7 Must-Do Peakbag Hikes in Western Maine

Updated: Nov 9, 2018

Tumbledown Mountain and Little Jackson

This is my favorite hike in Maine (aside from the Precipice Trail in Acadia). It didn’t hurt that the first time I hiked it was high fall foliage, the scenery was just absolutely stunning and the weather was perfect. Beginning at the Loop trailhead, the climb begins climbing gradually through forest and gets more challenging once hikers reach a bald ridge that looks straight up at Tumbledown. That’s when the real fun begins. The trail becomes moderately difficult due to its steepness and rock scrambling and more challenging in a specific spot called Fat Man’s Misery, a place that requires hiking straight up through a boulder formation that is a bit of a squeeze, with an iron rungs for assistance. Super fun! I have only ascended this way and I would generally recommend hiking up the Loop trail since I think it’s more fun going up the rock scrambles than going down.

Once the peak is reached, looking down from the 3,054 foot mountain the views are breathtaking; autumn colors and nearby Webb Lake to the Southeast, Mt Blue to the east and the mountains of Grafton Notch to the west. Following the Tumbledown Ridge back to the east, hikers can go through to Tumbledown Pond, another gorgeous spot to chill out for some relaxation. This is also an area where camping is allowed. From here hikers can choose to hike back down the Brook Trail to the road or continue on to Little Jackson mountain (3,470 feet) via the Pond Link Trail and Little Jackson Mountain Trail. The trail here and up on the summit are prime blueberry picking areas and one can spend significant time harvesting in late July and August.

The network of trails in the Public Lands run 10.6 miles. Going up the Loop Trail, summiting, continuing to Tumbledown Pond and down the Brook Trail is 4.3 miles round trip, plus about a half mile of road walking in between the Brook Trailhead and the Loop Trailhead. Beginning at the Little Jackson Trail, summiting and then heading down to Tumbledown Pond and down Parker Ridge Trail is 6.9 miles round-trip. The Parker Ridge Trail has a particularly wonderful view of the Pond and summits. Hiking up Tumbledown and Little Jackson together is 9.3 miles round-trip, plus about a half mile of road walking in between trails. I did each summit on two separate occasions and was pleased with each outing. Being so close to the area, I will be making regular trips to hike the trails again and camp.

Icy Tumbledown Pond in early November


Old Speck and the Eyebrow Loop

Old Speck Mountain is no hidden gem of Maine. Many have climbed and plan to climb the 4,180 foot mountain (the fourth highest in the state behind Katahdin’s two peaks, Sugarloaf and Crocker mountains). Grafton Notch State Park is a popular destination for a reason. It is a beautiful day trip and the trails connect to the Appalachian Trail making for a great opportunity for longer backpacking trips. On my first visit to the park, I hiked just the Eyebrow Loop and at 2.2 miles roundtrip it is an advanced, steep hike. There are sections of the trail that require the use of iron rungs along cliff rock faces. You can look up at this cliff face from the trailhead parking lot. The crux of the hike leads to a rock table, perfect for taking a break and having a snack. From here, hikers get magnificent views of the notch, Old Speck and mountains to the west. On the descent, a short section of the AT, hikers follow a trickling brook with cascades.

My second outing, I set my sights on climbing the 4,000 footer via the Eyebrow Loop and the AT heading west. After the Eyebrow Loop (described above), the trail climbs gradually and steeper at times through forest until the summit is reached. Panoramic views can be enjoyed from the observation tower. Heading back down the AT, hikers can choose to do a complete out and back or descend via the Eyebrow Loop trail. Heading down the Eyebrow proves a heady challenge due to its steepness and cliff scrambling. This will bring the hike to 7.6 miles roundtrip. Western Maine and onward toward Katahdin is known for having some of the roughest and toughest stretches of trail along the Appalachian. For more about sections of the AT I’ve experienced, see below.

Grafton Notch in summer


Sugarloaf Mountain

Up in the “skiing” region of Maine, the third highest peak in the state is one of the more popular hikes along the Appalachian Trail. Three different trailheads can take one up to the summit. On my adventure, I decided to hike in from the Western trailhead off of Caribou Pond Road; a very rough, unmarked dirt road (a high clearance or all wheel drive vehicle is helpful; mine was a tentative drive with teeth gritted), leading to the entrance to the AT junction of the Crocker Cirque and Sugarloaf. Other trails to the summit of Sugarloaf include the Fire Warden’s Trail, taking hikers up Mt. Abraham and Spaulding before summiting Sugarloaf (a grueling backpacking trek for another time) and Sugarloaf Trail, which takes hikers up the ski hill. Along Caribou Pond Road, there is a small parking area for a few vehicles and is approximately a half mile from the trailhead.

Choose your own adventure: turn left to Sugarloaf, turn right for the Crocker Cirque. On this day, I went left. Going right would come a few months later. The trail up to Sugarloaf is gradual to start and gets steeper and rockier during the climb. It’s a good slog and a great workout. Panoramic views await summiters and there is a large cairn on the top with the elevation painted on the side (4,249 ft.). Ski lifts sat immobile as I scampered around taking photos of the blue ridge mountains of Maine and stopping to eat my lunch (with flies and wind hampering it a bit, I decided to sit around the cairn for some protection). The out and back hike totaled 6 miles with some road walking. The wildflowers along the road on the walk back to my car were a lovely sight and I delighted in picking myself a small bouquet of some of my favorite local blooms: daisies, black eyed susans, and indian paintbrush.

Blue Ridge Mountains of Maine, as seen atop Sugarloaf


Caribou Mountain

Caribou Mountain lies within the Caribou-Speckled Mountain Wilderness in the White Mountains of Maine. The trailhead parking is off of Route 113 which leads into White Mountain National Forest. The hike up the Caribou Trail (make sure to start to the left as this is the best way to see the sights along the Morrison Brook) is a wooded, gradual climb and has some beautiful falls along the way, making for an enjoyable time before the summit, especially in the spring runoff season. Some of the most magnificent views of New Hampshire peaks I’ve experienced in this area can be found atop this peak. Every time I look back at the photos I’m reminded I had a perfect day for views. The loop back down makes for a fairly quick 5.7 miles round trip, good enough for a day hike and time to enjoy everything along the way.

White Mountains of Maine


Blueberry Mountain in White Mountain National Forest

Another wonderful hike in the White Mountains of Maine is Blueberry Mountain, which as the name suggests, is a great place for wild blueberry picking. The day I went was a bit early for harvesting, but nonetheless, a memorable experience. Just south of the Caribou Mountain trail, the trailhead parking for Blueberry is on Stone House Road off of Route 113, before the entrance to White Mountain National Forest. The hike begins along the dirt road before the actual trailhead, and leads up the summit, steeply at times (it’s only a 4.5 mile loop and sits at a 1,750 foot elevation).

In July, the greenery is spectacular and there are westerly views of the New Hampshire white mountains along the ridge. Once on the summit, hikers can meander along the granite rocks finding different spots to peak out at the neighboring mountains, and take a break of course. On the loop back down, a short side trail leads to Rattlesnake Pool, an aquamarine lagoon for a refreshing swim. It can get pretty crowded on hot days, as visitors can also choose to take a shorter route to get to just the pool and forfeit the summit. But the fun is in cooling off here after the hard work has been done! Loop back down to the road shortly after the pool area.

Hiker contemplation


Cranberry Peak

Of the hikes on this list, Cranberry Peak was the first one I climbed. This was also the hike where I realized that hiking was a super important part of my life if I was willing to get up at 5am, drive 125 miles in December for a day hike, and drive back home after. Cranberry Peak is part of the Bigelow Mountain Preserve in Northwestern Maine (only 28 miles south of the Canadian border) and it is one of the most difficult hikes I’ve done, mainly due to the icy December conditions. There are several trailheads to this peak; I chose the portion of the Appalachian Trail that intersects with the Range Trail and at 7.5 miles round trip and standing at 3,194 feet in elevation, it is no easy feat. The climb is steep and rocky and the trail is wooded until just before the peak. Cranberry Pond sits just after the intersection on the Range Trail. Views from the summit were foggy and cloudy, but still magnificent nonetheless. On a clear day, views of the Maine 4Kers are visible as is Canada. My short break on top consisted of taking a few quick snaps and getting out of the cold wind. I headed back down the same way I came up as the sun was setting, glad to be off of the ice before it got too dark.

Quick shot before the early winter wind blew me away


Saddleback Mountain and The Horn

This hike set a few firsts for me: my first Maine 4,000 footer, first double 4,000 footer, first ski slope hike, first 4,000 footer in the rain and fog and first 4,000 footer solo. Lying within the “ski region” of western Maine, Saddleback (4,120 feet) and The Horn (4,042 feet) are the 8th and 12th highest in the state, respectively. This was quite an adventure! The drive up was cloudy and a bit misty but the rain held off until I had made the summit. Lupine season was in full bloom and magnificent. Hiking up the ski slope was exposed and very steep; it worked different leg muscles because of the specific incline. I had to take breaks along the way, but the views began immediately. Rangeley Lakes are visible the entire way up.

The hill crests where the chairlift rests, but the true summit of Saddleback requires a bit more walking. This is where the ski hill intersects with the AT. The rain and fog grew more intense as I made the summit and prompted a pondering of whether I should continue to the Horn, the second summit. It wasn’t thundering and when I have a peakbagging goal it takes a lot to make me turn around, so I pushed on. Views within the saddle were nonexistent and I got some really great shots of the fog surrounding the mountains. Once on the summit of the Horn, the clouds cleared away briefly allowing me to peek through ever so slightly to nearby peaks and the lakes region. At 6.8 miles round trip for an out and back, it isn’t a huge hike distance wise, but it was a difficult climb due to the steepness and the conditions. There are two other approaches to the mountain, a section of the AT and the brand new Berry Picker’s Trail, which boasts wild blueberries and flowers along the trail and will be my next trip up to this mountain for sure

Saddleback through fog


There is always an adventure to be found in the mountains of Western Maine. The terrain, climate and weather are unpredictable and need to be accounted for on any given day, especially in high summer and winter. Maine hiking is unforgiving on knees and ankles, so be sure to take it steady and boost your joints with loosening exercises and stretches, before and after. Lace up those boots, grab a trekking pole or two, bring a lot of water, survival gear, and a camera and get ready to scramble!

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