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7 Trips You Can Take with Pro Athletes

See a cool new place and learn a tip or two from the pros along the way

If you want an adventure with a side of fanning out on your favorite pro, these destinations should do the trick. (Courtesy Wilder/Jessica Barnard)

See a cool new place and learn a tip or two from the pros along the way

What if you could combine a cool trip to someplace you’ve always wanted to go—say, Portillo, Chile, or Mount Bachelor, Oregon, or Sun Valley, Idaho—with instruction and training tips from a world-class professional outdoor athlete? It’d be that rare dream vacation that actually helps you get better and stronger at your sport instead of worse. Turns out that’s totally possible. Here are some of our favorite trips, events, and retreats, from running and mountain biking to surfing and snowboarding, led by some of the best in the game.

Train for Triathlons with Josiah Middaugh

The Westin Riverfront Resort and Spa in Avon, Colorado, offers triathlete training packages with XTerra world champion and local resident Josiah Middaugh. During the clinic, you’ll spend one hour in the hotel’s saltwater pool, one hour on a high-intensity bike trainer, and one hour learning Middaugh’s secret training tips in the gym. Afterward, you can get suggestions for exploring Vail Valley’s best trails on your own and spend the night in the Westin Riverfront’s luxe mountainside digs.

Ski with Chris Davenport

It’s called Superstars Camp for a reason: You’ll shred the steeps of Portillo, Chile, with the likes of Chris Davenport, Ingrid Backstrom, Cody Townsend, Wendy Fisher, and Mike Douglas. The next camp takes place August 4 to 11, 2018, and will see you spending a week at the iconic Portillo Hotel, located deep in the Andes, where you’ll get three meals a day, plus afternoon tea and a hot tub that overlooks Inca Lake.

Mountain Bike with Rebecca Rusch

The Queen of Pain is launching Rusch Academy this summer in her hometown of Ketchum, Idaho. The five-day camps will feature nutritionists, chefs, coaches, bike mechanics, and Rusch herself. Three separate camps, held in June and July, will focus on riding on gravel, mountain biking, and bike expeditions. You’ll spend two nights at a hotel downtown before heading into the backcountry for two nights in a plush yurt.

Go Snowboarding with Josh Dirksen

The Dirksen Derby, a banked slalom through the trees of Mount Bachelor, Oregon, was established in 2007 to raise money for Tyler Eklund, a snowboarder who was paralyzed in a crash. The event is held each December and draws both pro snowboarders and weekend warriors. Founder Josh Dirksen doesn’t compete, but sign up for the event and you’ll surely get a chance to rip a line or two with him, plus the weekend-long event includes group dinners, live music, and film screenings.

Surf with Ian Walsh

Big-wave surfer Ian Walsh and his family started the annual Menehune Mayhem event in 2003 on Maui’s Ho’okipa Beach as a way to get kids into surfing, and it has grown immensely since then, now drawing in hundreds of young people. This year’s event, which will include a youth surf competition and weekend-long festival, takes place April 7 and 8. Walsh is always around for the competition and ready to offer pointers to kids and adults alike.

Run with Lauren Fleshman

Two-time USA champion middle-distance runner Lauren Fleshman doesn’t run competitively anymore, but she does lead workshops and retreats around Oregon geared toward women through her company, Wilder, that combine running with creative writing. You’ll do interval workouts, trail runs, and yoga, in addition to working with a writing coach and eating meals prepared by an on-site chef. The first workshop is being offered in Bend this March. In fall, Wilder leads its first trip outside Oregon at a mountain lodge in Maine.

Ride with George Hincapie

At Hotel Domestique, in Travelers Rest, South Carolina, you can sign up for a group or private ride alongside pro cyclists like hotel founder and Tour de France veteran George Hincapie. They’ll lead you on some of the area’s best road rides and help pace you on the big climbs. The hotel has bike mechanics on hand to tune up your ride and a fleet of high-end rentals if you can’t bring your own.

Filed To: Oregon / Biking / Chile / Idaho / Kids / Mountain Biking / Running / Surfing / Maine / Athletes
Nicolas Henderson/Creative Commons )

San Marcos, Texas

Billed as the world’s toughest canoe race, the Texas Water Safari, held each June, is a four-day, 260-mile jaunt from the headwaters of the San Marcos River northeast of San Antonio to the small shrimping town of Seadrift on the Gulf Coast. There’s no prize money—just bragging rights for the winner. Any boat without a motor is allowed, and you’ll have to carry your own equipment and overnight gear. Food and water are provided at aid stations along the way. Entry fees start at $175 and increase as race day approaches.

The Ring

(Courtesy Quatro Hubbard)

Strasburg, Virginia

The Ring is a 71-mile trail running race in early September along the entire length of Virginia’s rough and rocky Massanutten Trail loop. To qualify, you need to have run a 50- or 100-mile race before the event and win a spot through the lottery system. Entry is free. Complete the run and you’ll become part of the tight-knit Fellowship of the Ring and be eligible for the Reverse Ring, which entails running the trail backwards in the middle of winter.


(David Silver)

Santa Fe, New Mexico

Each spring, competitors gather in Santa Fe’s historic plaza with a simple goal: be the first to reach 12,308-foot Deception Peak, 17 miles and 5,000 feet of elevation gain away. Competitors run or bike the first 15 miles to the local ski area before transitioning to their waiting ski-touring setups for the final push to the top. Time stops only when they’ve skied back down to the tailgate in the resort’s parking lot, which is funded by the modest entry fee of around $25. To add to the sufferfest, some participants sign up for the Expedition category, in which they strap their skis, skins, boots, and poles to their bikes for the long ride up. Start dates vary depending on snow conditions, but look for the event page to be posted on Facebook in late March or early April.

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