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.

What gear do I need for a multi-day backpacking trip?

Discovery & Inspiration, Independence & Self-Reliance

So, you’ve planned a multi-day backpacking trip and you’re gearing up to embark on an adventure of a lifetime. With nearly four decades of experience offering backpacking trips across 5 continents, our team came together to offer advice on the gear you absolutely need, what you can skip, and where you should splurge. We’re sharing some of our favorite gear, too, so keep reading to make sure you don’t miss anything!

Backpacking Gear Basics

Overland has over 30 unique adventure travel itineraries, and we provide unique packing lists for every combination of hiking, rafting, climbing, and more. Having the right gear is a critical part of making the most of each experience, but carrying items you don’t need can cause as much trouble as not having something you do need! We’ve honed our packing lists to include all the essentials, and nothing more.

While each backpacking destination our Overland groups explore is unique, the five core groups of equipment needed to stay warm and dry while backpacking remain the same:

  • Footwear: properly fitting (and well broken-in) hiking boots provide traction and comfort, as well as support and stability, while carrying a large backpack. 
  • Backpack: a well-balanced internal frame backpack will hold all your equipment, and distribute the weight evenly across your body.
  • Outer Layers: no matter the forecast, it’s essential to always be prepared for rain and chilly temperatures. 
  • Light and Mid-Layers: layering properly with non-cotton clothing is key to staying warm and dry in any environment. 
  • General Gear: important items, such as a bright headlamp (with extra batteries), a warm sleeping bag, and adjustable trekking poles will make all the difference. 

My 5 Step Packing Strategy

I’ve led Overland groups in ten countries, from the Swiss Summer Haute Route to the summit of Wyoming’s Grand Teton, and through those experiences on-trail I’ve seen what gear will cut it, and what won’t. Here’s a breakdown of my strategy for gearing your child up for a multi-day backpacking trip below, as well as the best gear suggestions from Overland’s year-round team. 

Step 1: Know your route and expected weather conditions

When selecting a route, it’s important to carefully research your planned itinerary. Be sure to look at expected night and day-time temperatures, typical precipitation, and terrain. If you’re new to trip planning, our guide to backpacking the Swiss Alps is a helpful primer. 

Generally speaking, the longer and more remote your route, the more equipment you’ll need: a 3-day backpacking trip exploring New Hampshire’s White Mountains will require slightly different (and less) gear than if you’ll need if you’re heading out on a 6-day thru-hike along Iceland’s Laugavegur route

Step 2: Get Recommendations from friends and trusted sources

From the helpful staff at the local outdoor retailer to friends who spend more time on the trail then they do at home, recommendations from trusted sources are the perfect way to stay up on the latest gear technology and get personalized advice. To get you started, our year round team has shared some of the gear they reach for every time they lace up their hiking boots.

Quality Sunblock

Here’s the good stuff: Neutrogena Ultra Sheer Dry-Touch Water Resistant and Non-Greasy Sunscreen Lotion with Broad Spectrum SPF 45, TSA-Compliant Travel Size. Exciting stuff, isn’t it? But if you get sunburned at high up in the Rockies or the Alps, you’ll risk cutting your carefully planned trip short!

Tom Costley

k ExmFjBL

Happy Sack

When going on backpacking trips, I never leave home without a “happy sack” – to any normal human, a happy sack is just a big, thick, plastic trash bag (or, a contractor bag). It lines the inside of your backpack, and keeps you happy when things get wet and wild out there! Dry clothes and gear means a happy Beth!

Beth Larcom

Magic [Rain] Jacket

My magic jacket is, in actuality, a rain jacket, plain and simple. But to me it is far more: it’s a friend, a stowaway, a protector, and a confidante. Endlessly packable and entirely predictable; it keeps out the wind perfectly, and the rain imperfectly (but well enough); it fits like a glove, and the breast pocket fits a pair of my lightest gloves (for days when the temperature is waffling back and forth). I’ve worn it running, backpacking, and biking; as a second layer on cross-country ski days, and fourth layer on alpine days above treeline.

Luke Costley


48oz Nalgene Water Bottle

Larger than the classic 32oz bottle, this jumbo Nalgene keeps me ultra hydrated! Unfortunately, I don’t have a particular story that comes to mind involving my water bottle – I just truly love being well hydrated while adventuring in the mountains!

Alex Dunn

Salomon X Ultra 3 Mid GTX Hiking Boots

Before leading a group of students along a section of the Appalachian Trail for Overland, I got these boots. I have YET to get a blister in them! They’re magical! These boots are sturdy, comfortable, and reliable. Highly recommended!

Annie Duryea


Therm-A-Rest NeoAir Venture Sleeping Pad

Being well rested makes every other part of my life better. Sleep is like a performance enhancing drug while backpacking, and it’s almost impossible not to sleep well on the Therm-A-Rest NeoAir Venture Sleeping Pad. It’s like the Siren’s song – 100% guaranteed to bring you quality dreams.

David Dustin

Trekking Poles

I LOVE my trekking poles. They help you move faster in challenging terrain, prevent clumsy folks like me from rolling my ankles (which I would do, often, without my trusty poles), and give your arms something to do! They also prevent my fingers from getting all swollen and puffy when I hike, and who doesn’t love that? 14ers, scree slopes, muddy trails — none of them can take me down with my poles at my side!

Marisa Wesker


Therm-a-Rest Saros Sleeping Bag: 0F Synthetic

Before leading for Overland, I’d never bought a sleeping bag before. I run cold, so I knew I needed an extra cozy bag. I’ve used this sleeping bag high in the Rocky Mountains of Colorado, in a van winter camping in Yellowstone and Grand Teton, on my favorite hike in the Berkshires, and even on friends’ floors. I’ve found my Goldilocks bag: not too hot, not too cold, but just right.

Hayden Gillooly

Step 3: Start with a packing list (or use one of ours)!

Before heading to the store, take the time to write down or print out your packing list– you’ll want to make sure you have every item on your list, and nothing more. Forgetting an essential item like a headlamp or sleeping pad can seem insignificant at home, but can turn into a real problem in the backcountry. Checking items off a list will also ensure you don’t bring far too much gear, all of which you’ll need to carry! To get you started, take a look at the following packing lists from two of our most popular backpacking programs:

Teton Challenge packing list

Rocky Mountain Explorer packing list


Step 4: Choose your Boots, Backpack, and Sleep System carefully

Once you know what temperatures, precipitation, and terrain to expect, and you’ve written or printed your packing list, prepare to invest both time and funds in the following items:

  1. Great fitting hiking boots (and hiking socks)
  2. A properly sized backpack
  3. A sufficiently warm sleeping bag and sleeping pad

We recommend purchasing the items from a local retailer. While it’s always tempting to shop online for the best prices, it’s essential that the above items fit well and meet the demands of your trip. A visit to a nearby outdoor retailer will pay huge dividends in comfort: shops such as REI generally have hundreds of models and sizes in stock to ensure a perfect fit, and offer helpful in-store advice (along with a great guarantee).

Here are our best tips for purchasing hiking boots, backpacks, and a toasty-warm sleep system: 

How Should My Hiking Boots Fit? 

The link between your body and the trail, hiking boots provide traction, comfort, and stability for your whole body while carrying a full backpack. Great fit is paramount: the boots should be snug (but never too tight), while offering just enough space to wiggle your toes slightly. A cut that wraps above (not below) the ankle will provide great stability and ankle support. Be sure to try the boots on with a good pair of mid-weight synthetic hiking socks, which will help keep your feet dry and blister-free. Perhaps most importantly, be sure to break in (wear) your boots frequently before your trip– your feet will thank you! 



How to Choose a Summer Adventure for your child!

What Size Backpack Will I Need For a Backpacking Trip?

Your internal frame backpack should have a volume between 50 and 75 liters, depending on the length of your trip and your body type. Trips between 2 and 3 days will lean towards the smaller side of this range, while trips over 3 days will need more volume to accommodate additional gear and food. Regardless of size, the pack should fit your body comfortably and distribute the weight of your gear evenly. 

In-store employees at outdoor stores can offer great advice and can even custom fit backpacks based on your body type by swapping out hip belts and adjusting strap positions. Overland groups have had good success with reputable outdoor brands such as Osprey, Deuter, and Gregory.

What is a Good Temperature For a Sleeping Bag?

To ensure a great sleep, choose a sleeping bag with a temperature rating a few degrees colder than the coldest temperatures you’ll likely encounter. If you’re camping at elevation, be prepared for slightly cooler temperatures. It’s always easy to cool a warm sleeping bag by unzipping as necessary. Overland recommends synthetic sleeping bags, which are easy to care for and, most importantly, won’t lose their warmth when wet (like goose down will). 

A comfortable sleeping pad also provides insulation and warmth: inflatable backpacking mattresses are lightweight, pack down small, and offer great comfort– but a simple closed-cell foam pad is inexpensive and reliable, and will always do the trick!


Careful planning and a well-thought out packing list makes all the difference when preparing for a multi-day backpacking adventure. Having the right gear, and the right amount of gear, goes a long way toward making your trip comfortable and fun!

Step 5: Choose Great Layers

Once you’ve secured great boots, a properly fitting backpack, and a warm sleeping bag and pad, it’s time to pack your three layering systems: base layers (lightweight) to wick moisture away from your body, mid-weight layers to insulate & keep a layer of warmth close to your body, and outer layers to shield you from wind and rain. By using these three layers in combination, you’ll stay warm and comfortable in all conditions. 

Most of these layers can be found at home: synthetic sportswear makes for great lightweight layers, and a synthetic fleece top will insulate well. No matter the forecast, it is essential to be prepared for rain. Look for quality rain jackets and pants made of Gore-Tex® or similar waterproof and breathable fabrics, which will keep you dry and comfortable even as your body is working hard in the mountains. 

Wrapping Up

With your essentials ready, you’ll need to finalize your General Gear, which is highly dependent on the terrain you’ll be visiting. When entering the backcountry, you’ll want to be prepared with tasty food and plenty of water (and a method to purify it), a cooking system and kitchen supplies, along with a well stocked first-aid kit, small repair kit, and a system to keep your food and smelly items away from bears and critters. On Overland programs, the bulk of these items are included as part of the provided “group gear”. If taking part in a guided program with an outfitter, you’ll want to double check with them (or your group mates) to ensure you’ll have all the essentials covered. 

The key items we’ve covered here are crucial for multi-day backpacking trips, and especially for kids and teens. Great footwear ensures comfort and safety on rugged terrain, while a properly fitting backpack organizes gear. Versatile light and mid-weight layers help you adapt to changing weather, and outer layers provide protection. Round out your general gear list with a sleeping bag, headlamp, and trekking poles and you’re ready to hit the trail like a pro!

Share your favorite backpacking gear item in the comments below and inspire fellow adventurers. Prepare well, equip yourself, and embark on a thrilling journey that ignites your passion for the great outdoors. Happy backpacking!


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