On my own on the Osceolas with Captain Samuel Willard

On the Osceola Trail, I’m on my own, but hiking in footsteps more than 250 years old  — maybe.  As I hike uphill on a moderate-grade-by-White-Mountain-standards, I wonder if this slope is the same one that Captain Samuel Willard and his company of Indian hunters bushwhacked through when they climbed up “a very steep mountain” in the fall of 1725.

Osceola is a popular peak, but on this Monday in June, I have the summit to myself for a blessed few minutes. I take in the sweeping views of Mount Tripyramid, granite-covered Chocorua, and countless others. Waterville Valley’s dense green tree cover is broken in places by condo developments and patches of road, but the view is much the same as Willard described in his journal: “Being on top of ye hill cou’d Discover no where nigh us, anything but steep mountains.”

I eat my usual hummus sandwich and would love to stretch out on the summit ledge and hang out with the black flies. But if I do, I may lose motivation to climb East Osceola. All around me, hikers who have completed the three-mile hike to the summit are throwing in the towel on the one-mile trek to the east peak, which lacks views.

Willard and his company had no choice in the matter. Having pushed through the forest to reach these ledges, they had to continue. They had traveled many miles since leaving Dunstable, Massachusetts in early September. The men were Indian hunting, both to secure the frontier but also to collect bounties of 100 pounds for every Indian scalp they brought back.

Did Captain Willard and his command of 20 men look over the edge of this granite cliff back in 1725?

Did Captain Willard and his command of about 20 men look over the edge of this granite cliff back in 1725?

An 1724 Indian raid upon Dunstable, Massachusetts (which then covered a huge swath of territory, including much of southern New Hampshire, up to Nashua) served as the motivating event for this journey (albeit somewhat indirectly). The bigger picture, however, was the ongoing power struggles between Britain and France and the fallout for New England’s Native Americans.

In the aftermath of Queen Anne’s War, concluded by treaty in 1713, many questions continued to simmer about the official boundary between New France and British America.  The French-allied Abenaki (and other Wabanaki groups) disputed certain aspects of the treaty, as they had been excluded (predictably) from negotiations.  The Abenaki contended that they had never ceded their claims to lands in northern New England.

Discovering a few blooms of trillium on the rocky trail is one bonus of having to watch my footing.

Discovering a few blooms of trillium on the rocky trail is one bonus of having to watch my footing.

As English colonists began to push forward onto their lands, the Abenaki pushed back.  The result was a series of raids and Abenaki-colonial skirmishes:  Lovewell’s War, also known as Father Rale’s War or the Three Years War.

In 1724, the Dunstable attack, along with a raid in Berwick, Maine, provoked a call to arms in Massachusetts.  From Dunstable, Captain John Lovewell set out for the wilderness on the first of three Indian-hunting trips. This first expedition netted three scalps and 200 pounds. On the second, they killed 10 Indians, picked up 1000 pounds in bounties, and earned accolades for preventing Abenaki attacks on settlements.

But the third trip, in the spring of 1725, was not a charm.  In Fryeburg, Maine, Pequawket Indians led by Chief Paugus ambushed Lovewell and his command.  Lovewell and eight of his men were killed, as was Chief Paugus, at this so-called “Battle of Pequawket.”

Thus, a few months later, Captain Willard, of Lancaster, Massachusetts, set out for the wilderness, intent on killing Indians. Traveling up towards Cusumpy Pond (Squam Lake), the Willard and his company followed the Merrimack River watershed.  Along the rivers and streams, they found evidence of Indian camps and activity  — a wigman, canoes, hoops for drying beaver furs –but no people.

Although they probably had to push through some spruce and fir to see Mount Hancock, the Pemi and Mount Washington, Willard and company would have seen pretty much the same view, minus the snaking course of the Kancamangus Highway.

Although they probably had to push through a wall of spruce and fir to find this northern view from the ridge of Mount Osceola, Willard and his men would have seen same landscape, minus the snaking course of the Kancamangus Highway.

Fast-forward 150 years, to 1881, when Charles Fay publishes an Appalachia article which explains how an Appalachian Mountain Club committee analyzed Willard’s journal and concluded that Willard and his men traveled to the southern range of the White Mountains, then marched up the Pemigewasset River and along the Hancock Branch before climbing  over Osceola to the Swift River and thence to the Saco, which they followed to the coast to return home (see map below).

As I descend from the main peak towards East Osceola, I take in views of the Pemigewasset Wilderness, Mount Hancock, Franconia Ridge, and, in the distance, Mount Washington and the Presidentials.  Did Willard and his company from more settled Massachusetts marvel at the unbroken wilderness spread before them? Were they afraid, that they might end up forever lost in these mountains, or that they might meet the same fate as Lovewell?

The chimney. I climbed up this side because the rocks offered plenty of foot and hand-holds, but I was glad for another option on the climb down.

The chimney. I climbed up this side because the rocks offered plenty of foot and hand-holds, but I was glad for another option on the climb down.

I continue hiking down to the col, as maybe they did.  When I approach the “chimney,” I follow my guide’s advice and scramble down the left side.  Climbing up towards the peak, I try to imagine what it was like to bushwhack through the forest before a trail existed.  Willard had a Mohawk guide who wasn’t familiar with these mountains, but likely knew how to find the best route for traveling along the ridges, streams, and rivers.

The mile between the two peaks flies by.  Soon  I arrive at the large rock pile marking East Osceola, in the midst of an airy grove of spruce and fir.  Glad that I pushed myself to get here.

From this point, Captain Willard continued to march east. The men would have picked their way down the steep eastern side of Osceola, and then found their way to the Swift River.

The East Osceola summit.  No views, but the tree grove is a peaceful place.

The East Osceola summit. No views, but the tree grove is a peaceful place.

My car demands that I turn back towards the main summit.  On the return trek, I again take in the views.  Beyond Franconia, I can see the Cannonballs and what I’m pretty sure is Cannon Mountain because of the man-made structure on the top.  And in the distance: is that Camel’s Hump in Vermont? Also, that shadowy flat-topped mountain — could it be Mount Mansfield?  For these few miles of travel, a great rate of return.

Willard and his men never encountered or killed any Indians.  Although beset with illness and injuries (an ax to a leg,  fevers, and the “bloody flux”), it appears that all made it home safely.

Boulders and rocks, rocks and boulders on the Osceola Trail down to the parking lot on Tripoli Road.

Boulders and rocks, rocks and boulders on the Osceola Trail down to the parking lot on Tripoli Road.  Willard probably didn’t have to pick his way through the rocks, as the forest floor was covered with many centuries of moss and composted forest.

Lovewell’s War concluded with a treaty signed in December of 1725.  Maybe everyone had tired of the killing.  Maybe the General Court ran out of money for the scalp bounties. Many of the Abenaki moved to Quebec as the colonial settlers pushed north into the lands of the Saco River floodplain.

On the mountain, I want to linger on the main summit, but need to keep moving to get home to family responsibilities.  I stomp down the trail, stepping over endless rocks and boulders. The last mile is always the longest.  I’m guessing Willard’s men would agree.



If I am reading the Day analysis and Willard journal correctly, Willard and company struck at Osceola from the northwest and then climbed over and down towards the Mad River.

The pink line is the Osceola Trail. If I am reading the Day analysis and Willard journal correctly, Willard and company approached Osceola from the west, climbed over it and struck the Hancock Branch, then marched over the Kancamangus Pass to the Swift River.  It seems like the route was harder than it needed to be if they had followed the rivers. But they were marching through a forbidding wilderness, so it’s amazing that they made it at all (map image from 4000footerclub.com).

Sources and resources

RT mileage on the Osceola Trail, from Tripoli Road, is about 6.2 miles to the main summit, and 8.2 miles to hit both peaks.  I would call it a moderate grade, by local (i.e. White Mountain) standards.  I probably wouldn’t include it on my recommended family hikes, but kids who are enthusiastic hikers could definitely make the climb.

Fay, Charles E. “The March of Captain Samuel Willard.” Appalachia Vol 2.4 December 1881: 336-344. Fay’s articles includes both an analysis of which mountains the expedition might have crossed in their journey over the mountains to the Saco River and also includes a reprint of the journal itself.  Bottom line: nobody really knows exactly where the party traveled, but Fay offers good conjecture on why Osceola might have been the mountain which the men traversed.

Tuckerman, Frederick. “Early Visits to the White Mountains.”  Appalachia.  Vol 15.2 August, 1921, pp. 111-127.  More commentary on the Willard journal that draws largely upon Fay’s article.

Wikipedia provides a solid account of Lovewell’s War (see “Father Rale’s War”) based upon a variety of good sources.  For an interesting summary of the Battle of Pequawet, see Robert C. Williams’s Lovewell’s Town: Lovell, Maine, From Howling Wilderness to Vacationland in Trust.  Topsham, Maine: Just Write Books, 2007.

If you enjoyed this 4,000-footer report, check out some of my other posts:

The Agony and Ecstasy of Climbing Four Thousand Footers: Mounts Willey, Field, and Tom

Brutal Beauty on Beaver Brook: Mount Moosilauke

Moriah, my Moriah: Why Did I Wait So Long to Climb Thee?

Bushwhacking on Mount Tecumseh


About Dianne Fallon

Maniacal Traveler Dianne Fallon writes from a house in the woods in southern Maine. Her interests include travel, hiking and the outdoors, and history, and she is quickly becoming an Instagram-aholic, @themaniacialtraveler.
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6 Responses to On my own on the Osceolas with Captain Samuel Willard

  1. Mary says:

    What an adventure to take alone! Fantastic photographs, Dianne…they really take the breath away, showing the height of your ascent and the huge scale & grandness of your view. Great historical detail, as well, so thanks for sharing all–


    • Thanks, Mary, for reading! I am trying to write shorter posts, because it’s the internet age (one screen of text), but it’s hard to know how much detail readers want to know or skip. I’m trying to find that in-between place, not too long but not so brief that there’s not much of anything there. It’s a challenge!

  2. Ah the adventure! Love that pic of the view with your hiking boots. 🙂

  3. Dianne F says:

    Thanks for stopping by, Colleen. I am slowly making my way up the 4,000 footers and hopefully will conquer all of NH’s 48 before my 55th birthday!

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