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Travel Guide: Skagway, Alaska

Skagway means “the windy place” in the native Tlingit language.  It was also known as the “Gateway to the Klondike” during the Gold Rush in the late 1800s.  The small town is full of history and fun things to do!

Check out our travel guide and join us on the Denali Dream, Caribou Crawler or Alaska Expedition to travel here on the adventure coach!


Take a train ride on the White Pass Railroad.  The White Pass Train chugs along a breathtaking route through the wilderness. Learn all about the search for an alternate route to the grueling Chilkoot Trail, which was the original route into the Yukon Territory for men seeking storied riches.

National Park Service Walking Tour (free!): At the NPS building on the corner of 2nd Ave. & Broadway, you can sign up for a 1-hour walking tour to learn about Skagway’s remarkable history.

Ghosts & Goodtime Girls Walking Tour: The Red Onion Saloon offers rather entertaining walking tours through Skagway, guided by hilarious madams detailing stories of history and haunts! Not a G-rated tour!
You can also opt for the Brothel Tour (on the hour after 10 a.m.) inside the Saloon.  

Ocean Raft Alaska: This high-speed rafting adventure in a super cool orange jumpsuit rivals a theme park’s best roller coaster. The boat captains are super knowledgable and fun. This is a $150 well spent (don’t forget to tip your guide!).

M&M Tours/Skagway Tours: You’ll see these kiosks around town and they sell excursions. There’s probably something like a million things to choose from. 😉 Guided hiking or kayaking, glacier tours, helicopter rides, dog mushing, horseback riding, zip-lining and rock climbing tours can be purchased here.  If you’re a zip-lining fanatic, opt for the Grizzly Falls with AlaskaX!

Be forewarned, most tours are expensive. Another good tip is to find out what company is actually doing the tours and book directly through them. 

There is an M&M booth on Broadway before 1st Ave. (left at NPS building) or Skagway Tours at 5th & Broadway.


Hitting the trail is our favorite thing to do during a visit to Skagway.

Dewey Lakes Trail System (moderate to difficult): Take the trail up to Lower Dewey Lake (0.9 miles round trip/1-2 hours).  The switchbacks to get up there are steep, but once you’re at the lake, the trail flattens out.  You can take the loop around the lake (3.6 miles round trip, 2-3 hours), but be aware that the trail narrows and there’s some scrambling on the other side.

You can also take a left at the lake loop trail head and head for Icy Lake Trail.  The lake is absolutely gorgeous, but it’s a pretty steep hike up (6 miles round trip/3-4 hours). Alternatively, head in the opposite direction to Sturgill’s Landing and take in the sweeping views of the Lynn Canal.

From this trail system, you can reach Upper Dewey Lake (strenuous, 6 miles roundtrip) after climbing just over 3,000 ft. Seeing the striking blue color of this alpine lake is worth every sore muscle! Strong hikers will love to continue another two miles to Devil’s Punchbowl.

Yakutania Point (easy): Once you’ve passed over Broadway on 2nd Ave., keep walking until the road dead ends.  Go left and follow the sidewalk until you see the airport (possibly the smallest one you’ll ever see).  Through the airport parking lot and over the footbridge, the Yakutania Point trail is an easy stroll through the woods (elev. gain of 20 ft.).  You can take the trail to the first picnic area or continue on to see Smugglers Cove (2 miles round trip).  There are signs the whole way. 

A.B. Mountain (difficult): This 10-mile roundtrip hike gains about 5,000 ft. in elevation. Expect to have an all-day adventure with unparalleled rewards.

Take the shuttle ($2-$5) to the Lower Reid Falls trail.  This is an easy hike that strolls through the spooky Gold Rush Cemetery to a beautiful waterfall at the end of town.


Red Onion Saloon: 2nd & Broadway – Pizza, salads and brews – $$

Glacial Smoothies: Left of Broadway on 3rd Ave. (on the right) – Delicious smoothies and breakfast & lunch options.  Try the Super Bagel for breakfast (everything bagel w/ cream cheese, bacon and basil) or the Butternut Squash Wrap for lunch! You don’t have to, but you won’t be disappointed! – $

The Bonanza Bar & Grill: Between 3rd & 4th Ave. on Broadway – The food here is pub fare. Have an Alaskan beer and play some pool or a board game in the back room. – $$

Skagway Brewing Company: On 4th Ave. between Broadway & Spring St. – By far, in our opinion, the tastiest food served in town.  Fish & Chips or a burger are the way to go.  Go after 6 p.m. for specialty burgers.  They have some delightful vegetarian options, too (the falafel pita..mmm)!  This is also an awesome brewery.  The Spruce Tip Ale is delicious if it’s not sold out! Try the draft sampler if you’re a beer lover.  – $$

The Pizza Station: 4th Ave. & State Street (one block over from Broadway) – So, this is your late night stop to experience the locals favorite dive bar.  There’s pool and bar food. The Cheesy Bread is the way to go if you want a cheap pizza option (you can add whatever toppings you want and it’s big enough to share!).  Most people like to take a photo with the Morning Wood Hotel sign, which is located above the bar. – $$

$$ – Everything is more expensive in Alaska.  The entrees will generally cost anywhere from $12-$20.

And of course, in Tortoise fashion, you could head to the IGA grocery store on 4th & State Street to pick up all of the ingredients for a packed lunch to bring up to Lower Dewey Lake!


Westmark Inn in Skagway


Pullen Creek Tent Camping

(907) 983-2768

Morning Wood Hotel 

(907) 983-2200

Mile Zero Bed & Breakfast 

(907) 983-3045

There are free camping spots at Lower Dewey Lake.  Once you’re up there, you can’t miss ‘em!

Just nine miles into the wilderness outside of Skagway, you can camp at the Dyea Campground along the Taiya River.