The Mountain Shop, 355 4th Ave. (tel. 907/983-2544), rents and sells the equipment you need for backpacking or other outdoor activities in Skagway. The owner organizes guided dayhikes, backpacking trips, and kayaking trips under the name Packer Expeditions, 9th Avenue and State Street (tel. 907/983-3005; www.packerexpeditions.com). Alaska Mountain Guides, on 4th between Main and Broadway (tel. 907/983-3365; www.alaskamountainguides.com), offers rock climbing in Skagway for $160 per day and 5-day Chilkoot Pass hikes for $890 per person.
The National Park Service and Parks Canada jointly manage the famous Chilkoot Pass Trail, publishing a trail guide and offering information at their offices in Skagway and Whitehorse. Some 20,000 stampeders used the trail to get from Dyea, 9 miles from Skagway, to Lake Bennett, 33 miles away, where they could build and launch boats bound for Dawson City. Today about 3,000 people a year make the challenging hike, taking 3 to 5 days. The Chilkoot is not so much a wilderness trail as an outdoor museum, but don't underestimate its difficulty, as so many did during the gold rush.
To control the numbers, Parks Canada, 205-300 Main St., Whitehorse, Yukon Y1A 2B5, Canada (tel. 800/661-0486 or 867/667-3910; fax 867/393-6701; www.pc.gc.ca/chilkoot), allows only 50 hikers with permits per day to cross the summit. You should reserve ahead. To buy permits, call with a Visa, American Express, or MasterCard; give the date you plan to start; and specify the campsites you will use each night. Permits are C$51 for adults, C$25 ages 16 and under, plus a C$12 per-person reservation fee. You pick up the permit at the Trail Centre in Skagway; that's also where 8 of the 50 daily permits are held for walk-ins, to be distributed along with any no-shows. The reservation fee is nonrefundable, and the permit fee is refundable only until a month before the hike.
Once over the pass, you're on Lake Bennett, on the rail line 8 miles short of the road. You can walk to the road (stay safely off the tracks), or get back to Skagway on the White Pass and Yukon Route railway at 2pm Monday, Tuesday, and Friday. The one-way fare to Fraser, B.C., is $50, and the scenic 3-hour ride to Skagway is $95. The railroad requires tickets be purchased in advance, as well as meals at Lake Bennett, if you eat there. You will also need a passport to get back into the United States.
Sockeye Cycle, on 5th Avenue off Broadway (tel. 877/292-4154 or 907/983-2851; www.cyclealaska.com), leads bike tours, including one that takes clients to the top of the White Pass in a van and lets them coast down on bikes; the 2 1/2-hour trip is $79. Going up on White Pass and the Yukon Route railroad and riding back down brings the price to $179. Riders must be at least 12 years old. The company also leads a 3-hour tour of the quiet ghost-town site of Dyea for $79, going over in a van. Or ride to Dyea from Skagway on your own over the hilly, 10-mile coastal road, a very pleasant, scenic route.
Skagway, like Haines, is a good place to choose for a flightseeing trip, as Glacier Bay National Park is just to the west. Flightseeing operators offer flights from Skagway, too. Temsco Helicopters (tel. 866/683-2900 or 907/983-2900; www.temscoair.com) takes 80-minute tours near Skagway, with half that time spent on a glacier (not in Glacier Bay); those flights cost $289. A 90-minute helicopter and dog-sled tour, including an hour at a dog camp on Denver Glacier, is $479.
A Skagway Trail Map is available from the visitor center, listing 10 hikes around Skagway. An easy evening walk starts at the footbridge at the west end of the airport parking lot, crossing the Skagway River to Yakutania Point Park, where pine trees grow from cracks in the rounded granite of the shoreline. Across the park is a shortcut, taking a couple of miles off the trip to Dyea and to the Skyline Trail and A.B. Mountain, a strenuous climb to a 5,000-foot summit with great views. On the southeast side of town, across the railroad tracks, a network of trails heads up from Spring Street between 3rd and 4th avenues to a series of mountain lakes, the closest of which is Lower Dewey Lake, less than a mile up the trail.