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.

Preparing for Adventure: Training Tips for Your Hiking Trip

Independence & Self-Reliance

Embarking on a hiking trip is an exhilarating and rewarding adventure. Whether you’re about to tackle a day hike or a multi-day trek, adequate physical preparation is essential for a safe and enjoyable experience. This summer, Overland students across the country and around the world will embark on trips of their own. Some will be just a week-long and stay local to the Berkshire foothills; others will be three weeks long and climb some of the world’s most iconic mountains – like Kilimanjaro!  As a trip planner for Overland, part of my job is to help students prepare for their trips by building training plans and offering guidance during their months of spring preparation. I’ve collected a lot of helpful tips and tricks over the years that serve our families well. Ultimately, I’ve found that training your body and mind before setting foot on the trail will not only enhance your endurance and strength but also ensure that you can fully appreciate the natural wonders that await you!

Continue reading to explore 7 valuable tips that will help guide your training for a hiking trip, whether it’s on an Overland trip or not; whether it’s close to home, or on the other side of the globe!

Hikers on Maine Coast Explorer take in the views during a day hike

Being active is a great starting point!

Before diving into a training plan, establish a solid routine of being active on a daily basis. Are you someone who walks to school or rides your bike around your hometown? Do you play after-school sports or compete on a team in some capacity? All of these activities will help you on your path to training for hiking. It’s also a huge help because those activities are often already incorporated into your daily schedule. By developing a strong base level of activity, you’ll be better equipped to tackle the challenges of the trail.

Break in those boots!

Next, it’s important to be comfortable in your gear. Breaking in your hiking boots is vital for a comfortable hiking experience. It allows the boots to conform to your feet, reducing the risk of blisters and discomfort. It also strengthens your feet and ankles, minimizing the chances of injuries. Our friends over at REI can’t stress this enough: take your time to gradually wear them on shorter walks before hitting the trail! Curious about what gear would work best for you? Check out some tips on how your hiking boots should fit in this blog: What gear do I need for a multi-day backpacking trip?



How to Choose a Summer Adventure for your child!

Gradually Increase Intensity and Duration

Once you have a solid fitness foundation, gradually increase the intensity and duration of your training sessions. I recently reviewed a publication from adult travel industry leaders, Mt. Sobek, which discussed the benefits of thoughtful training plans. Gradual progression allows your body to adapt and minimize the risk of injury. Incorporate uphill hiking or stair climbing to simulate the demands of hiking on inclines. Lengthen your training hikes progressively, simulating the terrain and elevation gains you expect to encounter during your trip. As you increase your training load, ensure you listen to your body and give yourself time to rest and recover.

How far should a beginner hike?

If you’re just starting your hiking journey, pick a route no longer than 5 miles on easy trails with minimal elevation gain. A good target pace is around 2-3 miles per hour. As you build strength and confidence, slowly increase the total mileage and elevation gain. The most avid hikers top out around 15 miles a day.

Emphasize Leg and Core Strength

Hiking places significant demands on your leg muscles and core stability. To prepare for the uphill climbs and uneven terrain, focus on exercises that target these areas. Squats, lunges, step-ups, and calf raises are excellent for building lower body strength. Students on our Alpine Explorer trip, for instance, will traverse the Alps this summer, and in some cases, climb – or descend – over 5,000 feet in a day. It’s important to have all those great stabilizing muscles well-prepared!

Take your backpack with you!

Carrying a backpack during your hike adds an extra challenge to your physical exertion. To prepare for this, gradually increase the weight of your backpack during training hikes. Begin with a lighter load and gradually work your way up to the weight you expect to carry on your hiking trip. This will help condition your muscles and joints for the additional strain and improve your overall endurance. How you organize the gear in your pack can also make a big difference in how easy it is to carry. If the weight is shifting around or unbalanced, the pack will feel heavier – so don’t forget to read some tips for tackling this seemingly simple task.

A camper on Rocky Mountain Expedition checks their backpack before hitting the trail.

Enhance Flexibility and Mobility

Flexibility and mobility are crucial for avoiding muscle strains and enhancing your hiking experience. Incorporate stretching exercises into your training routine. Yoga or Pilates can be beneficial for improving flexibility, balance, and body awareness. Remember to stretch before and after each training session to maintain optimal mobility.

Get Your Heart Pumping

It’s important to think about training for a hiking trip that may include high altitude hiking. You’ll need a strong heart and lungs. Incorporate interval training into your workouts. Alternate between high-intensity bursts and periods of active recovery. This will help your body adjust to the thinner air and can improve your body’s ability to utilize oxygen efficiently. 

Practice deep breathing. Diaphragmatic breathing, also known as belly breathing, can help improve oxygen uptake and promote relaxation. Incorporating breath control techniques into your training can be beneficial in adapting to high-altitude conditions.


Training for a hiking trip requires dedication and a well-rounded approach. By gradually increasing your physical fitness, building strength, improving flexibility, and familiarizing yourself with your gear, you’ll set yourself and your entire group up for a successful and enjoyable adventure. Remember to pace yourself during training, listen to your body, and give yourself ample time to rest and recover. With proper preparation, you’ll be ready to conquer the challenges of the trail and create lasting memories amidst nature’s beauty. 

Check out the training plan your Trip Planner has prepared for you in your trip’s “Before You Go” section of the website

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