Best Reasons to Become an Overland Summers Trip Leader
Spending a summer as a Trip Leader with Overland may just be the most fun job on the planet. Getting...
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
Available
This departure of this trip has good availability. Apply as soon as possible since availability changes quickly.
Limited
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.
Waitlist
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.
Questions?
Call (413.458.9672) or email (info@overlandsummers.com). We look forward to hearing from you.
Blog
The World’s Beauty & Promise: Stories from the Overland Community
The Top Three Things Overland Summers Looks for in a Summer Trip Leader, And How to Win the Job
Spending the summer outdoors with kids and teens on a hiking or backpacking trip is a dream job for many...
Leading in the Sierras
“I love middle schoolers! They are so goofy, energetic, and eager to learn.” Overland leader Tiana took a break from...
Looking Ahead: 2021 Perspectives from Trip Planning
Overland's Trip Planning team—Meg Pritchard, Will Parmacek, Dave McCahill, and Ben Grannis—recently shared their thoughts on Overland’s 2021 plans with...
Looking Ahead: 2021 Perspectives from Leader Hiring
Overland's founder and director, Tom Costley, recently chatted with Beth Larcom and Luke Costley, the Overland leader hiring team, to...
Looking Ahead: 2021 Perspectives from Admissions
Overland's founder and director, Tom Costley, recently sat down with the Overland Admissions Director, Emily Ferrell, to discuss her leadership...
The Certainty of Each Other
Meg Pritchard, a member of our year 'round team, shares some reflections on Overland in these unprecedented times. At Overland,...
Spotlight: Amy Selinger — Overland Student, Leader & Parent
When the Selingers invited Overland founder Tom Costley to give a slideshow back in 1984, they probably didn’t think their...
Dessert Circle
Every evening, on every Overland trip, students and leaders sit down (with a sweet treat, of course) to recap the...
How to Prepare For A Teen Adventure Trip
As any Overland student knows, preparing for an outdoor adventure trip can be a bit nerve wracking. Whether you’re embarking...