Pack your passport and credit card but keep your panniers light for this six-day mission through the most majestic scenery south of Alaska. Start in Whitefish, Montana, where you can pick up a Jamis bike, panniers, tubes, a pump, and Clif Bars at Glacier Cyclery (rentals, $160 per week), then head east to Glacier and the classic, old-school Lake McDonald Lodge, 11 miles into the park on the famous Going to the Sun Road (doubles, $127). The next day, things get steep and twisty: ride east up Going to the Sun, a 50-mile, switchback-filled monster that climbs on a 6 percent grade before topping out at the Continental Divide, at 6,646-foot Logan Pass. Set out early—you need to reach Logan before 11 a.m., when the road closes to ascending cyclists until 4 p.m. It’s all downhill from there to the east side of the park, where you can crash at St. Mary Lodge (doubles, $149) and load up on huckleberry pie at the Park Café. The following day, ride 27 miles to the border crossing at Chief Mountain, then another 19 to the Prince of Wales Hotel, a six-story chalet on the shores of Waterton Lake (doubles, US$234). Take a day to hike around Waterton (try the 7.5-mile Bertha Lake out-and-back), then head south, crossing back into Glacier. Spend your last night at the Many Glacier Hotel on Swiftcurrent Lake to complete your tour of the grand chalets (doubles, $149), and fill up on rib eye—28 ounces of it—at the nearby log-walled Babb Bar Cattle Baron Supper Club. On your final day, catch a complimentary shuttle back over Going to the Sun (climbing it once is enough) from the St. Mary Visitor Center to the town of Apgar, then coast back to Whitefish.