How to Prepare for Your Teen Summer Hiking Trip Part Two: Making the Transition from Home to Hiking


Going on a teen summer hiking trip is incredibly exciting!

But let’s face it: it can be a bit scary, too.

You might be imagining all the fun you will have – tossing the frisbee around at camp, sharing stories on the trail, and gazing up at the stars before curling up in your tent. 

And, at the same time, perhaps you are a bit nervous about your trip.

While away from home on Overland, you will be living simply. You’ll leave your phone at home, cook all of your meals as a group, and fall into the routine of rising with the sun and falling asleep to the sound of the nearby creek. 

How can you prepare for this transition from home to hiking? It’s easy, it doesn’t take much time, and it’s fun: read on below to get good advice on making the transition from home to camp.


One of the best parts of being away on your Overland trip is taking full advantage of these opportunities to live in the moment. Overland trip planner Meg Pandiscio knows how new this might feel, and in this post, she’ll share a few ideas of how to best prepare for the different rhythms of life while away on your summer hiking trip. These are tips and tricks she’s learned over the course of four Overland summers and leading more than 100 different students. 

PREPARATION TIP #1: Go For A Walk With A Friend

While on your Overland trip, you will be spending your days almost entirely outside. 

While you may already be immersed in physically preparing for your trip, it’s important to prepare mentally and emotionally, too.

Maybe you’ve been on long hikes with your pack, or perhaps you are leaving home for the first time and have never gone hiking! Either way, spending all day everyday outside will probably feel different than life at home and in school. To prepare for this, put on your boots or sneakers (and maybe your backpack!) and go for a walk with a friend. Start to shift your mindset to time on the trails, sharing stories, breathing fresh air, and living in the moment. Take this opportunity to get excited for all your Overland trip has to offer.

PREPARATION TIP #2: Take A Break from Your Phone

Despite the overwhelming benefits of spending time without technology, it has become a constant part of our lives. Your experience on an Overland trip will be phone free (not to worry, your Overland leaders will have them for emergencies), and many students share that this was one of their favorite parts of the trip. Before leaving home, try setting your phone aside for a few hours. Make a fun plan with your friends or cook a meal with your family! You will quickly start to notice that removing your phone and outside distractions can help you engage fully with your present company.

PREPARATION TIP #3: Learn A Few Riddles to Share

Lots of Overland groups love playing trail games or doing riddles on long hikes. Try learning one to share with your group! Ask your friends or teachers if they have any fun ones to share. Try taking a peek at a library book or looking for websites with clever riddle ideas.

PREPARATION TIP #4: Spend A Night in Your Sleeping Bag

This summer, your tent and sleeping bag will quickly start to feel like home. If you haven’t already acquired a sleeping bag, your first step will be to choose the sleeping bag that is appropriate for you and your trip. Next up, try it out! The more nights you spend happily falling asleep in your sleeping bag, the more comfortable it will feel when you’re on your trip. Try hosting a campout in your living room, or even curling up in your sleeping bag in your bed.

PREPARATION TIP #5: Learn About Your Upcoming Trip

Open up your trip itinerary on your trip page of our website (here you can see what Alaska Explorer gets up to). You’ll be able to get a sense of what you will be doing, and can get in the mindset for your trip. Got questions? Reach out to the person who plans your trip (it might even be me!). My colleagues and I spend all year becoming experts in your trip; we’re a great resource! 

PREPARATION TIP #6: Talk to Someone About Your Summer

Hopefully you have taken a look at the different components of your trip, and have a long list of activities you are looking forward to! Choose the activity you are most excited about and tell someone in your life. Let them know why you are excited, and what you might learn this summer.

On the flip side, think through a day that might make you nervous, and share that as well. On the first day of the trip, your leaders will check in with you and want to know how they can best support you for the duration of your trip. If there is something you are nervous about, let them know! Your leaders will explain what the activity is, and make sure you are comfortable trying something new.

PREPARATION TIP #7: Share Your Mail Stops with Friends

All Overland trips will have mail stops – you can find these details on your family portal. Make sure to give this information to friends and family, they can write you a note or send you a postcard. Keep in mind that we ask families and friends to only send notes, and avoid sending packages. 

PREPARATION TIP #8: Write Down A Goal

Embarking on an Overland trip is a wonderful opportunity to step outside your comfort zone, try something new, and make great new friends. With that in mind, take a few moments before you head out to write down one or two goals. Maybe you are hoping to learn how to cook a meal on a backcountry stove, or go kayaking for the first time. Perhaps you have never been away from home and are looking forward to conquering the challenge of going to bed in a new place. Keep this goal in mind, and feel free to share with your leaders during your trip!

PREPARATION TIP #9: Embrace A Team Mentality

One of the best parts of every Overland trip is that you conquer each challenge as a team, nothing is a solo endeavor. From day one, you will be a key member of your team. Our leaders are there to create a cohesive, supportive, and welcoming group. They are so excited to meet you and help you form important friendships.


Learning how to prepare for a teen summer hiking trip doesn’t need to be a trial-and-error process. Meg Pandiscio’s time-tested recommendations will set you up for success this summer, and bring you a lot of joy in the process. Excellent preparation will go a long way in creating the most positive experience for you and in turn, for the rest of your Overland group.

See you on the trail!

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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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