second best? I read it in my book, “Maine Al Fresco: The Fifty Finest Outdoor Adventures in Maine.”

Seriously, with the exception of Mount Katahdin, I can’t think of any mountain hike in Maine that exceeds Little Jackson and Tumbledown for majestic beauty. Several of the peaks in Acadia National Park certainly rival it. Bigelow and Saddleback Mountains are wonderful hikes. The Traveler Loop in Baxter State Park is truly exceptional. However, when I weigh the benefits of each, Little Jackson and Tumbledown is my choice.

Given my fondness for the dynamic mountain duo, I try to hike them each fall when the breathtaking autumn colors can be appreciated in a bug-free environment. Located in the mountains of western Maine, the mercurial pair is notorious for stormy fall weather. I’ve experienced gusty winds, frigid temperatures, ice pellets and snow during previous excursions.

Given my history with tumultuous weather on Little Jackson and Tumbledown, I watch for an outstanding forecast before planning a hike. I recently identified the perfect day with light winds and warm temperatures predicted, and absolutely no chance of frozen precipitation. When I announced a Penobscot Paddle & Chowder Society trip, my son Adam and longtime mountaineering friend Brent Elwell agreed to join me.

Climbers ascend a ridge on Little Jackson Mountain. Ron Chase photo

Accessing Little Jackson Trailhead is a chore. From the Byron Notch Road in Weld, would-be hikers need to drive the rough Morgan Road for about a mile to an area where there is limited parking. Shortly after leaving the trailhead, Tumbledown Mountain’s Parker Ridge Trail departs on the left.

The weather was exceptionally warm, sunny and calm when the three of us met at the trailhead early in the morning. Since my companions were much younger than me, I asserted my senior citizen prerogative and set the hiking pace.


We began in a predominantly hardwood forest and immediately encountered a minor disappointment; most of the leaves had fallen and cluttered the trail. Fortunately, some colorful foliage remained. Crunching through leaves, we soon passed the junction for Parker Ridge Trail — our anticipated return route.

After hiking steadily up for a couple of miles, we entered a conifer forest shortly after passing Pond Link Trail, which connects with Tumbledown Pond. The path steepened before we emerged above tree line at a junction between Jackson and Little Jackson Mountains. Little Jackson and Tumbledown on our minds, we decided to forego the less scenic but taller Jackson Mountain. From there, we enjoyed glorious views for much of the remainder of the day.

After proceeding over two steep, exposed escarpments, we climbed steadily up an elongated, sloping ridge towards the top of Little Jackson while savoring a panoramic vista of Webb Lake and Mount Blue in the east. A refreshing southwest breeze greeted us at the barren summit.

A short distance beyond the summit cairn, we encountered one of Maine’s most extraordinary views. Appearing directly below us was picturesque Tumbledown Pond surrounded by the three alpine peaks of Tumbledown Mountain.

We descended on an unmarked path that weaves precipitously down towards the mountain tarn. Nearing the pond, we turned right and soon began climbing steeply up huge, rounded boulders to the summit of North Peak, at 3,090 feet, the highpoint on Tumbledown. From the top, several trekkers were spotted on East Peak; the first hikers we’d seen.

Our intent was to traverse a densely wooded col to West Peak. Lacking an obvious route, we accidentally bushwhacked to East Peak. Next time, we’ll substitute a compass bearing for overconfidence.


Distinctive East Peak is similar to North in character. After scrambling up several steep ledges to the impressive summit, we descended gigantic granite slabs towards Tumbledown Pond, another marvelous Maine view.

Unlike most of our trek, the shore of the pond was bustling with activity. After exchanging trail information with other hikers, we ascended prominent Parker Ridge, where the last of the magnificent views were embraced.

Dropping steeply down, sore knees announced the consequence of the fourth significant descent of the day. The gentler gradient on lower Parker Ridge Trail was a welcome relief for tired muscles and aching joints while luxuriating in the satisfaction of having completed the second best mountain hike in Maine.

Ron Chase resides in Topsham. His latest book, “Maine Al Fresco: The Fifty Finest Outdoor Adventures in Maine” is available at northcountrypress.com/maine-al-fresco or in bookstores and through online retailers. His previous books are “The Great Mars Hill Bank Robbery” and “Mountains for Mortals – New England.” Visit his website at ronchaseoutdoors.com or he can be reached at [email protected]

Huge boulders are negotiated on Tumbledown Mountain’s North Peak.

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