Owls Head: the Most Hated Hike in the 48 (and why I loved it)

Unpopular opinion: I loved Owls Head! 

Hiked Owls Head for #33 on Saturday, and went into it expecting to completely hate it but found myself pleasantly surprised by how delightful it was – but yes, that slide does suck.

Here’s my tips for how to turn Owls Head from death march to forest frolic:


Save this hike for the Fall 
The foliage was popping this weekend, which turned boring Lincoln Woods into an enchanted, fairytale forest. 

Take both “bushwhacks”
Black Pond was not only beautiful, but saved us from the most difficult water crossings. Brutus – while still steep, was an easier descent than the slide would have been. AllTrails Pro has both bushwhacks on the map, which came in handy to find/navigate these trails.

Go when the water is low 
Or in our case, when its full-on drought conditions. I hate water crossings, but we got very lucky as they were all rock hoppable. Plus we took Black Pond both ways to avoid the biggest one, and because we liked the trail so much.

Bring a friend 
While I like solo hiking, I think Owls Head is best with friends – resort to bribery/kidnapping, if you must. Or tell them, “Don’t worry it’s flat” and then feign memory loss when you get to the slide trail.

Go when something really grinds your gears
Having a bad day/week/year? – I mean, it is 2020 afterall. There is nothing more cathartic than stomping around Lincoln Woods, waving your arms around wildly, and grunting like an animal to work out that rage.

Have a summit party 
The summit is pretty pathetic. Sad little cairn, strange little whittled stick on a tree for a summit sign. But it was fun to commiserate with other hikers about the state of the summit, and that crazy slide trail. Hikers are some of the nicest people you’ll ever meet, and I always enjoy the conversation and meeting people from this group. Shout out to all the amazing people I met up there on Saturday!

Cultivate an attitude of gratitude 
Because a day spent in these mountains is better than most days, especially this year. I am so grateful for these mountains, and the catharsis/peace they bring to me.

1 Comment

  1. Mike
    September 11, 2023

    I very much enjoyed your following sentance, as it made my day.
    “Or tell them, “Don’t worry it’s flat” and then feign memory loss when you get to the slide trail.”

    I’ve done the ‘Owl’ twice. Once, mid-way thru my 48, including continuing on to Galehead through the boot removing, muddy alley way beyond the slide. And again to complete a friend’s 48. Neither were otherwise memorable, save for the latter encountering a wedding party, that had departed after a night at Galehead: the bride and friend were wearing sun dresses, whereas, groom donning a polyester blue suit and hiking boots. The world is full of interesting people.

    Great blog writing!


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