Challenge
Grades 10 - 12

Sierra
Challenge

Hike & Climb California!

Hike the Sierras & Climb Mount Shasta!

Every Overland trip is a carefully crafted series of challenges with clearly defined goals. Sierra Challenge is no exception. In the Sierras, the hiking offers brilliant sunshine and big views. On the American River, the rafting is exciting. And, then there’s Shasta: 14,000 feet of volcanic beauty just waiting to be climbed! At trip end, we’ll stand atop Shasta and see the world in a new light!

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“Errol had a great experience!

It was a time of personal growth and an opportunity to gain more confidence in himself as well as meet great leaders who are good role models.”

Melinda R.

Illinois

“My favorite part of the trip was…

getting to meet kids from all over the country. I made life-long friendships. “

Mackenzie S.

Massachusetts

Sierra Challenge Download

view the full itinerary

Download the Sierra Challenge Itinerary for all of the details!

Planning the journey –
Good Things to know

Group Size
The group is always small — no more than twelve students total.
Leaders
We always have carefully chosen and thoroughly prepared leaders.
Challenge
Average eight miles/day, learn technical mountaineering skills, reach 14,179 ft. above sea level.
Age Range
Groups typically have a mix of two grades (10th & 11th, or 11th & 12th grade).
Travel
San Francisco has excellent flight options (and we provide supervision on arrival and departure).
Meals
Meals are wholesome, nutritious, and varied… and they’re fun group projects.
Activities
Day hikes, backpacking, one day of rafting, and two days climbing Mt. Shasta.
Accommodations
Primarily frontcountry camping, with facilities, and six nights in the backcountry.

your questions, 
answered

With 40 years of experience, we’ve learned what works and what doesn’t when crafting a great outdoor summer experience. Our team is just a phone call or email away.

View more frequently asked questions ›

Have more questions or want to inquire about availability?
Contact Us or call: (413) 458-9672

How challenging is this trip? What do I need to prepare for?

Students going on Sierra Challenge should prepare for full days of outdoor activities led by caring Overland leaders, a multi-day backpacking trip, and a fun, supportive, and wholesome Overland experience. The group will spend 14 days hiking an average of 8 miles per day and will reach an elevation of 14,179 ft on Mt. Shasta.

We expect you to arrive to your trip fully prepared for all activities. On Sierra Challenge, you will hike on well-established trails over a wide range of terrain, from meadows to hills to mountains. You’ll start with day hikes where you’ll carry just the essentials for the day (snacks and lunch, water, a hat, sunglasses and sunscreen, bug spray, and a raincoat). As the group’s skills and fitness increase, you’ll set out on a multi-day backpacking trip. While backpacking, you will carry all of your belongings (clothes, sleeping bag, and pad), some group gear, food, and water. Typically when backpacking, pack weights average about 30% of a hiker’s weight. In the month before your trip, you should break-in your hiking boots (wear them a lot!) and complete the pre-trip training (see below). 

All students must complete the required training program for this trip:

  • 4 weeks before your trip: three 60-minute hikes or walks in your boots
  • 3 weeks before your trip: three 90-minute hikes or walks in your boots
  • 2 weeks before your trip: three 2-hour hikes in your boots with a backpack loaded with 20% of your body weight
  • 1 week before your trip: four 2.5-hour hikes in your boots with a backpack loaded with 30% of your body weight

Overland trips are wholesome, structured experiences with high expectations of each student’s behavior. Arriving ready for a challenge — and prepared to contribute to an enthusiastic group — will go a long way toward creating a successful trip. You are expected to be engaged, positive, helpful and supportive of your trip mates and your leaders. During your trip, your leaders are there every step of the way to make you feel supported, cared for, and loved. Finally, we ask that you get excited to live simply – leave your cell phone and electronics at home (cameras are always welcome) so you can fully engage with your group and your trip. Please contact us if you’d like to discuss preparing for your Overland trip.

What kind of gear do I need to bring?

Students are responsible for bringing their own personal gear, including weather appropriate clothing, sturdy shoes & boots for hiking, and a suitable daypack and/or backpack. Clothing should include moisture-wicking base layers, mid-layers for warmth, and windproof/waterproof outer layers. Overland will provide any needed group gear, including tents, food, pots and pans, etc. You can view a detailed packing list on the Family Portal.

What do I need to know about traveling to/from this trip?

You will need to arrange transportation for your child at trip start and trip end. Getting to and from the trip is a breeze: San Francisco has excellent flight options (and our leaders will be on hand for arrival and departure). We will provide more specific travel information once we have placed your child on a trip.

What are meals like at Overland? Can Overland accommodate allergies and intolerances?

Meals at Overland

Good food (and plenty of it!), excellent nutrition, and fun are the goals of Overland’s meals. Each group buys, prepares, and eats all of its meals together. Our students, with their leaders’ supervision, prepare all meals. A typical breakfast has cereal, milk, juice, and fruit; most lunches are sandwiches (or wraps) with a variety of fillings, plus chips, and fruit; dinners reflect easily prepared group meals like pasta, burritos, and stir-frys (all of which will typically have a selection of sauces and fillings). At Overland, meals are a group experience, an important way to foster connection with and consideration for other group members.

Allergies Intolerances

We recognize there are many young people with food allergies or intolerances. We welcome these young people’s interest in joining us, and we ask parents of a prospective Overland student with an allergy/intolerance to please consider the following important information.

Most meals at Overland are prepared in basic kitchens (or outdoors), and groceries are typically purchased from small stores with limited choices. As a result, meals are prepared and served in what may be allergen-contaminated environments, and on many trips allergen-free/gluten-free foods are not readily available. While we cannot guarantee allergen-free meal settings, we will do what is reasonable to provide allergen-free/gluten-free foods on those trips where available.

In all things, our top priority is to help maintain all students’ well-being; to this end, all Overland leaders are trained to recognize and respond to allergic reactions, including administering antihistamines and epinephrine (both are carried in every trip’s first aid kit); leaders carry cell phones, and in some cases, satellite phones, so that should the need arise, emergency personnel can be contacted and their services requested. It is important for all prospective parents to understand that many groups travel in remote areas where emergency services may not be easily or readily accessible.

Our Admissions Process is Collaborative

During our admissions process, we will review all submitted Allergy Questionnaires to understand the applicant’s allergy/intolerance. We will then consider whether or not the applicant’s allergy/intolerance may be reasonably accommodated. If our admissions team has any concerns, they will contact the parent. In this conversation, we will seek to learn more about the allergy/intolerance, and we will discuss the available grocery stores, emergency services, and medical facilities on the applied-for trip. These conversations generally have one of three outcomes:

  • The applicant is placed on the applied-for trip if the applicant otherwise qualifies.
  • We offer a different trip if the applicant otherwise qualifies.
  • We recommend waiting a year and re-applying.

Managing Food Allergies/Intolerances is a Partnership

Our commitment is to the health and well-being of each of our campers. Our goal is to partner with parents and campers—a partnership in which:

We clearly describe our trips and policies;

  • Parents clearly describe their child’s allergies or intolerances and their child’s maturity level and capability to self-manage their allergy or intolerance.
  • We work together with parents in a collaborative and interactive process to determine if there are reasonable accommodations that can be made so that otherwise qualified applicants can participate in our trips.
  • Students on an Overland trip take an active role in managing their allergies, including reading food labels as needed, eating only those foods with known ingredients, and seeking a leader if a reaction is suspected.

Meals: Vegetarians Specialized Diets

Every summer there are many vegetarians who join our groups and who enjoy meat-free meals. We are happy to welcome these students as long as they understand they will share in the group’s meals but will simply have the meat portion withheld. For example: sandwiches at lunch with hummus, lettuce, tomato, and cheese (while the rest of the group has sandwiches with sliced turkey or ham); pasta at dinner with a tomato sauce (while the rest of the group has pasta with a meat sauce). We sometimes have requests from applicants with specialized diets—vegans, for example—to provide separate, specialized meals. As much as we might like to accommodate these applicants, the limitations of our kitchens, the size of available grocery stores, and the importance of group meals make it impractical to provide separate, specialized meals.

How often will there be access to showers and laundry? Will my child have to bring quarters and detergent for laundry?

Staying clean and comfortable is important at Overland!

Most trips have frequent access to hot showers. This ranges from nearly every night on some of our Introductory, Service, and Language trips, to every couple of days on many hiking trips, to longer stretches–three to five days, sometimes a little longer–on some of our more challenging trips. The goal on every trip, however, is to take showers when they are available!

In general, on every trip we do laundry once a week– this is typically in a laundromat with funds and detergent provided by Overland (and it’s usually a lot of fun!).

What are Overland’s policies on phones, electronics, and communication?

Phones

To maximize independence and self-reliance, we do not permit phone calls, emails, or text messages to or from our campers. Your child will call home on arrival and departure with our phones and assistance, and in the case of an emergency. If your child brings a phone for use while en route to their trip, please note that all phones will be collected on arrival and returned at departure. While we will take reasonable steps to prevent damage, theft, or loss to phones, we take no responsibility for phones, and we will not make any reimbursements for lost, damaged, or stolen phones.

 Electronics

Cameras are welcome but please do not bring any other electronics (e.g., iPods, iPads, Kindles or other readers, GPS or similar devices). All electronics (except cameras) will be mailed home on arrival (at your risk and expense).

Communication: We’ll Be In Touch With You If Needed

Our leaders in the field check in with our office regularly; they carry cell phones (and in some cases satellite phones). Anytime a camper is treated for an injury or illness by a doctor or other medical personnel, parents are notified by our office. A director will call the parents to explain the nature of the injury or illness, the sequence of events leading up to the injury, and/or the steps leading to the treatment. Parents are typically able to speak with the medical personnel, with the leaders, and with their child.

Please tell me about safety at Overland.

Safety and risk management are at the forefront of our decision-making–from trip planning to leader training to supporting our groups in the field.

We cannot guarantee absolute safety–no program can. All recreational activities include inherent risks. Therefore, we strive to manage the risks that we can, knowing we cannot eliminate them.

We work hard to recruit, train, and support our trip leaders so they can create the kind of trips that have made us successful since the 1980s.

Please click here to read more about our approach to risk management and our accreditation by the American Camp Association.

What is Overland's admissions process?

When we receive your application, if your first choice is available, we will:

  1. email you to thank you for your application,
  2. send you a link to access your Family Portal, and
  3. charge a deposit of $795 to your credit card.

If your first choice is not available, we will email you to discuss options.

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