Skagway Alaska train with snow-capped mountains in background
Photo Credit: Ronald Wong

A Local's Guide to Skagway

A Local's Guide to Skagway

Olivia Klupar is an Alaska entrepreneur. Born and raised in Skagway, Olivia grew up working in the family hospitality businesses and sharing her home with visitors. Passionate about all things Alaska, in 2014, Olivia and her brother, Greg, founded what is today called Voyij, Alaska’s online e-commerce destination for quality, local gifts and experiences from Alaska’s incredible small business community. Working hand-in-hand with hundreds of local artists and small business owners to represent and sell their works online, Voyij offers the largest collection of Alaska’s finest gifts, rare collectibles, fresh seafood, and must-book activities from small businesses you just can’t find anywhere else.

I consider myself the luckiest person in the world to be able to call Skagway my home. Our town is small, four blocks wide by 23 blocks long and you can’t go anywhere without stopping to say "hi" to someone you know, whether at the post office, the hardware store, or just walking down the boardwalk.

We live in a national park, with dozens of hikes within a five-minute walk out our front door. Tucked away in a valley with mountains on three sides and the Lynn Canal to the south, we are completely isolated with neighboring Whitehorse, Canada, a two-hour drive north and Haines, a 30-minute boat ride south. There are numerous peaks that take you from sea level to 3,000+ feet with views down the canal (on clear days you can see Mount Fairweather in the distance), hanging glaciers (Harding Glacier is the most notable overlooking Skagway), and the general beauty of our natural surroundings. Skagway is at the intersection of the coastal Tongass National Forest, higher elevation alpine tundra, and interior boreal forest, where lichen and moss, mushrooms, ancient old growth forests, spruce tips, devil’s club, wild blueberries, high-bush cranberries, and fireweed grow freely.

Skagway played a vital role during the Klondike Gold Rush of 1898 as a transportation portal for the White Pass & Yukon Route railway and the Chilkoot Trail. The city commemorates its gold rush past with board-walked streets and turn-of-the-century architecture including several museums and visitor centers. It’s like stepping back in history.

Day Hikes

On sunny summer days, there is nothing better than to get out of town and go for a hike. Skagway is a hiker’s paradise, with something for everyone. Upper Lake is a 1.5-2-hour uphill climb to a remote lake (bring a towel so you can jump in on a hot day!). My perfect afternoon is sunbathing by the lake, listening to the marmots on the nearby hillside, and going for a dip in the ice-cold lake. This area is also a great jumping off point – literally – for paragliders. The clear water stream on the way up is clean so you can fill your water bottle with glacier water. You can continue on to Devil’s Punchbowl for a beautiful view of Skagway and the canal. AB is another full day hike. A 6-to-8-hour, roundtrip hike (longer if you stop to eat the wild blueberries!), this hike gets you quickly above the tree line and you can hike for miles along the ridge line, with a picturesque 360-view of Lynn Canal, the Dyea flats, and the mountains and glaciers to the north in the Yukon. For the more adventurous, take the White Pass & Yukon Route train out to Laughton Glacier, a hike that leads you right up to the glacier itself or venture into the Yukon with too many climbable peaks, many without names.

Scenic views in Skagway
Scenic views in Skagway

Chilkoot Trail

The Chilkoot Trail is the most famous Skagway hike, a 33-mile, 3-to-5-day trip with a major highlight: an intense day climb up the “golden staircase” into the wide-open expanse of the Canadian Yukon. This trail is the historical trail 100,000 gold miners took to get to the gold fields of Dawson City, Canada, in what is today known as the Klondike Gold Rush of 1898. This hike starts in Skagway’s sister city and now-ghost-town Dyea, and offers the best of Alaska/Yukon hiking within the wet, mossy Tongass National Forest and boasting striking views of glaciers and on the Alaska side opening up to the stunning landscape, lakes, and sandy beaches on the Canadian side. It is possible to run this trail in one day if you leave on summer solstice and carry a light pack.

Spend time in Skagway

While Skagway may be small and isolated, we have events throughout the year that draw a fun crowd. If you are into cross country skiing, join us for the Buckwheat Ski Classic, held in March each year across the border at Log Cabin, a favorite local spot for snowshoeing, cross country, and backcountry skiing. Our solstice celebration and Fourth of July events are quite celebratory with Alaskans and Canadians enjoying the parade, the world’s largest egg toss, and parties well into the evening (my favorite hangout is Olivia’s Bistro with our garden view and fresh mint mojitos). September draws an international crowd for our well-known Klondike International Road Relay, a 10-leg, 100-mile relay through the night, starting in Skagway and ending in Whitehorse, Canada, with many runners sporting fun costumes!

Brewery in Skagway
Brews with a view in Skagway. Photo Credit: @thesocialblondexo

View the stars

One of the best parts about living in Skagway is that there is no light pollution so the sky on a clear night is miraculous. On dark, clear nights, I love grabbing a blanket and viewing the stars, with the Big Dipper right overhead and if we’re lucky, the Milky Way galaxy is also visible. In August, we get the Perseids meteor shower and by September, the northern lights can also be seen with its magical dancing display.

Learn more about Skagway >>


Alaska: AKA Your Next Adventure

Where will your Alaska adventure take you? Order our Official State of Alaska Vacation Planner and plot your course.