Gear Advice for A Teen Summer Hiking Trip, Part Three

In this third post in a three-part series on getting the right gear for your teen summer hiking trip, we asked the Overland team to tell us their favorite pieces of gear.

With forty years of experience offering hiking trips worldwide to kids and teens, the Overland team is a knowledgeable source of hiking trip gear information.

Read on to learn about their favorite gear!

Sun Buff

I remember in 7th grade, I went on my first backcountry skiing trip for a late winter season ski. I forgot to put on sunscreen, and my neck and face paid the price; it felt like I was sunburned for weeks after that fateful day on Loveland Pass. Since then, I remember my sunscreen, but an added level of sun armor is my trusty buff. My love of the buff is due to its versatility — it can be used for sun protection, a dust filter, a face warmer, and most importantly, a style piece. 

Brooks Brown, Trip Planning

Hoka Speedgoat 5

From all-day hikes to trail running, I’ve traveled over five hundred miles in my first pair of Hoka Speedgoats and they’ve yet to let me down! These shoes are incredibly durable, provide lots of arch support, and give great traction on wet rocks and uneven terrain. They really are the perfect shoes for long days on the trail. I almost wish mine would start to fall apart so I can justify a brand new pair!

Jack Owens, Trip Planning

Quality Sunblock

Here’s the good stuff: Neutrogena Ultra Sheer Dry-Touch Water Resistant and Non-Greasy Sunscreen Lotion with Broad Spectrum SPF 45, TSA-Compliant Travel Size. Exciting stuff, isn’t it? But if you get sunburned at high up in the Rockies or the Alps, you’ll risk cutting your carefully planned trip short!

Tom Costley, Founder

Happy Sack

When going on backpacking trips, I never leave home without a “happy sack” – to any normal human, a happy sack is just a big, thick, plastic trash bag (or, a contractor bag). It lines the inside of your backpack, and keeps all of its contents dry when you run into any sort of precipitation. Few things feel better than having dry gear and clothes on a wet backpacking trip – hence the name “happy sack”!

Beth Larcom, Leader Hiring

Magic [Rain] Jacket

My magic jacket is, in actuality, a rain jacket, plain and simple. But to me it is far more: it’s a friend, a stowaway, a protector, and a confidante. Endlessly packable and entirely predictable; it keeps out the wind perfectly, and the rain imperfectly (but well enough); it fits like a glove, and the breast pocket fits a pair of my lightest gloves (for days when the temperature is waffling back and forth). I’ve worn it running, backpacking, and biking; as a second layer on cross-country ski days, and fourth layer on alpine days above tree line.

Luke Costley, Admissions

48oz Nalgene Water Bottle

Larger than the classic 32oz bottle, this jumbo Nalgene keeps me ultra-hydrated! Nalgenes are impact resistant, and lighter than most trendy, steel water bottles. The 48oz bottles, like other Nalgenes, are BPA/BPS free, dishwasher safe, built to last, and come with a leakproof, lifetime guarantee. This larger size is ideal for those epic hiking days that require a little extra hydration. Despite its larger size, it remains functional; the bottle fits comfortably in most hiking packs.

Alex Dunn, Trip Planning

Therm-A-Rest NeoAir Venture Sleeping Pad

Being well rested makes every other part of my life better. Sleep is like a performance enhancing drug while backpacking, and it’s almost impossible not to sleep well on the Therm-A-Rest NeoAir Venture Sleeping Pad. It’s like the Siren’s song – 100% guaranteed to bring you quality dreams.

In early 2024, David added this: My favorite thing to bring on a hiking trip are my friends: Good company makes for great memories, no matter the terrain, and scientifically speaking, distances are shorter with friends. Not only will you have more fun, but friends are likely to introduce you to your new favorite piece of gear. If you forgot something, odds are you can share theirs. Dynamic, helpful, and entertaining: they’re the ones worth going the extra mile with and for.

David Dustin, Leader Hiring

Trekking Poles

I LOVE my trekking poles. They help you move faster in challenging terrain, prevent clumsy folks like me from rolling my ankles (which I would do, often, without my trusty poles), and give your arms something to do! They also prevent my fingers from getting all swollen and puffy when I hike, and who doesn’t love that? 14ers, scree slopes, muddy trails — none of them can take me down with my poles at my side!

Marisa Wesker, Admissions

Trail Maps

Whether it’s concocting a fun trail running loop that links green spaces in a new city, or setting out on a multi-day thru hike through the Alps, I never start a new adventure without a good map. The mapping tools on Gaia GPS help me choose the perfect map for my planned route, whether it’s a set of National Geographic maps for national parks in the American West, or detailed Swiss topo maps in Europe. What I love most of all though is crowding around a table or smooth rock with a bunch of friends, and tracing our route along a trusty paper map — no screens or batteries required! 

Dave McCahill, Trip Planning

Cotopaxi Hip Pack

Being prepared during a hike with little ones is key. This hip pack allows me to be fully stocked with sunscreen, water, Band-Aids, and SNACKS all while being hands free! 

Torie Smith, Admissions

Stylish & Practical Sunglasses

Sunglasses are a safety, a style, and a comfort item. It’s no fun to miss out on a view because you’re too busy squinting, and you can seriously damage your eyes from too much UV exposure. My current favorite pair of adventure glasses are the Blenders Exposé – they protect my eyes from both the light and the wind. On top of that, they don’t fog up during activities and elevate any outdoor outfit. Pair with a hat or visor for extra sun protection!

Meg Pandisico, Trip Planning

Black Diamond Sprint 225 Headlamp

There’s nothing like a headlamp to help me walk my two dogs on dark winter mornings. Better than the flashlight on your phone, the headlamp allows you to use both hands in the dark. My Black Diamond Sprint 225 is the smallest and lightest rechargeable headlamp they make. It’s a winner!

Liz Costley, Founder

Eye Sleep Mask

Being in the backcountry is all about living a pared-down life, but I find that bringing something along that feels personally luxurious gives you an added sense of comfort. For me, my comfort is my eye mask. By blocking out light, I’m able to instantly fall asleep no matter where I am outdoors. My eye mask came in especially handy during my time backpacking in Iceland and Norway with Overland, where it’s light outside almost 24 hours a day during the summer. Between my physical need for sleep and my inability to see anything, there’s no chance of staying awake for long once I’m in my sleeping bag.

Katie Cullen, Admissions

Dr. Bronner’s Lavender Soap

When it comes to gear I can’t hike without, only one thing comes to mind: Dr. Bronner’s! It washes hands! It cleans dishes! In a pinch it’s a laxative (I don’t recommend this), toothpaste, laundry detergent, or shampoo. Plus, it smells great! Dr. Bronner’s is perfect for backpacking, a picnic, leader training, or even daily use. With a good 32 oz bottle of Lavender Dr. B’s, what could go wrong?

Outdoor Research Men’s Crocodile GORE-TEX Gaiters

Gaiters are an essential piece of gear for those looking to go on more rugged expeditions. These gaiters are perfect for keeping your legs dry, keeping debris out of your boots, and for breaking trails in tough terrain. They are easy to put on, pack down small, and can act as a great buffer between your crampons and sleeping bag. Plus, they look great! I mean who doesn’t love mid-calf socks that are loose fitting and made of GORE-TEX! A pro-tip, reinforce the bottom strap of your gaiters with some extra material (rope, duct tape, a sturdy piece of canvas) to prevent the leather from fraying as you hike. I have had mine for 10 years and they are still in great shape!

Will Savage, Leader Hiring

Darn Tough Socks

Darn Tough socks are hands down my favorite piece of gear I own. Socks feel like such a simple article of clothing yet you will never find me on a day outdoors without a pair of Darn Toughs on my feet and a pair in my pack. They are just the right thickness and texture, they hold your feet in all the right places without rubbing. No blisters here! These socks are comfortable with any pair of boots or shoes – so much so that on any given day you will find me wearing them – even just to the office. They are moisture wicking for those long days on trail or the slopes and can even act as makeshift mittens in a pinch. Darn Toughs come in different styles, think different lengths and levels of thickness, to suit the needs of every outdoors person whether it be for hiking, skiing, running, or biking. And don’t forget all of the fun colors and patterns! I truly want to collect them all. With the lifetime guarantee, I wear them thin, mail them back, and swap them out for a brand new pair and the cycle begins again.

Chelsea Colby, Admissions

Bedrock Sandals

These shoes are glued to my feet in the summer, I never take them off. They’re comfortable enough for a long day at Leader Training and durable enough to get out on the trails themselves. The straps on mine are a multicolored wave pattern, adding a little fun and color to life. My Bedrocks are seemingly indestructible, and are perfect for nearly every setting – they’ve joined me everywhere from backcountry campsites in the Adirondacks to the back of my bike in the Rocky Mountains to right here in the Overland Office. 

Lily Bianchi, Leader Hiring

Trusted backpack

Whether it’s a shorter hike with my dog or a longer one with friends, I always carry a small backpack. It provides a secure place for my keys and water, but also allows me to bring a few extras that inevitably come in handy (some Kleenex, a snack, a first aid kit, etc). It allows me to be prepared for any event and doesn’t weigh down my pockets!

Chris McAlister, Operations


The items we’ve covered in these three posts are important for Overland hiking trips for kids and teens. Take your time preparing, shop thoughtfully, and pack carefully—if you do, you’re ready to hit the trail like an Overland rockstar!


It’s the third in a three-part series.

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    Tom Costley

    When Tom Costley founded Overland in 1984, he sought to create experiences for young people that were fun, where new friendships could grow, where natural beauty was embraced, where there were real and varied challenges, and where Overland’s students would achieve something of importance to them. Overland’s focus on small groups, carefully crafted trips, and superlative leadership has made it a leader in the summer camp world. Overland’s commitment to excellence in everything it does has led to its success: over the past four decades, Overland has served 40,000 students and 5,000 trip leaders. Tom writes about the outdoors and travel from Williamstown, Massachusetts.

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