Skagway is the oldest and first incorporated city in Alaska. During the Gold Rush of 1897-98 thousands of hopeful gold seekers left Seattle and landed in Dyea and Skagway on their quest to the gold fields of Dawson (430 miles north by road). Because of the hardships of traveling over the Chilkoot and the White Pass, or Trail of '98, a group of investors and railroad builders decided to build a railroad to Whitehorse. They built the White Pass & Yukon Route Railroad in record time and completed it in 1900, too late for the gold rush which had moved onto Nome, but it ran as the main transportation from Skagway to Whitehorse for 82 years. Although closed for 5 years, it reopened in 1987 and has steadily increased its ridership ever since. White Pass recently retrieved a 100 year old steam engine that had been visiting down south for many years. Now the two old steam engines compete for attention blowing their steam whistles on busy days to the delight of the tourists. Dozens of other WP&YR diesel engines pull antique and replica train cars up to the pass each day to view waterfalls, wildlife and spectacular scenery. There are also many other tour companies that take visitors by bus up the same valley, but on the other side to destinations in British Columbia and Yukon.

Most people who step off the cruise ships in the summer are amazed at how cute Skagway is. While resembling a Hollywood set, it is the real thing - many of the buildings are over 100 years old and lovingly restored by owners and by the National Park Service. The entire downtown area is a National Historical Landmark of Klondike Gold Rush NHP. Many of the buildings are owned by the Park and leased back to businesses who sell everything from children's clothes, books, diamonds and gold. The leases bring money back into the community in the form of wages to painters, carpenters and ranger-interpreters who give free walking tours and movies at the visitor center each day in the summer. A replica saloon and refurbished homestead are also part of the park. The city of Skagway maintains a year-round visitor center in the Arctic Brotherhood Hall downtown and a summer-only museum on 7th in the city hall building.

For those people not wanting to ride a bus, helicopter, boat or train, there are also  horse-drawn carriages to local attractions. In addition, the city produces both a local walking tour map and hiking guide of the local trails. Both are available at the visitor center when you arrive. Dyea, the community a few miles west is the local "Alaskan" place to picnic and view wildlife. Although you can walk there, most rent a car or take a taxi or shuttle out. Locals also love to go blueberry picking in August and September, but keep their special spots secret. In the summer there is one bus company that transports from Skagway to Whitehorse ($60 one way), but none in spring, fall or winter. There are car rentals at the airport in Whitehorse, and spectacular views on the Klondike Highway. Two small airlines serve Skagway year-round: Wings of Alaska and Air Excursions.