Men's Journal

What better way to spend this winter weekend than biking 33 miles up 2,675 feet of hilly terrain to find a pot of chili waiting for you at the finish line? Film screenings in between powder runs and snow sports at The Big Lepowski in Utah might take the cake. It’s your call.

By Tara House and Chase Scheinbaum

Chilly Hilly, February 26-28

Bainbridge Island and Seattle, Washington

A perfect weekend awaits on Bainbridge Island in Seattle, where the Chilly Hilly has been a celebrated annual event for 36 years. The 33-mile bike ride, named “One of Four Classic Rides” in the nation by Bicycling Magazine, kicks off the cycling season in the Pacific Northwest.

The event begins on Sunday with a scenic, early-morning ride on the Washington State Ferry, across the Puget Sound from mainland Seattle to Bainbridge. Enjoy complimentary hot cider and baked goods, served by local Girl Scouts at the American Legion Hall, as well as warm bowls of chili at the finish line in support of Squeaky Wheels Cycling Cub and 10 other local Bainbridge Island charities.

The course opens at 8:00 A.M., and attendees and riders alike may enjoy the terrain until 3:00 P.M.

Day-of registration will be open under the Viaduct in mainland Seattle from 7:00 A.M. – 10:00 A.M., and from 7:30 A.M. to 10:30 A.M. at the B.I. Cycle Shop on the island.

Check out the website for more info.

Lodging Accommodations

Bainbridge Island Only

If you’re seeking a hot tub to soak aching muscles before or after the big ride and home-cooked meals in front of a crackling fire, Bainbridge Island Vacation Rentals offers everything from luxury, private waterfront homes to cozy cabins in the woods. Don’t forget to mention Cascade Bicycle Club and the Chilly Hilly to save $25 on bookings. Other accommodations can be found here on Cascade’s website.

Mainland Seattle

Check out the Kitsap Peninsula for a mainland stay, and make sure to visit Pioneer Square, the heart of old Seattle. For a trendier Seattle experience, Belltown is the way to go. Don’t forget the famous Pike Place Market.

The Big LePowSki, February 25-27

Brighton and Salt Lake City, Utah

Named for the film following you favorite shiftless layabout, The Big Lepowski is a full weekend of partying, film screenings and snow sports clinics. Seventy-five bucks buys you two clinics, lunch, and a lift ticket to Brighton resort. That’s over 1,000 acres of the Wasatch’s best natural slopes and a terrain park spanning nearly 2,000 vertical feet.

Backcountry basics, avy skills, splitboarding, and park tricks are just a few of the topics covered by the pros on hand. Just make sure to bring your own gear (including cameras or avalanche gear if you’re taking those classes).

Try the Porcupine Pub and Grille for an off-mountain skier hangout with plenty of tap beers from Utah’s emerging micro breweries. Or, for an unforgettable fish burrito hit vaunted local favorite Lone Star Taqueria just a few minutes from the mouth of Big Cottonwood Canyon. Click here to see a map.

If you prefer to eat and drink in the dark — while watching a movie on the big screen, that is — Brewvies Cinema Pub has what you’re looking for, with booze and games to boot.

Register here in advance for the event, or show up at 8 A.M. to register in person at Brighton. Find video footage from last year’s Lepowski here.

Lodging and Accommodation

Brighton Lodge, just steps from the lifts at The Big LePowSki venue, is certainly close to the action. Try Mount Majestic Properties for other options in Big Cottonwood and other nearby canyons, or, for an urban, boutique-y hotel experience, check out downtown Salt Lake’s Hotel Monaco, with rooms starting at about $140 per night.

Fly into Salt Lake City International Airport from most major airports. Make sure to get there by Thursday evening for LePowSki’s kickoff backcountry film festival held downtown.