Ultimate Beginner Backpacking Trip Stories: 5 Real First Trips and What They Teach
The best beginner backpacking trip stories are real ones: Robert Louis Stevenson’s 1878 trek with a donkey, Cheryl Strayed’s first trip on the Pacific Crest Trail, Bill Bryson’s Appalachian Trail attempt, Jennifer Pharr Davis’s first thru-hike, and Dan White’s novice memoir.
Each shows a first-trip mistake and a simple fix.
Backpacking trip stories are the quickest way to learn what a first trip really feels like. Guidebooks list gear.
Memoirs show the morning a pack will not budge, the day a boot falls apart, and the day a beginner keeps walking anyway.
The five stories below are all in print, from an 1878 walk through southern France to a 2008 memoir about two novices on the Pacific Crest Trail.
Each has a book you can read and a plain lesson you can use on your own first trip.
Why Backpacking Trip Stories Help Beginners
Backpacking trip stories show the mistakes beginners really make, so you can avoid them on your first overnight trip.
A gear list cannot tell you how heavy a pack feels at mile eight. A story can.
Every writer below began as a beginner at something: carrying a pack, treating water, reading a map, or simply being outside for days at a time.
Their mistakes are useful because they are specific.
We picked five true backpacking trip stories, each with a published book, so you can check the details and keep reading.
Robert Louis Stevenson: Learning to Pack in 1878
In 1878, Robert Louis Stevenson walked 12 days through France’s Cévennes with a donkey named Modestine, and Travels with a Donkey is one of the earliest accounts of recreational camping.
Stevenson was in his late twenties and still short of money.
He wanted material for a book, so he set off on a solo trek of about 120 miles (200 km) through the mountains of south-central France.
His first problem was how to carry his belongings.
He had a special sleeping bag made, so large and heavy that it needed a donkey to carry it.
He bought Modestine for the job, then found her stubborn in ways he never quite mastered.
Few backpacking trip stories are older than this one. Locals often mistook him for a peddler.
Some were horrified that he slept outdoors and warned him about wolves and robbers.
The lesson is a beginner’s oldest one: before you worry about the view, work out how you will carry what you own.
Stevenson’s book, Travels with a Donkey in the Cévennes, appeared in 1879 and is funny about every minute of it.
Cheryl Strayed: The Pack She Called Monster
In 1995, 26-year-old Cheryl Strayed started the Pacific Crest Trail with no backpacking experience and a pack she could not lift, the story she tells in Wild.
Strayed had never seriously hiked or carried a pack.
Four years after her mother’s death, and with her marriage ending, she resolved to walk the trail alone.
On the morning she was due to start, she tried to lift her pack in a motel room and could not move it.
She has said she wondered how she could carry it more than a thousand miles if it would not budge indoors.
She called the pack Monster. Her boots were too small and cost her toenails. She filled her stove with the wrong fuel.
By one review, she carried a compass she did not know how to use.
The hike turned. She sent weight home, burned the books she had finished, and kept walking.
She covered about 1,100 miles, from the Mojave Desert in California to the Oregon-Washington border.
Among modern backpacking trip stories, this is the one most beginners have heard of. Read Wild for the honesty.
The practical lessons are plain: test your pack at home, fit your boots in person, and practise with your stove before you leave.
Bill Bryson: The Overloaded Start
Bill Bryson and his friend Stephen Katz began the Appalachian Trail overloaded and out of shape in 1996, and quit before the end, as told in A Walk in the Woods.
Bryson spent an afternoon in an outfitter’s shop, he writes, impressed and bewildered by gear talk.
Then he and Katz flew to Georgia in March and set off north from Springer Mountain.
Both packs were heavy, and the first day was hard. Bryson reached the top of Springer Mountain too tired to enjoy the view.
Katz coped by throwing things away. A review describes him flinging most of his food off a cliff on the first day.
On a later stretch he tossed clothes, food and even drinking water to lighten his load.
A scale map in a shoe store showed Bryson how little of the trail they had covered.
After several weeks they rented a car to skip part of Tennessee.
This is the story to read if you worry about not finishing. They did not finish, and Bryson says so openly in A Walk in the Woods.
The lessons: the first week is the hardest, pack only what you can carry comfortably, and set a goal you can adjust.
Jennifer Pharr Davis: A First Trip Alone at 21
Jennifer Pharr Davis grew up day hiking but had never backpacked before she set off alone on the Appalachian Trail in March 2005, aged 21, as told in Becoming Odyssa.
Pharr Davis grew up in the North Carolina mountains, where her parents took the family day hiking.
She did not start backpacking until after college, when she decided to hike the Appalachian Trail.
She left Springer Mountain, Georgia, in March 2005 and spent about five months on the trail.
She chose the trail name Odyssa, and she later described herself as naive when she began.
What she took away was simplicity.
She has said she learned the value of living with less, an important lesson at 21 because it changed what she wanted from life.
Her memoir, Becoming Odyssa, came out in 2010.
She later set the overall speed record on the same trail, finishing in 46 days, 11 hours and 20 minutes in 2011.
Her account sits well beside the other backpacking trip stories here.
The lesson for a beginner: you can start with limited experience if you build skills as you go, accept help from other hikers, and let the trail teach you what you actually need.
Dan White: Two Novices on the Pacific Crest Trail
Journalist Dan White and his girlfriend set out on the 2,650-mile Pacific Crest Trail as novices, and his 2008 memoir The Cactus Eaters turns their mistakes into comedy.
White was 25 and working a newspaper job in Connecticut when he headed west.
His and his girlfriend’s hiking history was a few day trips and an aborted attempt on the Connecticut section of the Appalachian Trail.
They started with grossly overloaded packs, a faulty water filter and a camera with no film.
Along the way White lost equipment, including his waste shovel, and got lost more than once.
The book is named after the day he bit into a cactus without removing the spines.
As backpacking trip stories go, this one is the most open about mistakes. A trail mentor nicknamed them the Lois and Clark Expedition.
Reviewers say the book works better as a funny memoir than as a how-to manual, and that is exactly why it helps beginners: it shows what skipped preparation costs.
Find The Cactus Eaters if you want to laugh first and learn second.
The fix is simple: practise with your water filter and your map at home, where mistakes are cheap.
What These Backpacking Trip Stories Teach
The same few beginner mistakes appear in every story: too much weight, untested gear, and a goal that is too big.
| Mistake | Where it appears | Simple fix |
|---|---|---|
| Pack too heavy | Strayed’s Monster; Katz throwing food away | Weigh your pack at home and cut until you can carry it comfortably for hours. |
| Boots that do not fit | Strayed | Try boots on in person and break them in on short walks first. |
| Untested gear | Strayed’s stove; White’s water filter | Set up your stove, filter and tent in the yard before the trip. |
| Goal too big | Bryson’s scale map | Start with one night, then lengthen the trips. |
| No navigation skills | Strayed’s compass; White getting lost | Learn to read a map and use a compass before you go. |
Read side by side, these backpacking trip stories repeat the same lessons. Help runs through them too.
Strayed met other hikers who gave her advice, and Pharr Davis found a community among the people she met on the trail.
How to Plan Your First Backpacking Trip
Start with one night close to home, pack the Ten Essentials, and test everything before you leave.
Choose a Short First Route
Use these backpacking trip stories as a list of what to avoid. Pick a marked route you can shorten if the weather or your feet say so.
One night is enough for a first trip. Check the forecast before you go, and look for a place with a clear start and end.
Pack the Ten Essentials
The US Forest Service describes the Ten Essentials as a systems checklist built around two questions: can you respond to an accident or emergency, and can you safely spend a night out?
The ten systems are:
- Navigation (map and compass)
- Sun protection
- Insulation (extra clothing)
- Illumination (headlamp or flashlight)
- First-aid supplies
- Fire (starter and matches or lighter)
- Repair kit (knife, tape, spare parts)
- Nutrition (extra food)
- Hydration (extra water and a way to treat it)
- Emergency shelter
Read the full list on the Forest Service page or REI’s Ten Essentials guide.
Test Your Gear at Home
Every story above went wrong somewhere a home test would have caught. Pitch the tent in the yard. Light the stove.
Run water through the filter. Wear the loaded pack around the neighbourhood.
Tell someone your route and when you expect to return.
Treat any water you take from a stream or lake, because the Forest Service says to treat all trail water.
Do not count on cell coverage in remote areas, and expect the weather to change fast at higher elevations.
Leave No Trace
Follow the seven Leave No Trace principles, which start with planning ahead and end with being considerate of other visitors.
The National Park Service summary is a good short read.
Book References for Backpacking Trip Stories
Every one of these backpacking trip stories comes from a published book, and each title below links to a page where you can read more.
- Travels with a Donkey in the Cévennes by Robert Louis Stevenson, 1879. A 12-day walk through France in 1878.
- Wild: From Lost to Found on the Pacific Crest Trail by Cheryl Strayed, 2012. A first backpacking trip in 1995.
- A Walk in the Woods: Rediscovering America on the Appalachian Trail by Bill Bryson, 1998. A 1996 attempt by two beginners.
- Becoming Odyssa: Epic Adventures on the Appalachian Trail by Jennifer Pharr Davis, Beaufort Books, 2010 (review). Her first thru-hike in 2005.
- The Cactus Eaters: How I Lost My Mind and Almost Found Myself on the Pacific Crest Trail by Dan White, HarperCollins, 2008.
For safety and ethics, see the Forest Service essentials page, REI’s Ten Essentials, and the Leave No Trace principles.
Backpacking Trip Stories FAQ
Quick answers to common questions about beginner backpacking trip stories and first trips.
Which backpacking trip stories should beginners read first?
A Walk in the Woods by Bill Bryson is the easiest place to start.
It is funny, and it shows how overloaded and out of shape two beginners can be and still enjoy the trail.
For a more emotional read, try Wild by Cheryl Strayed.
What mistakes do beginner backpackers make most?
The backpacking trip stories here point to the same few: carrying too much weight, wearing boots that do not fit, using gear they have never tested, and picking a goal that is too big.
Start with one night, weigh your pack, and test everything at home.
What are the Ten Essentials?
The Ten Essentials are a checklist of safety systems: navigation, sun protection, insulation, illumination, first-aid supplies, fire, a repair kit, nutrition, hydration, and emergency shelter.
They help you respond to an emergency and, if needed, safely spend a night outside.
Do you need experience to go backpacking?
Not to start. Cheryl Strayed and Jennifer Pharr Davis both began with little or no backpacking experience, and both learned fast.
Start with a short overnight trip, build skills, and take safety basics seriously from day one.
Ask experienced friends or a local guide for help.
Did Bill Bryson finish the Appalachian Trail?
No. Bryson and Katz hiked parts of the trail, rented a car to skip some of it, and quit before the end.
He says so openly in A Walk in the Woods. Hiking part of a big trail still counts, and the book is proof.
Thinking about a first trek in Gilgit-Baltistan? Tormik Valley Tourism, based in Skardu, plans trips around your dates and fitness level.
Ready for something bigger later? See our Baltoro Glacier trek itinerary.
Start Small, Then Write Your Own Story
The best use of backpacking trip stories is to plan one short overnight trip within the month.
None of these writers began with the right gear or the right skills. They began with a trail and a reason.
Read the book that sounds most like you, weigh your pack, and book one night out.
Backpacking trip stories are best when they send you outside to start your own.
What was your first backpacking trip like, or which book would you add? Share it in the comments below.
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