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.

Current New England Trip Availability

Discovery & Inspiration

Taking a break with the group on a teen summer biking trip
Last updated: 3/19/2020

Come explore New England’s mountains, backroads, and shorelines with an Overland group this summer. Whether you’re summiting Mt. Greylock (the highest mountain in Massachusetts!), biking the length of Vermont to the Canadian border, or learning how to rock climb in Acadia National Park in Maine, your New England adventure will be full of fun and adventure. With a small group (no more than 12 students), carefully-crafted challenges, and two terrific Overland leaders, you can’t go wrong!

A group of campers ridge on the Appalachian trail while on an overland hiking trip this summer
Hiking the Appalachian trail on our Appalachian Trail Challenge teen summer adventure trip

We offer trips in New England for all age groups and challenge levels. We also offer five different types of trips in the region: introductory, for our youngest kids, hiking, biking, service & hiking, and writing & hiking trips.

We know that fitting together summer plans is a complicated puzzle for many families. While this availability chart gives you a sense of options and timelines from our end, we encourage you to call our office at (413) 458-9672 for the most up-to-date information. We are also always happy to answer any other questions you may have.

June 14 – June 20 June 21 – June 26/27 June 28 – July 4 July 5 – July 10/11 July 12 – July 17/18 July 19 – July 24/25 July 26 – Aug 1 Aug 2 – Aug 7/8
Berkshire Adventure
Grade 4 & 5     1 week
Good Limited Good Limited Limited Limited Good
New England Adventure
Grade 5 & 6     1 week
Good Limited Good Good Good Limited Limited Good
Mountains & Sea Adventure
Grade 4-6     2 weeks
Good Limited Good Limited
Maine Adventure
Grade 5-7     2 weeks
Good Good Limited
Cape Cod & the Islands
Grades 6-9     2 weeks
Limited Limited Limited Limited
Grades 7-9     2 weeks
  Good Limited Good
New England Explorer
Grades 6-9     2 weeks
  Good Good Limited
Maine Coast Explorer
Grades 6-9     2 weeks
  Good Good Limited
Nova Scotia & Acadia
Grades 7-10     3 weeks
  Very Limited (Please Call) Limited
Writing & Hiking New England
Grades 6-9     2 weeks
  Limited Limited Limited
Service & Hiking Maine
Grades 7-9     2 weeks
  Limited Limited Limited
Service & Hiking New England
Grades 9-12     2 weeks
  Good Good Good
Appalachian Trail Challenge
Grades 9-12     2 weeks
  Limited Good Good

While there may still be availability, this is the season when our trips fill quickly and options become more limited. If an Overland trip seems like the right fit for you and your family this summer, don’t wait! Send in your application to join us for summer 2020. We look forward to partnering with your family.

Filed Under: Summer Teen Adventures / Teen Adventure Trips / New England Hiking / Summer Hiking Trips

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