Highlander describes itself as a global hiking event series, with a goal of making multi-day hiking accessible, simple, and fun for everyone. The team provides the route, food, fuel and campgrounds. You show up with your gear. And some dozens of people all hike the same route, at their own pace.

When I first started backpacking, I was eager to start planning my own trips, but I didn’t exactly have a bunch of friends ready to dive in with me. I wasn’t brave enough to go alone, nor did I want to spend upwards of $2,000 on an organized trip when I was pretty confident I could plan one myself.

I signed up for Highlander because at my comfort and skill level, it provided me the perfect scenario to safely push myself outside of my comfort zone. Because of Highlander, my skillset expanded, my idea of what was possible in the outdoors expanded, and I have grown so much as a hiker since.

I had an overwhelmingly positive experience hiking with Highlander, and if you’re here because you’re considering signing up for one, my short answer is – go for it! But there are certainly some things I would’ve liked to know before my trip, so keep reading for my key notes.

1. Highlander attendees are a wonderfully diverse group of outdoor enthusiasts

Amongst our group of 60 hikers was every kind of outdoor enthusiast you could think of – we had cowboys, ex-Military, hippies, thru hikers, outdoor girlies, techy ultralight-ers, ultra-endurance athletes…

Some had never hiked before, someone hiked in jeans the entire time, and another in hi-top basketball shoes. Others had thousands of dollars worth of ultralight gear with them and an expertly-tuned kit. And most of us were somewhere in between.

Whoever you are, you belong there. Many — if not most — people were there alone and were interested in meeting others that sleep outside and carry 30+ lbs on their backs for fun.

By the end of the trip, we had built strong connections and had heartfelt conversations – some that would open me up to things I didn’t know about or had never considered. (Maybe I do wanna do a major thru-hike…)

2. The workshops and end-of-day events are top notch

I didn’t really pay much attention to the Highlander event schedule before my trip – and honestly I assumed it would be kind of gimmicky. I was so incredibly wrong.

The first night, Montana’s specialist on wildlife conflict management spoke to us about bear safety and proper bear-spray usage. He taught us about bear behavior and psychology, and how the school of thought regarding bear interaction has changed over the last century.

I cannot put into words how eye-opening this presentation was – I have been talking about it ever since.

Here is a clip of the bear spray demonstration by a wildlife biologist and large carnivore expert.

Other notables: we got a lesson from a physical therapist on strength and mobility training for long distance hiking. There was daily yoga with a passionate and inspired teacher (who also hiked with us the whole way). We heard from the CEO of ultralight brand Zpacks (and he joined us for a couple days of hiking). There were many more, each presenter awe-spiring and informative. Spending time with them on the hike was especially cool.

3. Include extra time to explore the area

The Highlander trip I attended was hosted outside of Kalispell, Montana in the Flathead National Forest, which is also ~40 minutes from Glacier National Park. I was trying to fit as much into my limited days off, flying straight from a Tahoe wedding into Kalispell the day before the trip began, then back to NYC at its end. I didn’t include time to go to Glacier – naively telling myself that the national forest would be just as scenic.

But after 3 days of listening to the other hikers talk about how breathtaking Glacier was, I realized what a mistake I had made. A new friend of mine was feeling the same, and we ultimately decided to leave the trip early so we could spend a couple nights in the park.

I am content with this decision given the circumstances – it’s not exactly cheap flying into those regional airports, and I had no idea when I’d be able to come back! But I do wish I’d been able to finish the trip with everyone. Luckily we were able to attend the brewery party at its close and celebrate.

The reality of hosting a hiking trip for 60+ people, is that U.S. national forest and park permit requirements are extremely limiting. Highlander does an amazing job designing a route with infrastructure that can support this amount of people. But if there are famous park or trails in the area you’re traveling to, make sure to include time to see them, and don’t make my mistake.

4. Bring some comfort food

I mostly enjoyed the food given out on the trip. Breakfasts were oatmeal or egg scrambles. Snacks were an assortment of local products and Serbian (I think) imports. Things like energy balls and Ritz & tuna. Meals were pastas and rice dishes.

If I had a complaint… it would be that most of the hot meals had to be cooked in a pot. And I hate doing dishes in the backcountry.

So I didn’t, and just hot-soaked it all anyway… Most was perfectly fine to eat. I was happy to have brought a couple of Mountain House meals. And a chocolate bar (always).

5. The Highlander community is absolutely incredible

I really can’t stress this enough. The people that show up are passionate, accomplished, diverse and warm. I met at least a dozen people that I still think about regularly and who have inspired me to continually push myself in my outdoor pursuits.

All in all, my trip with Highlander was a great experience. If you’re on the fence, I hope is the push you need to go for it. Feel free to reach out with any questions – I’ll be scoping out the 2025 Europe offerings!