From start to finish the six greatest weeks of your life.
This trip is hard. Really hard. But it’s simple, too. Just wake up every day for six weeks, get on your bike and head west. It’s no more complicated than that.
Sharing the experience with your group and your Overland leaders makes all the difference. We can promise you this: you have never relied on the support and encouragement, the friendship and fun of any group of people as much as you will on the American Challenge. That is what makes it so great.
There are markers all along the way of your group’s steady progress toward the Pacific. Reaching the Mississippi. Rolling across the Great Plains. Climbing the Rockies. Marveling at the desert. Riding up and over the San Gabriels and into Los Angeles.
On the last day of the trip, you’ll reach the coast. You’ll sprint across the sand, front wheels in hand and dive into the crashing waves. Surrounded by trip mates with whom you have shared every day, every mile and every moment of these past six weeks, you’ll scream, yell, shout and hug. You’ll know then how hard, how simple, and how wonderful the American Challenge is.
The American Challenge was a life-changing experience. I learned so much about myself and made lifelong friends. Most amazing summer ever!
- Emily Padalino, West Sand Lake, New York
Itinerary may vary by group and is subject to change.
Days 1-6: The Atlantic and the South
We’ll meet in Charleston, South Carolina. On the first day of our ride, we’ll watch the sun rise over the Atlantic, dip our front wheels in a gentle breaker and look west to begin our trek to the Pacific. This first section of the trip will bring us to the heart of the South as we make our way across South Carolina toward Georgia and our first state line.
Days 7-12: Alabama to the Mississippi River
From Alabama, we continue west to one of America’s greatest rivers, the Mississippi. The terrain is generally forgiving as we skirt south of the Appalachians. Building to an average of 85 miles per day, we’ll grow accustomed to waking up early, riding with weight and living together as a group.
Days 13-17: Arkansas and the Ozarks
We’ll triumphantly cross the Mississippi River, the first major landmark of our trip, and enter Arkansas. Here, the rolling hills of South Carolina, Alabama and Mississippi slowly give way to short, but steep climbs through the beautiful Ozark Mountains.
Days 18-26: The Great Plains
We’ll hit our stride as we meet the sparse beauty of the Great Plains and ride through golden fields. The Rockies slowly rise above the horizon as we pedal west.
Days 27-32: The Rockies
With green, rolling hills, the Ozarks and wide open plains behind us, we’ll face our biggest challenge yet: the Rockies and the Continental Divide. High passes and snowcapped mountains, steep climbs and rollicking descents will lead us into the heart of the American Southwest.
Days 33-39: The Southwest and the Grand Canyon
Arriving in vast painted deserts, we’ll make our way to the Grand Canyon, pausing to spend a night on the South Rim. We’ll wake up and head south toward Arizona’s Black Hills.
Days 40-42: The Desert
As the final days of the trip approach, red sandstones give way to sagebrush-covered plains and the deserts of eastern California. We’ll challenge ourselves with a 111-mile ride across the Mojave Desert from Parker, Arizona, to Twentynine Palms, California.
Days 43 & 44: The San Gabriel Mountains
In California’s San Gabriel Mountains, we will climb out of the desert to an elevation of over 7,000 feet. The night before riding to the Santa Monica Pier, we’ll camp high above the lights of Los Angeles and look back on six incredible weeks of adventure, camaraderie and challenge.
Day 45: The Santa Monica Pier
On our final morning, we’ll work our way down and out of the mountains, through Los Angeles and all the way to the Pacific. When we reach the coast, we’ll sprint across the sand, front wheels in hand and dive into the crashing waves. After the Pier, we’ll go to our accommodations, pack up our bikes and enjoy a final, celebratory dinner before saying goodbye.
The group will spend about half of the trip camping at frontcountry campgrounds. Campground facilities will vary and may include flush toilets and/or showers. The remaining nights, the group will spend indoors. Indoor accommodations include churches, community centers, motels and a hostel in Santa Monica. Indoor facilities will vary and may include showers and laundry.
Things to know
- We travel light on Overland trips, please only bring items on your packing list.
- There are no reimbursements for lost, damaged or stolen items.
- Your group will have access to laundry periodically.
- Please do not bring any electronics (including your cell phone). See FAQs for more information on our cell phone and electronics policy.
- Do not bring any type of knife or multi-tool (such as a Swiss Army knife or Leatherman tool). There are absolutely no weapons permitted on any Overland trip.
- A high-visibility exterior layer is required at all times while biking. See packing item descriptions for more details.
- If you are flying to your trip start, pack your sleeping pad and bike shoes in your bike box or checked bag and take your helmet and sleeping bag with you on the plane as carry-on items in case your checked luggage fails to arrive on time. Pack all remaining items in a duffel bag or in your panniers (you can tape or strap your panniers together to check them as one piece of luggage).
- Pair of Panniers
Students should bring all belongings to the start of the trip in the panniers they will use this summer. Panniers are saddlebags sold in pairs that attach to either side of your rear rack. You will want large panniers, 2400-3000 cubic inches total (for the pair), designed for touring. One large pannier has internal dimensions of approximately 17" x 13" x 7". You should be able to fit all of your belongings, besides your sleeping bag and pad, into your two panniers and have some space for group gear. Consider compressibility of clothing while packing for your Overland bicycle tour.
- Synthetic High Visibility T-Shirts (3) & Vest (1)
A high-visibility exterior layer is required at all times while biking. On warm days a high-visibility t-shirt will be sufficient. The vest should be large enough to wear over warm layers while riding on cooler days. Please visit the Overland Store if you need to purchase these items and for an example of high-visibility apparel. High-visibility bike jerseys are acceptable but not necessary.
- Bike Shorts (3)
Biking specific spandex shorts with a padded seat called a chamois. Bike shorts fit snugly in order to reduce chafing and discomforts from sitting on a bike seat for long distance rides.
- Shorts (1)
Athletic or comfortable shorts to wear around camp
- Athletic Socks (pair) (5)
- Wool or Synthetic Socks (pair) (1)
- Synthetic T-Shirt (1)
Short-sleeve shirt or tank top
- Underwear (4)
- Swimsuit (optional)
If we swim, many students will wear shorts (and a sports bra for girls).
- Waterproof Raincoat
Waterproof material required (not just water resistant). Note that a high-visibility exterior layer is required at all times while riding and will be worn over your raincoat. Raincoats provide protection from wind and rain and serve as an extra warm layer. Your jacket should be large enough to allow layers underneath. We recommend hoods and breathable materials. Gore-Tex is a well-known waterproof and breathable fabric but there are many other quality fabrics. Ponchos are not acceptable.
- Lightweight Fleece Jacket or Pullover
- Water Bottles (2) & Hydration System
A 24 ounce bike bottle is a good size to aim for but a smaller size is okay (it just needs to fit in a standard bike water bottle cage). For a hydration system the simpler the better—the pack is used primarily to carry water. If it's too big or filled with other items, it will be uncomfortable to wear all day. A 70-100 ounce (2-3 liter) bladder inside a small backpack (e.g., CamelBak) is a good size to aim for in addition to other water bottles
- Sleeping Bag
A lightweight, compact sleeping bag rated to 30 degrees Fahrenheit or less. We recommend either synthetic or down material. Your sleeping bag should compress into a stuff sack no larger than 20" in length.
- Sleeping Pad
Full or ¾ length compact sleeping pad. We recommend closed cell foam that is thin and firm (e.g., RidgeRest) or self-inflating (e.g., Therm-a-Rest).
- Bowl, Mug & Utensils
6" to 8" plastic dish or bowl with top, insulated plastic mug, spoon, fork and knife. These don't need to be special camping utensils - for example, a Tupperware dish and regular eating utensils are fine.
- Headlamp & Extra Batteries
- Touring Bicycle & Rear Rack
One of the following bikes is required: Trek 520, Surly Long Haul Trucker, Fuji Touring, Jamis Aurora, Novarra Randonee. These bikes must be in excellent condition and have been purchased in the past 48 months. Other bicycles will not be accepted. Please see the Right Bicycle for Your Overland Trip for more information about acceptable bikes and traveling with your bike.
- Bike Helmet
If you are flying to trip start, carry your helmet on the plane with you
- Rear Bike Light
A rear bike light is required when riding in low light conditions. The light should be battery powered with a variety of mounting options (clipping on to a pannier or a rear rack, for example). The Portland Design Works Radbot 1000 and the Planet Bike LED Superflash turbo are two examples of bike taillights.
- Bungee Cords (4)
These should be 18-24" in length. Bungee cords are included with an Overland bike rental.
- Spare Bike Tire (1)
- Spare Bike Tubes (4)
Spare tube that matches your bike's tire size. Note: you may choose to start the trip with just two tubes and mail the other two ahead to one of the mail stops. On average, students on the American Challenge get 6-8 flat tires throughout the trip. Some punctures can be easily repaired with a patch, but other times putting in a new tube is a better option. Although four spare tubes may seem like a lot, many students use all their spares and some need to purchase more along the way.
- Spare Bike Spokes (4)
Spare spokes that fit your wheels (two front and two rear) including the spoke nipple. Ask your local bike shop for guidance.
- Tire Patch Kit
- Set of Tire Levers
- Spare Set of Brake Pads (1)
- Water Bottle Cages
Attached to the bike frame. Some smaller size bike frames can not accommodate two cages. That's okay, as you'll be able to strap additional water bottles to your rack with your other gear. All Overland rental bikes come with water bottle cages.
- Bike Gloves (optional)
Well-padded for comfort
- Chamois Cream (optional)
Special cream to put on your bike shorts chamois to reduce the risk of chafing and saddle sores. Some popular brands are Chamois Butt'r and Assos. You can purchase chamois cream at any bike shop.
- Shoes for Biking (pair)
Bike touring or mountain biking shoes with bottom treads and "clipless" recessed cleats. A popular style of clipless shoes and pedals are SPDs. Please do not bring racing shoes since they have hard soles that are uncomfortable to walk in.
- Camp Shoes (pair)
Closed-toe shoes to wear around camp. Crocs or lightweight tennis shoes are ideal.
- Photo Identification
A current school or other kind of photo identification (if you have one)
- Synthetic Camping Towel (1)
A medium size synthetic camping towel. Synthetic towels are lightweight and dry much faster than regular towels.
- Gallon Sized Ziploc Bags (10)
To organize and waterproof your gear and small items
- Large Trash Bags (5)
To waterproof your gear
All items should be travel size. If necessary, you will be able to restock during the trip.
Polarized sunglasses that wrap around to protect from glare are ideal
- Sunscreen (SPF 15+) & Chapstick (with SPF protection)
- Insect Repellent
- Camera, Charger & Extra Batteries (optional)
A digital or disposable camera and, if necessary, a charger and large enough memory card to accommodate your pictures (4 to 8 GB)
- Personal Journal or Book (optional)
- Spending Money
$30 per week in cash or a debit/ATM card. Please remember your pin number if you bring an ATM card.
What is the weather like on the American Challenge?
The weather on American Challenge varies every day. You should prepare for warm temperatures and lots of sun. The southeast is hot and humid. In Kansas, Colorado (or Oklahoma and New Mexico, depending on the group), Arizona and eastern California the temperatures are hot and the climate dry. In the mountains, temperatures will range between the 50s and 60s. Sometimes it is warm and sunny, other times it is rainy and cold. Our packing list takes these variable factors into consideration.
What are the arrival and departure airports for my son or daughter’s trip?
You will need to arrange transportation for your son or daughter to Charleston International Airport (CHS) at trip start and from Los Angeles International Airport (LAX) at trip end. We will provide more specific travel information once we have placed your child on a program.
How often will my son or daughter have access to showers and laundry?
While we have regular access to showers, most students will shower once or twice a week. Groups will do laundry once a week.
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 and other 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 for over 30 years. Please click here to read more about our approach to risk management and our accreditation by the American Camp Association.
Does my son or daughter need to have previous experience?
While no previous experience is required, we have high expectations of our students. We expect your son or daughter–with your help–to select a trip that is appropriate for their interests and abilities. You should spend some time familiarizing yourself with the details of the specific program and help your son or daughter understand what to expect. We also expect our students to prepare ahead of time: to review the packing list, gather clothing and gear and complete whatever training the trip requires (for recommended training please see the Before You Go tab). Once the trip begins, your son or daughter should be ready–and excited–to contribute to a wholesome and enthusiastic group where each group member feels welcomed and valued.
Please tell me about Overland’s admissions process.
For more information, and to access our application, please visit our Apply page.
When we receive your son or daughter’s application, if the first choice is available, you will receive a phone call and an email containing a link to our Overland Portal where you will find our Admissions Review Forms. We will accept your deposit to hold your child’s place in the program pending a favorable Admissions Review. If the first choice is not available, we will call you to confirm that the second choice is acceptable. If neither the first choice nor second choice are available, we will call you to discuss options. For those students placed on our waitlist, we will notify you as soon as a spot becomes available.
We seek to admit students who have demonstrated that they possess the personal qualities and experience necessary to succeed on an Overland trip. While Overland is always supportive and nurturing, an Overland program is unlike a traditional camp in that our small groups–12 students and 2 leaders–travel, live and work as a group, making all of their own meals, helping each other and cooperating in ways big and small, and they do all of this far from home. As a result, every student must be able to thrive in an environment that places equal emphasis on:
1. Teamwork and shared responsibilities.
2. Independence and self-reliance.
3. Support of others and consideration for others.
What is Overland’s cell phone and electronics policy?
Our programs offer the opportunity to strengthen independence and self-reliance. To maximize these benefits, we do not permit phone calls to or from our students. The exceptions to this are: (1) each student will call home on arrival and departure with our phones and assistance and (2) in the case of an emergency. Anytime a student is treated for an injury or illness by a doctor or medical personnel, parents are notified by our office. A full-time staff member calls 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 the child.
If it is important for your son or daughter to be able to call you while en route to Overland, we recommend you purchase an inexpensive prepaid cell phone. Please do not send an expensive smartphone like an iPhone or BlackBerry. On arrival we will collect all phones but we have found that safeguarding these phones is problematic because our programs move from place to place (as a result, we take absolutely no responsibility for phones, electronics or personal property brought by students, and we will not make any reimbursements for lost, damaged or stolen phones, electronics or personal property).
We are committed to providing extraordinary support to you and your son or daughter; to that end, the Overland office is staffed from 8:30 a.m. to 8:30 p.m. seven days a week during the summer (outside of office hours our answering service provides emergency coverage). Our leaders in the field are in touch with our office regularly; they carry cell phones and in some cases satellite phones.
Bike 3,000 miles across the country from Charleston to Los Angeles.
Students going on American Challenge should prepare for:
- 3000+ miles of riding
- Riding all day, beginning at first light and ending in the late afternoon or evening
- 39-40 days of biking with an average of 85 miles per day
- Travel to and from the trip
- An Overland experience
We expect you to arrive to your trip fully prepared for all activities.
Preparing for Biking
The American Challenge is Overland's most challenging trip. You will ride an average of 85+ miles over the course of 6 weeks. There are 11 days over 90 miles and seven or eight days (depending on the itinerary) over 100 miles. You will encounter challenging terrain: the Ozarks in Arkansas, the wide-open and windy plains of Kansas, eastern Colorado or Oklahoma and long mountain passes in the Rockies, Arizona’s Black Hills and the San Gabriels just east of Santa Monica. You will likely experience high temperatures (hot and humid east of the Mississippi; hot and windy across the Great Plains; hot and dry across the desert) and the good possibility of some rainy stretches. You will start riding at first light, taking short breaks during the day, and complete the day's ride in late afternoon to early evening. You will spend some days off of the bikes: arrival day, departure day plus five buffer days to allow for delays en route (most groups will find that they spend these buffer days partially or completely off of the bikes).
Overland bicycle tours are self-contained—there is no van support. You will carry all of your belongings, plus some group gear and food, on a sturdy rack mounted over the back wheel of your bike. You will hang panniers (these are saddlebags, pronounced “pan-yers”) off the rack and attach gear like your sleeping bag and sleeping pad to the top of the rack using bungee cords. On average, you will carry about 40 lbs of equipment on your bike (not including the weight of the bike).
Riding.There will always be a range of abilities in every American Challenge group. Successful groups are the ones where the stronger riders commit themselves to support the weaker riders and where the weaker riders work hard to improve their riding. For faster riders, the challenge is to slow down and enjoy the group experience of riding across America. For slower riders, it's important to pay attention to your speed on the bike during your spring training rides. If you cannot easily maintain the minimum speeds required, then you are going to have to train more—and harder—than the requirements that we have spelled out.
Pace. Let's say an easy pace for you when your bike is fully loaded is 8 miles per hour. Do the math: 80+ miles a day at 8 miles per hour = 10 hours of pedaling—when you add in stops for snacks, lunch, delays and breakdowns your 10 hours of pedaling has grown to 12+ hours. It's simply not a schedule that can be maintained, especially when the day's mileage is in the 90+ range. Plus, there will be a handful of riders who can easily maintain 16 miles per hour. In the spring, if you find that you are a slower rider, then you must work longer and harder to improve your speed and endurance.
- 12 weeks before your trip: two rides a week of one hour each (14 miles over varied terrain).
- 8 weeks before your trip: two rides a week of 90 minutes each (21 miles over varied terrain).
- 4 week before your trip: four rides a week, two of two hours each (28 miles over varied terrain) and two rides of four hours each (56 miles over varied terrain). All rides should be on fully loaded bikes with all of your gear and clothing.
All training rides that are unloaded (i.e., without your panniers, sleeping bag, etc.) must be at an average speed of 14 miles per hour (or greater); all loaded training rides must be at an average speed of 12 miles per hour (or greater). You must be able to maintain (or exceed) 12 miles an hour fully loaded on terrain that includes hills. All pre-trip training rides must be undertaken on the bike you will ride on the American Challenge and with the pedals and shoes that you plan to use, so you can be comfortable with your equipment at the start of the trip.
Preparing for Travel to and from the Trip
Families are responsible for arranging flights to and from the designated airport during a specified window (please do not purchase flights until you have received an email confirming our review of your health forms and school reference). Overland staff will be at the airport to welcome you at the start of your trip and to assist with your departure. We will have you call home upon arrival and before departure. We will provide more specific travel information once we have placed you on a program.
Preparing for an Overland Experience
Overland programs are wholesome, structured experiences with high expectations of each student’s behavior. Overland expects all students to contribute to an enthusiastic, positive group. We expect you to be helpful and supportive of your trip mates and leaders. We ask that you leave your cell phone and electronics at home (cameras are always welcome), so you can fully engage with your group and your trip. You will have the opportunity to send letters and receive mail at designated mail stops, which are shared in the spring.
All trips have a range of challenges. You should come prepared and recognize that some days will be more difficult, more challenging and longer—both in terms of miles and hours on the bike—than others. Delays occur due to a wide range of variables beyond the control of you, your group or your leaders. Weather patterns change and road conditions vary. You, or someone in your group, might get a flat tire or encounter another issue that could delay your group. On some days your group will arrive in to camp in the early afternoon, with plenty of time to explore the area or go swimming, while on other days your group will spend more time on the bike.
Arriving ready for a challenge – and prepared to contribute to an enthusiastic group – will go a long way toward creating a successful trip. Please contact us if you’d like to discuss preparing the American Challenge.