Alaska earned the nickname “The Last Frontier” for its vast wilderness, remote towns, and untouched landscapes. Skagway is one of the few places where you can still see that frontier spirit up close.
With dramatic scenery, gold rush-era buildings, and trails once traveled by fortune seekers, it offers breathtaking train rides, epic hikes, and a glimpse into a wilder chapter of American history. It’s a favorite stop for cruise ships and one of my highly recommended places to go in Alaska.
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Get to Know Skagway, Alaska’s Last Frontier town
Skagway is small, scenic, a little wild, and packed with more history and heart than you’d expect from a town with less than 1,000 year-round residents. From jaw-dropping train rides and glacier landings to Victorian brothels and beer brewed right in town, Skagway brings a mix of outdoor adventure and quirky charm that’s hard to beat.
I’ve visited a many times, and every time, I leave already plotting my return. One of my favorite memories is showing up in the dead of winter for the annual Buckwheat Ski Classic. I wasn’t brave enough to strap on skis myself, but cheering on the racers and soaking in the small-town energy was something special! There were costumes, antics, and enough mulled wine to keep things interesting.
Skagway is also a top stop for Alaskan cruise ships, which means that for a few hours a day, the town can be buzzing with travelers. But don’t let that fool you! Step just a few blocks off Broadway or stay overnight, and you’ll get to know the real Skagway. It’s steeped in Klondike Gold Rush history, surrounded by mind-blowing scenery, and bursting with outdoor adventures that go way beyond the cruise crowd.
If you’re planning a trip through southeast Alaska by ship, plane, or scenic road trip from the Yukon, don’t skip Skagway! And if you’re wondering what to do once you get here, keep reading. I’ve rounded up my favorite hikes, hidden gems, historical spots, food finds, and a few can’t-miss tours you’ll want to book in advance.
Just follow the sound of the CHOO CHOO. You’ll hear it enough times in a day!
Skagway’s History: Tlingit Roots, Gold Rush Dreams, and the Railroad That Saved the Town
Long before prospectors arrived in search of gold, the area now known as Skagway was home to the Tlingit people. The name “Skagway” comes from the Tlingit word Skagua, meaning “place where the north wind blows.” Local legend tells of Kanagoo, a powerful woman-turned-stone figure who caused the fierce winds that sweep through the Taiya Inlet.
Everything changed in 1897, when gold was discovered in the Klondike region of the Yukon. Skagway became the gateway north, a lawless boomtown packed with stampeders chasing fortune. At its peak, the town had saloons, brothels, gambling halls, and one of the most infamous con artists on the frontier: Jefferson “Soapy” Smith. His reign was short-lived, ending in a gunfight on the wharf, but the stories still echo through town.
Not everyone came to take advantage, though. One early settler, Captain William “Billy” Moore, believed the area had long-term promise. He built a log cabin, a sawmill, and a dock in anticipation of what was coming. You can still visit his original homestead today, part of the Klondike Gold Rush National Historical Park.
After the rush faded, it was the White Pass & Yukon Route Railroad that kept Skagway alive. Built against the odds through steep mountain passes, it became a lifeline to the Yukon and a marvel of engineering. Today, it’s one of the most popular ways to experience the region’s history and scenery, and still departs from the center of town.
Skagway may be small, but its past is larger than life. You don’t need to look far to find it: it’s in the wooden sidewalks, restored buildings, and museum displays that line Broadway. And if you have time, the park rangers at the visitor center are a great resource for digging deeper into the town’s gold rush roots and Indigenous heritage.
How to Get to Skagway
Skagway might feel remote, but it’s surprisingly accessible. Each route has its own perks depending on your travel style and schedule. Here’s a look at your options.
Cruise Ship
Cruising remains the most common way to visit Skagway, and for many travelers, it’s one of the most scenic ports on the Inside Passage. Most major cruise lines dock right in town, just steps from Broadway. Even if you only have a day here, you can easily squeeze in a train ride, hike, or glacier tour before getting back on board. Just keep in mind that the town gets busiest when multiple ships are in port. Early mornings and evenings are often the quietest times to explore.
Floatplane
Flying into Skagway by floatplane is one of the most unforgettable ways to arrive. I once took a 45-minute flight from Juneau with Alaska Seaplanes, and it was breathtaking! You fly over glaciers, fjords, and forested valleys before touching down in this tiny frontier town. Flights typically run year-round, but weather can cause delays, especially in spring and fall. Go for this option if you’re short on time and want a bird’s-eye view of Southeast Alaska.
Ferry
If you’d rather stay on the water, Alaska Fjordlines operates high-speed catamaran service between Skagway, Haines, and Juneau during the summer season. The trip is scenic, relaxing, and gives you a chance to watch for whales, sea lions, and bald eagles along the way. This family-run company has been around for years and remains a great alternative to air travel. There’s also the Alaska Marine Highway System, which offers ferry service throughout Southeast Alaska, including Skagway, although schedules are more limited.
Car or RV via the Klondike Highway
Skagway is connected to the Yukon and the rest of North America via the South Klondike Highway. If you’re road-tripping through Canada or exploring the Yukon, it’s entirely possible to drive into town. Skagway is about 110 miles from Whitehorse and just under 100 miles from the Alaska Highway. The drive is stunning with mountain passes, turquoise lakes, and wide-open skies.
If you plan to cross the border by car, don’t forget your passport. U.S. and Canadian customs are both located just outside of town, and crossing times can vary depending on traffic. If you’re in an RV, plan ahead for fuel and grocery stops, as services between Whitehorse and Skagway can be sparse.
Top Things To Do in Skagway
Skagway packs so much with character, history, and natural beauty for such a tiny town. Whether you’re here for a quick cruise stop or staying for a few days, there’s much more to explore beyond the usual walking tour of Broadway. Here are some of my favorite things to do, plus a few worth planning ahead for.
Scenic Tours & Glaciers
Take a Glacier Discovery Flight
For a true once-in-a-lifetime view of Alaska’s icefields, book a flightseeing tour with Temsco Helicopters. These 40-minute trips lift you over the jagged peaks of the Coast Mountains before landing on Meade Glacier, where you can walk on the ice and soak up panoramic views. Some tours even include summer dog sledding. Yes, real huskies pulling a sled on snow, even in July!
It’s not cheap, but it’s one of the most memorable splurges you can make in Alaska. Flights depart near town and run daily during cruise season. Spots fill quickly, so book ahead if this is on your list.
Paddle Through Wilderness on Chilkoot Lake
If you prefer to stay closer to the water, the Chilkoot Lake Wilderness and Wildlife Tour offers a slower and more serene look at Alaska’s wild side. These guided trips launch in nearby Haines and typically include a scenic ferry or fast boat ride from Skagway.
Once you’re out on the lake, you’ll paddle beneath mountain peaks, alongside forested shores, and if you’re lucky, past bald eagles, salmon, or the occasional bear!
Drive to Emerald Lake via Klondike Highway
One of the best road trips in the region starts right here in Skagway. The Klondike Highway climbs into alpine country and crosses into Canada’s Yukon Territory, passing waterfalls, rocky outcrops, and glacial valleys. The highlight is Emerald Lake, an impossibly turquoise body of water just outside Carcross.
You can rent a car and drive it yourself (don’t forget your passport) or take a guided Yukon Discovery Tour that includes stops at Carcross, the tiny Carcross Desert, and a few lesser-known pullouts along the way.
Outdoor Adventures
Hike the Historic Chilkoot Trail
This historic trail was once the main overland route to the Klondike goldfields, and today it remains one of the most iconic hikes in Alaska. Most people tackle the first few miles as a day hike, starting at the trailhead just outside Dyea. The path winds through dense forest and crosses creeks, with interpretive signs explaining what early stampeders endured.
If you’re planning to hike the full 33 miles into Canada, you’ll need to register with Parks Canada, secure a permit, and bring a valid passport. It’s a challenging but rewarding backcountry trek for experienced hikers.
Stroll Out to Yakutania Point
For something shorter and beginner-friendly, try the Yakutania Point Trail close to town. Just across the Skagway River pedestrian bridge, this easy walk leads to a rocky overlook with sweeping views of Lynn Canal. It’s a great spot for watching cruise ships, photographing the coastline, or catching the sunset. You’re also likely to spot bald eagles along the way!
Cruise Along the Skagway River Trail
This flat and easy path runs parallel to the river and offers open views of the surrounding mountains. It’s great for a casual bike ride or a long walk when you just want to stretch your legs. In early summer, the trail is lined with wildflowers, and there’s always a chance of seeing wildlife near the riverbanks.
Climb to Lower Dewey Lake Trail
A short but rewarding climb above downtown leads to Lower Dewey Lake, a serene alpine lake surrounded by spruce and hemlock forest. The trail starts steep but levels out once you reach the top. It’s perfect for a quiet picnic or some solo time by the water, with the added bonus of seeing the mountains reflected on the lake’s surface.
If you’re up for more hiking, there are trails that continue on to Upper Dewey Lake and beyond, but the lower lake loop is a satisfying outing on its own.
Museums & History
Learn History at the Klondike Gold Rush Visitor Center
Run by the National Park Service and located right on Broadway, this small but rich visitor center is the best place to start if you want to understand Skagway’s past. The exhibits dive into Skagway’s gold rush history, the White Pass Trail, and the people who shaped the town. Rangers offer free walking tours in the summer, and the restored buildings nearby help bring it all to life.
Peek Inside the Red Onion Saloon Brothel Tour
Built in 1897, the Red Onion Saloon once operated as one of Skagway’s busiest bordellos or brothels. Today, it’s a bar and restaurant with a popular upstairs museum. The tour is just 20 minutes long but filled with gold rush gossip, original artifacts, and a few cheeky surprises. It’s open daily during cruise season and costs only $10 per person.
Visit the Original Moore Homestead
Before the gold rush, Captain William Moore saw potential in Skagway and built a homestead near the waterfront. His original log cabin and home still stand and are now part of the national park. The buildings are simple, but they give a real sense of what life was like here before the boom. This one isn’t a flashy stop, but it offers a more personal look at the town’s early settlers.
Wander Through Corrington’s Ivory & Museum Shop
Part museum and part gift shop, this Broadway favorite houses a small but well-curated collection of Alaskan artifacts. You’ll see ivory carvings, Indigenous tools, and gold rush memorabilia. It’s free to visit and doesn’t take long to explore, making it a great place to learn something new while browsing for souvenirs.
Online Tours to Book in Advance
Ride the White Pass & Yukon Route Railway
This narrow-gauge railway was blasted into the mountains in 1898 and still runs today, climbing nearly 3,000 feet over 20 miles of tunnels, trestles, and switchbacks. The Summit Excursion is the classic route, taking about 2.5 to 3 hours round-trip from downtown.
Trains run daily from May through September, and advance reservations are strongly recommended when ships are in port. Pro tip: Sit on the left side heading up!
Experience Dog Sledding On a Glacier
For something truly wild, combine a glacier landing with a sled dog ride on snow. Even in July, these glacier tours operate above the tree line where snow lingers. Operators like Temsco Helicopters run combo tours that let you meet the dogs, learn how they train, and ride along on a short sledding loop.
These tours are pricey, but consistently get top reviews for being fun, informative, and truly unique to Alaska. One of my favorites!
Cross into Canada On a Yukon Discovery Tour
If you want to explore beyond the U.S. border, the Yukon Discovery Tour is a full-day trip north into Canada. The route includes stops at Emerald Lake, Carcross, the Carcross Desert, and other scenic highlights. You’ll learn about the region’s geology, Indigenous history, and how life in the Yukon compares to life in Alaska. Don’t forget your passport, you’ll need it at the border.
Taste Your Way Through a Skagway Food or Brewery Tour
Skagway Brewing Company is a great place to stop on your own, but guided tours add more context to the local food and drink scene. Some walking tours combine historical stops with tastings at restaurants and breweries, offering a fun way to experience the town through its flavors. These tend to run in the afternoons and are a great option if you’ve already done your hiking or sightseeing earlier in the day.
Where to Eat and Drink in Skagway
Skagway offers a surprisingly good food scene, especially during the summer season. Here are a few spots I’ve enjoyed, along with some new favorites that consistently get high marks from locals and travelers alike.
Seafood & Sit-Down Dining
Olivia’s Alaskan Bistro
Tucked inside the Skagway Inn, Olivia’s remains one of my favorite places to eat in town. It’s cozy and always feels a little quieter than the bigger restaurants on Broadway. The halibut chowder is still a standout, but their menu changes with the seasons and often features locally foraged ingredients. This is a great option for a relaxed dinner or a midday break from walking around.
Skagway Fish Company
Located near the harbor, Skagway Fish Co. is a tried-and-true spot for fresh seafood with water views. It gets busy when cruise ships are in, but it’s worth a stop if you’re looking for king crab legs, grilled salmon, or classic fish and chips. The casual setup makes it easy to pop in between activities, and the harbor backdrop doesn’t hurt either!
Starfire
Starfire offers a unique twist in the Skagway food scene: Thai-Alaskan fusion. It’s a local favorite for a reason! Their ginger stir-fry, curries, and seafood noodle dishes are flavorful and filling, with many incorporating local fish or produce. The setting is laid-back and cozy, hidden away just far enough from the main street to feel like a secret gem.
Bonanza Bar & Grill
For something hearty and casual, Bonanza is your go-to. This spot serves up comfort food like burgers, fish tacos, and sandwiches, and it’s a solid choice if you’re craving something simple. The atmosphere is lively during the afternoon and evenings. And they’ve got a good local beer selection on tap!
Glacial Coffeehouse
While technically a coffee shop, Glacial Coffeehouse also serves breakfast burritos, wraps, and smoothies that make it a solid option for a quick sit-down meal. It’s a favorite for early risers and folks looking to refuel between hikes or tours. The staff is friendly and there’s usually a quiet corner open if you want to sit for a while.
Snacks & Cafes
Bites on Broadway
Bites on Broadway is a charming seasonal café that serves great coffee, sweet treats, and light lunches. Owned by a Nils and Skipper, a sweet-as-pie couple who moved to Skagway from Mississippi, it brings a little Southern warmth to the Alaskan frontier. They’re usually open during the main cruise season, but it’s best to check ahead if you’re visiting early or late in the summer. The pastries alone are worth the stop!
Sweet Tooth Café
This classic diner is a step back in time, with counter seating, all-day breakfast, and homemade pies. It’s a great place to fuel up before a hike or wind down after a day on the trails. The portions are generous, and the service is always friendly. It’s popular with locals, too, which is always a good sign.
The Daily Scoop
If you’re looking for a sweet treat near the train depot, come to The Daily Scoop. They serve Alaskan-made ice cream in a variety of rotating flavors, perfect for a sunny afternoon. There’s also coffee, hot chocolate, and a few grab-and-go snacks. It’s an easy stop after riding the White Pass train or walking the waterfront.
Shop Local in Skagway, Alaska
You might not expect to do much shopping in a small town, but Skagway has a surprisingly lively retail scene, especially in the summer. Broadway is lined with stores ranging from fine jewelry and art galleries to quirky souvenir shops and local crafts. Here are a few standouts worth browsing.
Find Unique Alaska Souvenirs and Handmade Gifts
One of my favorite shops in town is Taiya River Arts, a small co-op that features work from local artists. I picked up a beautiful pair of earrings here, but they also carry handmade ceramics, prints, and textiles. If you’re looking for something meaningful to bring home (something that’s not mass-produced or cruise-ship generic), this is the place.
Lynch & Kennedy Dry Goods is another must-visit. Set in a historic building, this shop leans into its gold rush aesthetic and stocks everything from old-fashioned candies to hand-poured candles, stationery, and unique Alaskan gifts.
Just down the road, Rushin’ Tailor’s Quilt Alaska sells colorful fabrics, sewing kits, and quilt patterns with Alaskan designs. Even if you’re not a quilter, it’s worth stepping inside to see the handcrafted work and browse the regional textiles.
Explore Art, Jewelry, and Local Galleries
If you’re interested in fine jewelry, you’ll find no shortage of options along Broadway. Many stores specialize in Alaskan gold, local gemstones, and Canadian diamonds. Some shops cater more to cruise ship crowds than serious collectors, so it’s worth doing your research and shopping with care.
For something more personal, Klondike Gold Rush Jewels and Jewels by Kris both have strong reputations and carry pieces made with local materials like jade and gold nugget accents. The staff is knowledgeable, and there’s no pressure to buy.
Art lovers should stop by Aurora Jewelers, which showcases locally inspired prints, carvings, and paintings. If you’re into Northwest Coast or Indigenous art, you’ll find some beautifully curated pieces here.
Travel Through Time With a Vintage Photo Shoot
This was one of the most fun activities I did solo in Skagway! There’s a vintage photography studio in town called Old Time Photos where you can dress up in full 1890s-era costumes. You’ll get to wear corsets, suspenders, and feathered hats, then take portraits in front of saloon-style backdrops.
Kimberly, who ran the shoot when I went, was incredibly kind and made the whole thing relaxed and fun! She even helped take extra shots on my phone so I could wander around and take photos outside afterward. I recommend this for a lighthearted way to connect with the town’s gold rush past and come home with a great memory.
Where to Stay in Skagway
Options for overnight stays are limited and tend to book up quickly during the cruise season. There are no big resorts or chain hotels here, but what you will find are character-filled inns, historic properties, and cozy lodges that match the spirit of the town. If you’re staying more than a day (which I highly recommend), here are a few great places to consider.
Holland America Skagway Inn
Located right off Broadway in the heart of downtown, the Holland America Skagway Inn is one of the most convenient places to stay in town. I spent a few nights here and loved being able to walk to everything. Restaurants, trails, shops, and the train depot are all nearby!
The rooms are clean and recently updated, though keep in mind there’s no air conditioning. Fans are provided, which helps on warmer days. The property also has a lovely garden courtyard and a coffee bar in the main building. A nice bonus: they offer a complimentary shuttle to and from the ferry terminal and airport.
Historic Skagway Inn
Another charming option right on Broadway is the Historic Skagway Inn, a beautifully preserved property that dates back to the gold rush era. Each room is named after a historical character! The vibe is very much turn-of-the-century: floral wallpaper, creaky floors, and a welcoming, lived-in feel. Olivia’s Alaskan Bistro is located right inside the inn, making it an especially good choice if you value good food steps from your room.
Sergeant Preston’s Lodge
For families or travelers looking for something a little more laid-back, Sergeant Preston’s Lodge offers motel-style rooms with basic amenities and easy access to everything downtown. The vibe is friendly, and the pricing tends to be more budget-friendly than other properties in town. It’s also a popular choice for road trippers coming in from the Yukon via the Klondike Highway.
Pack Train Inn
If you’re into boutique-style accommodations, the Pack Train Inn is a small and charming property with mountain views and a quiet atmosphere just a short walk from the harbor. Rooms are simple but comfortable, with thoughtful touches like blackout curtains and soft lighting. Guest reviews praise its good location, friendly staff, and relaxed vibe.
Seasonal Tips for Visiting Skagway
Skagway operates on a rhythm that follows the cruise calendar, which usually runs from early May to late September. During this window, most shops, restaurants, and tours are in full swing, and the town comes alive with energy and color. If you visit between June and August, expect long daylight hours, vibrant wildflowers, and near-daily train departures.
That said, the shoulder months, especially late May and early September, can be an excellent time to visit. The weather is still mild, but the crowds thin out, and you’ll get more breathing room in shops and on trails. Some businesses start closing down in late September, so double-check operating hours if you’re visiting toward the end of the season.
If you’re planning to drive in from the Yukon, fall colors usually peak in early to mid-September and can be absolutely stunning along the Klondike Highway. On the flip side, winter in Skagway is quiet and very local. Most businesses close, but if you happen to be in town, the annual Buckwheat Ski Classic in March brings together residents and visitors for a weekend of skiing, costumes, and small-town fun (even if you’re just there to cheer from the sidelines, like I was!).
Whatever time of year you come, my biggest tip is this: if you have the chance to stay overnight, do it! Skagway feels totally different once the cruise ships leave for the day. The streets quiet down, the light shifts over the mountains, and you’ll get a glimpse of the town the way locals see it: slow, beautiful, and full of stories.