We Welcome Your Application to Join Us!

We build each of our groups with care, keeping the groups small (no more than twelve students), and paying close attention to age, grade, gender, and the mix of hometowns and schools. Our goal is to put together great groups — groups where nice kids thrive in a supportive, wholesome, and caring environment. Please note: availability as shown is based on students traveling without a friend; if your child is interested in traveling with a friend, please call our office for availability.

Important Information about Availability


This departure of this trip has good availability. Apply as soon as possible since availability changes quickly.


This departure of this trip has limited availability. Apply as soon as possible, and on receipt of your application, if space is still available, we’ll confirm a spot for you. If all of the spots are taken, we’ll call you to discuss options.


This departure of this trip is currently full — please call us to discuss options.

How to Apply

Apply online using a credit card for the $795 deposit (your card will not be charged until we confirm a spot for you). Applications are reviewed in the order in which they are received (we do not hold spots over the phone).

When to Apply

The flow of applications starts in July and peaks in January/February. Some groups fill by the December holidays, and others will have space into the late spring. Our advice? Apply as soon as possible — it only takes a few minutes — and we’ll get to work right away to find a great spot for you.


Call (413.458.9672) or email (info@overlandsummers.com). We look forward to hearing from you.

The Top Three Things Overland Summers Looks for in a Summer Trip Leader, And How to Win the Job

Teamwork & Leadership

Spending the summer outdoors with kids and teens on a hiking or backpacking trip is a dream job for many people. But how do you win one of these coveted positions at a summer adventure camp?

Over the course of 40 years, Overland Summers has hired close to 5,000 summer trip leaders. Here are the top three qualifications to be a trip leader for Overland:

  1. The Right Motivation
  2. The Right Experience
  3. The Right Temperament
The Right Motivation

You have to want to spend the summer leading kids and teens! Any other motivation just won’t cut it. For example these two motivations are fine, but they’re not the right motivation to lead a teen adventure trip: “I love the outdoors!” or “I can’t wait to see the Rockies!” Make sure you understand the right reasons to be a summer trip leader.

The Right Experience

Overland wants to see that you are an exceptional leader— so we want to know: what have you led? Are you, or have you been, a sports team captain? Are you, or were you, the president of your student government? Do you run a campus organization, club, or team?

The Right Temperament

Overland’s summer trip leaders are unflappable. They are patient. They are thoughtful. They are well-organized and planful. They think two or three steps ahead, and they see the interconnectedness of their decisions: We call it playing 3-D chess.

Teen Summer Adventures Challenge 6

Ready to Apply?

Okay, Are You Ready to Apply?

You’ve thought it through, considered your motivation, experience, and temperament: are you ready to apply? If you are, then read on for tips on how to win your dream job as an outdoor trip leader for Overland.

Here are three Insider Tips to win your dream job as a summer hiking trip leader for Overland:

  1. Careful Preparation
  2. On-point Interviewing
  3. Prompt Follow Up

Insider Tip #1: Careful Preparation

  • Read the Overland website (thoroughly!). What strikes you as most important?
  • Know the mission, the history, the leadership, and the staff. Be prepared to ask good questions.
  • Network to Find current and former leaders. Learn from these people.
  • Draft, revise, and polish your application. To get past the first screen in the Overland leader hiring process, your application has to show you care, that you pay attention to details, and that you’re highly motivated.

Insider Tip #2: On-point Interviewing

If your application is picked by the Overland leader hiring team as a semi-finalist, you’ll get a chance to Zoom with an Overland staff member. Keep these ten Zoom Interview essentials in mind:

  1. Choose an appropriate setting. Don’t interview in a coffee shop! Don’t interview outdoors! Instead, sit at a clutter-free desk in a quiet room.
  2. Make sure the lighting, camera, and sound are good. Don’t wing it: test everything to make sure you’ll look– and sound– your best.
  3. Dress appropriately. Don’t overdo it (no need for a suit and tie!), but, on the other hand, a T-shirt is too casual. Strike the right balance!
  4. Be on time. Better yet, be early. Sign in to the Zoom five minutes before the appointed time.
  5. Don’t have food or drinks. This is an easy one (and, for the duration of your interview, don’t pick up your water bottle).
  6. Listen carefully. And, if you don’t understand something–especially if it’s a question, then just ask!
  7. Answer thoughtfully (and appropriately). Take your time, think it through, and do not –absolutely not– use any kind of off-color language.
  8. Be concise, on-point, and honest. This is not the time for you to indulge yourself with long, or off-point stories.
  9. Be prepared to ask three good questions. Another easy one: have these prepared ahead of time — and make sure they’re good.
  10. Thank your interviewers for their time and consideration. Take the time at the end to thank your interviewers. It’s easy. And appreciated.

Throughout the interview be yourself, relax, smile, be thoughtful, and have fun. Because that’s what we want all of our Overland leaders to do when they’re in the field leading kids and teens on a summer adventure trip.

Insider Tip #3: Prompt Follow Up

After your interview, send a followup message letting your interviewers know you appreciated their time. Keep this message brief — a two or three sentence email will do — and make it specific to your interview by referencing something that was discussed during the interview.

Conclusion: The Top Three Things Overland Summers Looks for in a Summer Trip Leader, And How to Win the Job

  1. Consider Your Motivation, Experience, and Temperament. Are you right this job?
  2. Follow our top three Insider Tips and you will have the best chance of leading for Overland. And be sure to check out this sneak peek of what it’s like to lead a trip in the Sierra Nevada.

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