The “Trail”

I couldn’t hear Magoo behind me so I stopped. It was the last weekend of winter and we were attempting to complete our Winter Pinnacle Pursuit Challenge in the middle of Maine’s 100 mile wilderness on Whitecap Mountain.

We were about four hours into our climb. It had been about an hour since we had seen a blaze or any sign of the trail for that matter. It had been 30 minutes since we had not been forcing our way through thick branches. The GPS track we had taken during our Ultra Pinnacle Pursuit Challenge in August said we were on the trail, but with over seven feet of snow pack, the blazes were buried and we were bushwhacking whether we were on the trail or not.

The Road/Rink to Whitecap

We had driven in on a completely ice covered road. It was a white knuckle drive. We were not certain if we could get back out. We didn’t expect anyone would be traveling on that road in the near future. There was no cell service on the road. If we got stuck, we were on our own.

While we were prepared to survive out overnight if needed, survival is never a pleasant option — especially with an appointment the next day. Our youngest son was scheduled to have his wisdom teeth out, so we needed to be back in time to take him to that appointment. He was a little apprehensive about the procedure, but today, he was on his own.

Our oldest son was on his way back to college after spring break. When adding the time it took to drop off his girlfriend at her college, he’d be driving for about seven hours. When he had driven home for Thanksgiving, his car had broken down. We had been home to help out then. This time, he was on his own.

One of the pleasures of hiking for me is how it can root you firmly in the present moment, in the “here and now.” All other life concerns slip away. That is often the case, but not on all hikes.

Where’s Waldo?

Soon my thoughts of “there and then” where interrupted by the sound of branches brushing against Magoo’s pack. It still took another few minutes before I could see her through the thick high elevation stunted trees. “What do you think?” I asked.

“We’ve got to be getting close to tree line, right?”

“I don’t know, I think so. Should we cut our loses or push on?”


The Various Challenges

The Moosehead Pinnacle Pursuit Challenge is a collection of four different challenges involving six mountains in Maine’s Moosehead Lake region. The mountains are: Borestone Mountain, Big Moose Mountain, Eagle Rock, Number Four Mountain, Mount Kineo, and Whitecap Mountain.

The first, and easiest challenge is the Pinnacle Pursuit Challenge. This simply involves summiting all six mountains over any duration. As of March 16th, 2019 150 hikers had completed this challenge.

The second challenge is the Ultra Pinnacle Pursuit Challenge. To complete this challenge, hikers start and end from the Gazebo at the Moosehead Marine Museum and must climb all six mountains within a continuous 48 hour period. As of March 16th 27 hikers had completed this challenge.

The third challenge is the Winter Pinnacle Pursuit Challenge. To complete this challenge, hikers must complete all six mountains between January 1 and April 15 in the same year. Yes, it is still winter in the Moosehead Lake region until mid-April. Everybody else, enjoy your early spring. As of March 16th only four hikers had completed this challenge.

The fourth challenge is the Winter Ultra Pinnacle Pursuit Challenge. To complete this challenge, one must start and end from the Gazebo at the Moosehead Marine Museum and climb all six mountains within a continuous 48 hour period between January 1 and April 15. I suspect you would also need to have just the right snow and weather conditions, and pray someone has already broken all the trails for you. No one has reported to completing this challenge. I am uncertain if it has even been attempted.

Over the summer of 2017 Magoo and I completed the Pinnacle Pursuit Challenge. We weren’t blogging yet, so there are no post about this. On the Pinnacle Pursuit register we are listed as numbers 114 and 115.

In August of 2018 Magoo and I completed the Ultra Pinnacle Pursuit Challenge. On the Pinnacle Pursuit register we are listed as numbers 137 and 138.

During the winter of 2019 Magoo and I attempted to complete the Winter Pinnacle Pursuit Challenge.

The Tangible Challenges

Each version of the Pinnacle Pursuit has its own particular set of challenges. The logistics of just how to get to the trailhead is a significant obstacle of the winter versions. In 2019, only the Borestone Mountain trailhead was accessible by a plowed road.

Crossing Moosehead Lake

There is no road access to the Mount Kineo trailhead. In the winter you must cross the frozen Moosehead Lake. The crossing is one mile each way, and exposed to the winds which get funneled through this narrow passage of Maine’s largest lake.

Many years the road is plowed to the trailhead of Big Moose Mountain — not in 2019. This added three miles to the hike. We used skis on this unplowed road access and switched to snowshoes at the traihead. We also required a ride to be dropped off and picked up at the unplowed road since there was no place to park. Coordinating the pick up was complicated by the fact that there is no cell service at the pick up point.

The Approach to Big Moose

The Approach to Number Four

Access to the Number Four Mountain trailhead is on unplowed roads which adds five miles to the hike. We snowshoed in on this road, skis would have been a better choice. Another complication is that again, there is no parking available at the start of the unplowed road. So that will add even more distance to the hike, potentially several miles. In a lucky series of coincidences, we were able to get permission from a nearby camp owner to park at their camp.

Snowmobiling to the Eagle Rock Trailhead

There are several options for how to reach Eagle Rock, none of them short. The shortest approach we found, just to get to the trailhead, added ten, mostly unbroken, miles to the hike. This was the only hike that we used a snowmobile to reach the trailhead.

The access to Whitecap involves a long drive down dirt roads. The day we went, chains were required for the final five miles. Still, this only gets you to within four miles of the trailhead. We had studied maps and plotted a bushwhack that would shorten both the road hike and the overall climb. We used skis for the road portion and snowshoes on the trail.

Chaining Up

This is what the road access looked like in 2019. Other years will likely be different. Logistics, scouting, and talking to people in the area were critical for us to be able to attempt this challenge in winter.

Weather is, of course, another obstacle. It’s Maine. It’s winter. It’s cold, and the daylight is brief. On our hikes, the temperatures ranged from -5° F to 30° F without windchill. We experienced winds up to 30 mph.

Typical Trail Above 2500′ this Winter

The sheer depth of the snow this year also presented problems. Record snowfall totals were recorded in the Maine mountains this winter. Frequently the Moosehead Lake region reported having the deepest snow pack in the state. We climbed Borestone in early January. It was early enough that there were only a few inches of snow. For a majority of our hikes we were on multiple feet of snow. The area where the tree branches have been cut back to form the trail were often completely under the snow. When this happened we were bushwhacking even if we were on the trail.

Blazes Start to Get Buried Around 2000′

Route finding is also an issue in deep snow. On both Eagle Rock and Whitecap, the trail fluctuated between difficult to impossible to find. Trails that are obvious in the summer, become obscured by snow. We were glad we had taken GPS tracks during the summer to help — that, and over the years I have been honing my skills as a trail-whisperer.

Postholing Even with Snowshoes

Snow type was a major obstacle this particular winter. Most winters Maine experiences thaw and freeze cycles which help to consolidate the snow. For much of this winter in the Moosehead region it stayed cold, so the snow stayed powdery. Climbing Eagle Rock, we were often sinking in the snow over our knees — this was while wearing snowshoes. Our climbs up Big Moose and Number Four were in similar conditions.

There were challenges and struggles. Occasionally, we found ourselves in just a little over our heads. Other times, when anxiety threatened to emerge, we thought we were in way over our heads.

The Challenges Within

When Magoo asked if we were close to tree line, I suspected we were. The trees looked like we were. The GPS suggested we were. However, we were also very close to our pre-arranged turn-around time.

We pushed ahead.

Finally Above Tree line

In about ten minutes, we could see tree line on the other side of the thickest tangle of trees we had yet encountered. Once through, travel would be easier, not safer — perhaps less safe, but at least easier. Winds were 25—30 mph and the temperature was in the low twenties which put the windchill in the single digits.

Once through the final trees and above tree line we had cell service, so we called home to our son to let him know we were going to attempt the final push to the summit. In 30 minutes at 12:30 on March 17th, 2019, we had reached the summit of Whitecap to become the fifth and sixth people to complete the Moosehead Winter Pinnacle Pursuit.




The Call

While descending, but still above tree line, my cell phone rang. I’m not much of a phone person. My phone ringing is a bit unusual, and on this day, a little unsettling. It was my oldest son. He and his girlfriend were pulled over on the side of I-95. His car had made a loud bang and antifreeze was pouring out onto the road. After his last breakdown, we had purchased AAA for him. He is a mature and responsible young man, and we were confident in his ability to work his way through this on his own. It would present some struggles and challenges for him, but ultimately, it is under these conditions in which we grow and better ourselves.

While we felt a little parental guilt for not being there to help, his ordeal was really a reflection of what we were doing ourselves. As a couple who will soon qualify for the century class in partner events, we are still seeking that struggle and challenge in order to get closer to our better selves. Through the Winter Pinnacle Pursuit we had pushed our limits, made mistakes, had success, gone a little too far at times, but through this, we had learned and we had grown. Ultimately, this may be what we are chasing through these mountains, chasing, but only rarely catching — a slightly better version of ourselves.


Trip Data

All miles are for round trip.

Mountain: Borestone

Borestone: Not for Those Afraid of Heights

Elevation: 1923’
Date: 01/05/19
Start Time: 8:18 am
Summit Time: 10:30 am
End Time: 12:49 pm
Trip Duration: 4h 31m
Approach Miles: 0
Trail Miles: 3.7
Total Miles: 3.7
Gear: Snowshoes, Light traction
Fellowship: Brett, Rob, Nate, Nate
Blog Link


Mountain: Kineo

Fridged Summit of Kineo

Elevation: 1450’
Date: 01/19/19
Start Time: 8:57 am
Summit Time: 10:30 am
End Time: 12:04 pm
Trip Duration: 3h 07m
Approach Miles: 2.0
Trail Miles: 2.5
Total Miles: 4.5
Gear: Light traction
Fellowship: Brett
Blog Link

Mountain: Number Four

Elevation: 2890’
Date: 02/02/19
Start Time: 8:51 am
Summit Time: 12:15 pm
End Time: 2:16 pm
Trip Duration: 5h 25m
Approach Miles: 4.8
Trail Miles: 3.6
Total Miles: 8.4
Gear: Snowshoes
Fellowship: Brett, Christine, Jana, Sophie, Kattie, Marie
Blog Link
Trail Report Link


Mountain: Eagle Rock

Elevation: 2290’
Date: 02/18/19
Start Time: 8:39 am
Summit Time: 11:30 am
End Time: 1:16 pm
Trip Duration: 4h 37m
Approach Miles: Covered on snowmobile.
Trail Miles: 3.0
Total Miles: 3.0
Gear: Snowshoes
Fellowship: Just the two of us. We can make it if we try!
Blog Link
Trail Report Link


Mountain: Big Moose

Elevation: 3196’
Date: 02/23/19
Start Time: 7:52 am
Summit Time: 12:30 pm
End Time: 3:12 pm
Trip Duration: 7h 20m
Approach Miles: 2.9
Trail Miles: 4.4
Total Miles: 7.3
Gear: Snowshoes, Skis
Fellowship: Just the two of us. You and I!
Blog Link
Trail Report Link
Pack Link


Mountain: Whitecap

Elevation: 3644’
Date: 03/17/19
Start Time: 8:00 am
Summit Time: 12:30 pm
End Time: 4:30 pm
Trip Duration: 8h 30m
Approach Miles: 7
Trail Miles: 5.8
Total Miles: 12.8
Gear: Snowshoes, Skis
Fellowship: Just the two of us. Building castles in the sky!
Blog Link
Trail Report Link
Pack Link


Thank You

A special thank you to all those we hiked with this winter. We enjoyed meeting each and every one of you. We look forward to future adventures together. Also a thank you to those who maintain and participate on the various websites which helped us to learn about current trail conditions: the Maine Hiking Facebook page, New England Trail Conditions, and Northeast Trail Conditions. An extra special thank you to Dan who provided so much information on access and trail conditions; and to Jenny for shuttling us to and from Big Moose. This winter hiking community is so wonderful! If anyone needs additional information about either a winter Pinnacle Pursuit or any of the individual hikes, please reach out to us.



From there to here, from here to there, funny things are everywhere!

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