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 Bike Trip Availability

Discovery & Inspiration

Sunrise on the mountains cycling on a teen summer biking trip in the Canadian Rockies

Last Updated: 3/19/20

Whether in the United States, Canada, or Europe, Overland’s bike trips offer a simple and self-powered way to explore the world and accomplish a clear goal. Traveling in a small, supportive group, led by two of Overland’s terrific leaders, you’ll carry all of your gear on your bike and learn new skills along the way. Open roads invite you, friends surround you, and the horizon awaits.

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.

Two of our trips, both designed for students just starting to bike tour, start on a Sunday and end on a Friday. Current bike trip availability is listed here:

  June 14 – June 20 June 21 – June 26 June 28 – July 4 July 5 – July 10 July 12 – July 18 July 19 – July 24 July 26 – Aug 1 Aug 2 – Aug 7
Cape Cod & the Islands
Grades 6-9     2 weeks
Limited Limited Limited Limited
Grades 7-9     2 weeks
  Good Limited Good

A girl smiling while riding her bike and wearing a helmet in from of the group in Vermont
Biking in Vermont

The rest of our bike trips start on a Saturday and end on a Thursday. Whether it’s crossing the Golden Gate Bridge or crossing the United States, our bike trips provide clear goals and destinations — and reaching those destinations is cause for celebration.

  June 27 – July 3 July 4 – July 10 July 11 – July 16 July 18 – July 24 July 25 – July 30 July 31 – Aug 6
Canadian Rockies & Montana
Grades 8-12     2 or 3 weeks
Limited | Grades 8 & 9 Very Limited (Please Call) | Grades 9-12  
Nova Scotia & Acadia
Grades 7-10     3 weeks
Very Limited (Please Call) Limited
Pacific Coast
Grades 8-10     3 weeks
Limited Good
Grades 8-11     3 weeks
Limited | Grades 8-10 Limited | Grades 9-11
European Challenge
Grades 9-12     3 weeks
Very Limited (Please Call) Very Limited (Please Call)
American Challenge
Grades 9-12     6 weeks
Very Limited (Please Call) | Dates Vary

While there may still be bike trip 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: Teen Summer Adventures / Teen Summer Bike Trips / Availability

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