My Bucket List: October Hike Challenge

Hiking for a Cause


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My Bucket List: October Hike Challenge


  • Short Sands Beach on the Oregon Coast.- My Bucket List: October Hike Challenge
  • Cape Falcon Hike on the Oregon Coast.- My Bucket List: October Hike Challenge
  • View from the Meissner Shelter outside of Bend, Oregon, overlooking Broken Top.- My Bucket List: October Hike Challenge
  • A short hike with my adventure buddy outside of La Grande, Oregon.- My Bucket List: October Hike Challenge
  • Looking over the John Day River in Eastern Oregon. I hiked and they biked.- My Bucket List: October Hike Challenge
  • More puppy-friendly adventures through Eastern Oregon's Cottonwood Canyon.- My Bucket List: October Hike Challenge
  • Just Jossi and I adventuring through part of the Pacific Crest Trail in the Columbia River Gorge.- My Bucket List: October Hike Challenge
  • One of my all-time favorite hikes, Munra Point, is not dog-friendly, but it offers incredible views and fun scrambles on the way up and down. Photo by Michelle Pearl Gee.- My Bucket List: October Hike Challenge
  • Can't wait to revisit my childhood favorite, Camels Hump!- My Bucket List: October Hike Challenge
  • I have yet to do the Cape Horn Lower Trail, but I plan to tackle this and more - assuming the fire danger has dissipated.- My Bucket List: October Hike Challenge
  • Any hike with views of the Cascade volcanoes is a to-do in my books!- My Bucket List: October Hike Challenge
  • I've wanted to hike through Oregon's Wallowas for the longest time, and Aneroid Lake is at the top of my list.- My Bucket List: October Hike Challenge

The temps are cooling, the days are getting shorter, and it's only a matter of time before the first snows start falling on Mount Hood...but before I get ahead of myself planning snow-ventures to come, we here at Outdoor Project are gearing up for a month-long hike challenge to raise $10,000 for the Sierra Club! With the help of Team Sierra, we're taking to the trails this October and hiking at least 30 miles each, all the while rallying our friends, family, and community to raise funds for a good cause. 

Now I'm not typically a hiker. Don't get me wrong, I spend as much time as possible outside - preferably in the middle of nowhere, remote wildernesses, or anywhere that takes me off the beaten track and away from the crowds - but those adventures are almost always from the seat of my bike or strapped up to my ski setup. It's not that I don't enjoy hiking, it's that I enjoy letting gravity help me on the way down when given the chance. Unfortunately, when partaking in gravity-fueled activities, falls are part of the game - and such was the story with an August two-wheeled crash that's left me without a functioning right shoulder and off the bike for the foreseeable future...

And so I see no better way to recover than to rediscover my love for exploring solely by foot. Plus, I get to bring my dog as I contribute to a worthy effort and reacquaint myself with the trails that I love so much! Win, win, win.

When I first moved to Oregon, hiking was how I fell in love with this incredible region; from jaunts up Dog Mountain and "trail-running" (aka hiking a bit faster and sweating profusely with a small backpack on) Angel's Rest in the Columbia River Gorge to epic hikes up the sides of Pacific Northwest volcanoes or along the stunning, rocky coastline, hiking was my introduction to my new home. It's been a little over four years now since I began exploring the PNW, and I am completely convinced that hiking through the mountains, valleys, desserts, and rainforests of the Oregon and Washington those first couple of years is the main reason I'm still here...and now I'm not going anywhere! 

As we ramp up to the beginning of autumn, I am getting more and more excited to strap on my hiking boots and hike over 30 miles in October; what's more, I'll even be back in New England to see family, and you can bet those boots will be coming with me! It felt only natural to take advantage of my favorite website (cough cough, wink wink) and make an October Hike Challenge bucket list full of both personal favorites and long-time to-dos:


New Hampshire




Goal mileage/elevation gain: 45.6 miles, 12,171 feet in total elevation gain.

*Hikes dependent on fire activity.


Feature photo by Michelle Pearl Gee.

Our goal is to raise $10,000 this fall for the Sierra Club, and we need YOUR help!

In October, Outdoor Project and Team Sierra are teaming up to hike for a cause! All you have to do is hike at least 30 miles in October and get your community to support you. It's that simple.

Learn more and join our team!


We believe good things come from people spending time outside. It’s about more than standing on the mountain top. It’s about nourishment and learning. It’s about protecting what sustains us. It’s about building relationships with the outdoors and each other. LEARN MORE and share the pledge to Adventure Like You Give A Damn.

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