A good place to start is the Gold Rush National Historical Park Visitor Center, on the water side of downtown in the White Pass and Yukon Route Railroad station. It gives a great overview of the Gold Rush saga, as well as being in the train station for the WP&YR RR, which is fascinating just by itself. The town of Skagway also operates its own visitor’s center, in the restored and very dramatic Arctic Brotherhood Hall, with its 10,000 or so nailed on pieces of driftwood, probably the most distinctive building in all of Alaska. The Fraternal Order of the Arctic Brotherhood constructed this hall and at least another in the Yukon Territories as a social and cultural organization to further the interests of the miners. It grew to have substantial political muscle as well. being an early advocate for more political power for Alaskans to manage their own affairs locally rather than through Washington, DC.
Pick up a copy of the walking tour map at the AB Hall. It’s got directions up to the Gold Rush Cemetery, the Trail of ‘98 Museum, and other points of interest. It’s definitely worthwhile to walk around with the map as your guide. The hike to Lower Dewey Lake (3 hrs. RT) has a steep stretch at the beginning, but then flattens out for a very pleasant walk.
Of course, Skagway’s signature hike is up the old Chilkoot Trail, followed by so many of the men of ‘98. This is way, way more than a pleasant stroll; more like a grueling 4-5 day epic, and that’s in summer, not in the depth of winter with the poorly insulated clothing of the day and 1,000 pounds of gear to pack over the summit. If you start up the trail, think about this: many of the men who took it made a dozen or more trips back and forth to ferry their loads if they couldn’t afford to hire a native porter to help them.