WHITEFISH, Mont. You’re 16. You’re wearing your lucky jeans, your friends are picking you up soon and four hours of Saturday night stretch out before you. You have the thought: "Anything could happen tonight!" You could find love; triumph, fail, change the course of your life — fate a terrifying and welcome lightning bolt that only strikes when your parental units are elsewhere. I don’t miss the skin eruptions and hyper self-criticism of age 16. But I miss the "anything!" I miss the fear. As I’ve aged I’ve become more willing to endure deep discomfort, even pain, in the name of attempting something I’m not sure I can do. There they are, the specters of failure and triumph; there it is, the anything. Not a serious cyclist, I’ve taken a couple of bicycle trips with the nonprofit Adventure Cycling Association over the years, one in Washington state following Lewis and Clark’s route in reverse, another a self-sustained six-day Intro to Road Touring trip in Central Florida. Both have been without my family and I’ve returned home convinced they would love this form of travel: fast enough to get somewhere, slow enough to see everything, nothing mediating your experience of sky and smells and landscape. I forced the issue and booked a weeklong bike trip to northwest Montana. My husband was fully in the know; our 22-year-old daughter, in the dark. (I eventually told her there was biking involved for fear of mutiny.) On July 7 we flew to Chicago and then Kalispell, Mont., the gateway to Glacier National Park and a cute resort town that aspires to be Aspen or Telluride’s chiller cousin. I like Adventure Cycling because it’s less expensive and less fancy (you’re going to wash your own dishes, erect your own tent and lubricate your own chain, which sounds racier than it is) than luxury outfits like Butterfield & Robinson. What this means is that it attracts people who are fine with that, few prima donnas and entitled jerks. This trip was $1,299 per person, plus airfare: a full week of totally vetted rides courtesy of leader Bob Westgate and his team of five guides, every meal provided by a catering staff of three, and somewhere safe to pitch your tent each night. (There were motel options; camping was sometimes on the sport fields of elementary or high schools along the way.) Plus, the company of 29 fellow riders, each with their own stories and styles. (Our 30th rider, Chris Barnes, a late addition whom we called simply "30," was a private pilot and the kind of lifelong competitive athlete who probably turned Tiddlywinks into something that could smart a bit.) Things you should know: There was a sag wagon (vehicles that carry all your gear, but also pick you and your bike up if you capitulate — in Adventure Cycling, it is summoned via a hand signal of disconsolately patting your helmet). And I didn’t adequately read the fine print. This was an "intermediate plus" trip containing a heretofore unknown term called "singletrack." I did not call the sag wagon for the singletrack, an off-road trail the width of a mountain bike that must be ridden single file and can feature rocks, tree roots, berms, gap jumps and whoop-te-doos. I did stop and hyperventilate, I did walk my bike. But I got through it. My sag experience was involuntary, on Day 6, a ride that was slated to be 66.2 miles that at Mile 44 had a 2,000-foot climb. I didn’t make the cutoff of 1:30 p.m., I rode in the truck to the mountain’s top while hoovering up great handfuls of nacho-cheese-dusted chips, then bombed gingerly down the gravel road the remaining miles into Lincoln. But I get ahead of myself. We rode five of seven days, 250 miles total, some days with as much as 4,800 feet of elevation change, mostly on dirt and gravel U.S. Forest Service roads. We didn’t have to worry much about encountering cars, except for this: In Montana, it is legal to harvest downed trees for firewood on service roads, a win-win that keeps you toasty in winter while removing obstacles from roads. What we did have to worry about was grizzly and black bears. Many of us had jingly bells on our bikes and would yell out "hey bear" if we heard a rustling in adjacent woods; some of us, including the leaders, had bear spray. No bear spray was utilized, and the bear bells must have been effective, because I saw none. It did impact mealtime and hydration breaks along the route: No food in your tent or daypack, breaks often entailed rooting around in the back of one of the rented trucks to make a peanut butter sandwich or grab a fistful of M&M’s because a bear buffet was a bad idea. Days typically started just as the sun rose, a quick toothbrushing and breaking down your tent, breakfast served at 6:30 a.m. Slow-cooked oats topped with nuts and dried fruit, veggie scrambles, sausages and bacon, etc. — this was about fueling up. Fortified, the next order of business was to make, bag and label your own sandwich, which would meet up with you at the designated lunch spot. We filled our water bottles, dropped our repacked bags on the tarp in front of the truck, checked our bikes (ABC: air, brakes and chain) and were on the road by 7:30, consulting our day maps or letting the nice lady from Ride with GPS intone turn-by-turn directions from a cellphone. Some of us started early and bombed ahead for an early finish. Others, like C.J. Whelan from Centennial, Colo., seemed to start two hours after everyone else and magically still finish early. Our Florida posse started early and finished late, sometimes spending 11 hours on the bike before pulling into camp and a hot shower. The first ride, Whitefish to Bigfork, 44 miles, eased us in, lots of paved road and very little elevation change. We arrived in funky little Bigfork, nestled at the mouth of the Swan River on the northeastern shores of massive Flathead Lake, feeling chuffed. We could do this. The second day, Bigfork to Condon, 62 miles mostly on dirt roads with a 6-mile climb near the beginning, rocked our confidence. Could we do this? Our forearms and backs were sore, our butts were in some kind of fugue state. Rolling dirt roads and a finishing stretch of paved State Highway 83 distracted us not nearly as much as the views of the Mission Mountains and the Swan Range or, if I’m being honest, the prospect of a cold one at Flathead Lake Brewing upon arrival. Adventure Cycling has rules: no earbuds; no drafting, which means shielding yourself from the wind using another rider; always wear your helmet and the reflective caution triangle on the back of your bike. At hydration stops, remove your riding gloves, use hand sanitizer, sign in, and only then is it time to snack (and apply sunscreen and bug spray). But there seems to be an unwritten rule with ACA. If you see fellow cyclists along the route, those not in your group, invite them to dinner. We annexed a small group of Taiwanese cyclists one night, a Belgian escaping World Cup madness another. A California teenager riding solo all summer in a pair of Teva sandals was with us a couple of nights. We heard their stories and shared ours as we shoveled in heaps of meatloaf and quinoa salad and something that was like a chicken pot pie with layers of rice. The third day of riding was only 44 miles but had a steep 5-mile climb and the aforementioned singletrack. You’ve seen the viral GoPro helmet videos on YouTube, the juddering ups and downs, the shale slides, the airborne bits, and you’ve thought, "Those people are nuts." Can’t disagree. Thoughts of "I could die" turned to thoughts of "I could be maimed" to those of "this could leave a nasty scar" as I got used to it. After a long bumpy downhill along Morrell Creek and some other rolling hills, we pulled into Seeley Lake Motor Lodge, proud of ourselves and in need of a huckleberry shake (a local fetish). The next day was a layover day, one filled with a quick laundromat visit, a yoga class al fresco at our campsite, a canoe paddle serenaded by a love-addled pair of loons, and more huckleberry ice cream. We got to know Karen McLarty, the group’s only other Floridian, a skydiver and triathlete from DeLand; Peter McGivern, a wise AP U.S. history teacher from Wheaton, Ill.; the warm and song-prone Toni Romp-Friesen and her legally blind but serious cyclist husband, Wil Friesen, both coffee growers in Hawaii. These were nice people, easy to hang out with for a week of big, starry skies and pristine lakes fringed by grassy meadows, craggy mountains providing an austere backdrop. The last big riding day was a walloper at 67 miles, the day I sagged at Mile 44. The lunch break that day was in the town of Ovando, pop. 50-ish with a cluster of 100-year-old buildings, the Swan and Garnet mountains framing it. It is said to be the most bike-friendly town in Montana, a stop on the Tour Divide Race. (It comes by its moniker historically: In 1897, 20 Buffalo Soldiers, black members of the 25th Infantry U.S. Army Bicycle Corps stationed at Fort Missoula, stopped there on the way to St. Louis.) Its bar, the Stray Bullet, made me feel a wee exposed in my sweaty spandex. So, onward. In Lincoln, named for the president by giddy gold seekers who rushed into the area during the 1860s, we camped on the high school field. As I wended my way to the showers, the gleaming school gym floor, a point of local pride, brought me back to indignities like pep rallies and dodgeball. With full bars on our cellphones for the first time in days, deep in my sleeping bag I heard the volleys between my husband and daughter as they looked up other bike trips. "We could do the Black Hills of South Dakota," and "What about the C&O Canal in Virginia?" Our last ride the next day was a loop from Lincoln to the Continental Divide and back. We didn’t quite make it to the 6,376-foot Stemple Pass, the conditions rough. Nonetheless, I felt triumphant. I knew they’d like it. Next year, maybe the Black Hills. We’ll see about more singletrack. Contact Laura Reiley at [email protected] or (727) 892-2293. Follow @lreiley.