Strong, Happy, Free American Challenge

American Challenge is full for this summer. Scroll down to see similar trips to explore!

American Challenge

Overview Details Itinerary What to Pack FAQs Before You Go


From start to finish, the greatest summer of your life.

This trip is hard. Really hard. But it’s simple, too. Just wake up every day for six weeks, get on the 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 our 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, we’ll reach the coast. We’ll sprint across the sand, front wheels in hand, and dive into the crashing waves. Surrounded by trip mates with whom we have shared every day, every mile and every moment of these past six weeks, we’ll scream, yell, shout and hug. And you’ll know then how hard, how simple and how wonderful the American Challenge is.

Questions? Contact us!

I never thought I could survive such mental and physical pain. I never thought I could have so much fun. Seeing our country by bike will always be one of the best experiences I have ever had.

- Lyric Abbott, Bronxville, New York
Itinerary may vary by group and is subject to change.

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.

Alabama to the Mississippi River

From Alabama we’ll 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.

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.

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.

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 exhilarating descents will lead us into the heart of the American Southwest.

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.

The Desert

As the final days of the trip approach, red sandstone gives 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.

The San Gabriel Mountains

In California’s San Gabriel Mountains we’ll 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.

The Pacific

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 a celebration at the Pier we’ll go to our accommodations, pack up our bikes and enjoy a final, celebratory dinner before saying goodbye.

Trip End

We invite friends and families to join us in welcoming groups to trip end, and we encourage parents to make plans to be with us at the Santa Monica Pier. Groups arrive around noon on the second to last day of the trip, and we spend an hour together on the beach celebrating the group’s achievements. In the afternoon groups head to the Santa Monica Youth Hostel to box their bikes, pack their gear, and spend a final evening together.

Student pick up is on the last day of the trip at 5:00 a.m. at the Santa Monica Youth Hostel. All student flights should be scheduled to depart LAX between 8:00 a.m. and 12:00 noon.


All bikes will be shipped to students’ homes via FedEx. A $100 bike shipping fee will be added to your final balance.



The group will spend about a third 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.


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Things to know

  • We travel light on Overland trips; please only bring items on your packing list.
  • 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).
  • A high-visibility outer layer is required at all times while biking. See packing 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. 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 your checked duffel bag or in your checked panniers. You can tape or strap your panniers together to check them as one piece of luggage; see luggage description for more details.
  • There are no reimbursements for lost, damaged or stolen items.
  • Please wear the navy Overland shirt that you will receive from the Overland office to your trip start location.


  • Pair of Panniers (waterproof preferred)
    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, 2,400-3,000 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.


  • Navy Overland Shirt (1)
    We will send students an Overland shirt prior to their trip, and we encourage students to wear their Overland shirt to trip start. We highly recommend this for students flying to their trip start location.
  • Synthetic High-Visibility T-Shirts (3) & Vest (1)
    A high-visibility outer layer, preferably a solid color, is required at all times while biking (high-visibility is a neon or fluorescent color, typically yellow, orange or pink). 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. High-visibility bike jerseys are acceptable but not necessary.
  • Bike Shorts (2)
    Biking-specific spandex shorts with a padded seat called a chamois. Bike shorts fit snugly in order to reduce chafing and discomfort from sitting on a bike seat for long distance rides.
  • Shorts (1)
    Comfortable shorts to wear around camp.
  • Athletic Socks (pair) (5)
  • Wool and/or Synthetic Socks (1)
  • Synthetic T-Shirt (1)
    Short-sleeve T-shirt or tank top.
  • Underwear (4)
  • Swimsuit (optional)
    If we swim, many students will wear shorts (and a sports bra for girls).

Outer Layers

  • Waterproof Raincoat
    Waterproof material required (not just water resistant). Choose high-visibility if available (a high-visibility outer layer is required at all times while riding; if your raincoat is not hi-vis then you'll have to wear a hi-vis vest over your raincoat when riding). 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

General Gear

  • Water Bottle
    A 24-ounce bike bottle is ideal (on arrival you will receive a second bottle from us).
  • Hydration System with a 2- or 3-liter capacity
    A small backpack with a bladder inside (e.g., CamelBak or Platypus) works well. If you bring a backpack, it must be a high-visibility color; if the bag is not hi-vis, you must cover it with hi-vis fabric or tape. The backpack should be designed primarily to carry water (if it is too big or filled with other items, it will be uncomfortable to wear all day).
  • Sleeping Bag
    A lightweight, compact sleeping bag rated to 30 degrees Fahrenheit or less. We recommend either synthetic or treated 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 (a Tupperware dish and regular utensils are fine).
  • Headlamp & Extra Batteries

Bike Gear

  • Touring Bicycle & Rear Rack
    One of the following bikes is required: Trek 520*, Surly Long Haul Trucker, Fuji Touring, Salsa Marrakesh or Novara Randonee**. These bikes must be in excellent condition and must have been purchased in the past 48 months. Other bicycles are not acceptable. Please see the Right Bicycle for Your Overland Trip for more information about acceptable bikes and traveling with your bike.
    * Starting in 2017, the Trek 520 will only have mechanical disc brakes. This is acceptable.
    ** The Novara Randonee was discontinued in 2017. A model from the past 48 months is acceptable.
  • 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 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 Set of Brake Pads (1)
  • 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
  • Spare Bike Tire (1)
  • Set of Tire Levers
  • Hex Wrench Multi-tool (1)
  • Water Bottle Cages
    Attached to the bike frame. Some smaller-sized bike frames cannot accommodate two cages. If this is the case, you will be able to strap additional water bottles to your rack with your other gear. All Overland rental bikes come with two 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.
  • Handlebar Bag (optional)
    Great for snacks, sunscreen and bike tools.


  • 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. You may also ride in running shoes and bring toe cages to attach to your pedals. Please do not bring racing shoes as they have hard soles that are uncomfortable to walk in.
  • Camp Shoes
    Closed-toe shoes to wear around camp. Crocs or lightweight tennis shoes are ideal.

Travel Documents

  • Photo Identification
    A current school or other kind of photo identification (if you have one).
  • Unaccompanied Minor Fee Receipt (if applicable)
    For students travelling as Unaccompanied Minors, please print a copy of the UAM fee receipt for your child's leaders to keep on file.
  • Baggage Fee Receipt (if applicable)
    Some airlines allow passengers to input credit card information to cover checked bag service charges when checking in online prior to the trip. To reduce hassle at the airport, we encourage you to pay for checked baggage beforehand and supply your child with a copy of the receipt for his or her leaders to keep on file.


  • Pre-trip Training Calendar
    Please bring your completed and signed calendar to trip start.
  • Synthetic Camping Towel (1)
    A medium-size synthetic camping towel (synthetic camping towels 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.
  • Toiletries
    All items should be travel size (if necessary, you will be able to restock during the trip).
  • Sunglasses
    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.
  • Health Insurance Card
    Please bring an original or copy of your health insurance card.
  • What is the weather like on the American Challenge?

    The weather on American Challenge varies every day, and you should prepare for warm temperatures and lots of sun as well as cooler temperatures in the mountains. The southeast is hot and humid, the southwest is hot and dry, and in the mountains of New Mexico and Colorado temperatures range between the 50s and 60s during the day, and cooler at night. 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 child’s trip?

    You will need to arrange transportation for your child 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 child 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 child need to have previous experience?

    While no previous experience is required, we have high expectations of our students. We expect your child–with your help–to select a trip that is appropriate for his or her interests and abilities. You should spend some time familiarizing yourself with the details of the specific program and help your child 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 child 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 child’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. 1. Teamwork and Shared Responsibilities. 
    2. 2. Independence and Self-Reliance. 
    3. 3. Support of Others and Consideration for Others. 

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

    To maximize independence and self-reliance, we do not permit phone calls, emails or text messages to or from our campers (the exceptions to this are: 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 Overland, please do not send him or her with an expensive smartphone; instead bring an inexpensive prepaid cell phone. 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.

    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).

    We are committed to providing extraordinary support to you and your child; 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). Anytime a camper is treated for an injury or illness by a doctor or 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.

  • Can I send mail to my child during a trip?

    Getting a letter, card or postcard while on an Overland trip is always exciting.

    Please keep in mind that sending mail to your child on an Overland trip is different than sending mail to camp because your child will be on the move. Our experience has been that mail often does not arrive on time, and, sometimes, even when it does, post offices, campgrounds and other mail stops do not reliably deliver mail to our groups. For these reasons:


    1. Please do not send anything valuable – please send letters, cards or postcards only.  If mail is late, lost or misdirected, Overland’s leaders and staff are not able to return to the post office (or other mail stop) to collect it.

    2. Please use the US Postal Service first class mail only; do not use UPS, FedEx or DHL (many of our mail stops accept US Postal Service mail only).

    3. Please do not send overnight letters: many overnighted letters arrive before or after we arrive and are then sent back (for this same reason, please do not send mail that requires a signature upon delivery).

    4. Please allow one week for postal delivery to U.S. mail stops.

    5. Please allow two weeks for postal delivery to international mail stops.

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 beginning at first light and ending in the late afternoon
  • 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 bike trip. You will ride an average of 85+ miles every day for six weeks. There are 13 days over 90 miles and six of those days are 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 and 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 pounds of equipment on your bike (not including the weight of the bike).

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 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 outlined.

Pre-trip training:

  • 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 weeks 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. You should also complete one ride of 85 miles or greater (the average daily mileage for American Challenge). All rides should be on fully loaded bikes with all of your gear and clothing.

All pre-trip training rides must be completed using the bike, pedals and shoes you will use on the American Challenge. All training rides that are unloaded (i.e., without your panniers, sleeping bag, etc.) must be at an average speed of at least 14 miles per hour; all loaded training rides must be at an average speed of at least 12 miles per hour. You must be able to maintain (or exceed) 12 miles an hour fully loaded on terrain that includes hills. Groups typically average between 12 and 14 miles per hour while riding (although pace varies by group). You will start riding at first light, taking short breaks during the day, and complete the day's ride in the late afternoon to early evening. A 12-mile-per-hour pace makes it possible for the group to get each day's miles done and have time for snacks, lunch, delays, breakdowns and essential rest and recovery.

Please refer to the Pre-Trip Training Calendar where you will record your training in the weeks leading up to trip start.

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. You are expected to be supportive of your trip mates and your leaders, enthusiastic, positive and helpful. 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.