The first time I visited Seattle, I made the huge mistake of skimming over Pioneer Square. So, when I got the chance to explore more of Seattle’s “first neighborhood” on my second trip, I took it. And this historic district didn’t disappoint.
I’ll admit that between my first whirlwind visit and my second, I’d heard mixed things. I knew I’d learn plenty about the city’s history and see some beautiful architecture. But I’d also heard the neighborhood had seen better days.
What I discovered on my visit to Pioneer Square, though, was more complicated and more interesting than either the tourism brochures or the TripAdvisor and Reddit horror stories suggested.
If you’re trying to figure out whether Pioneer Square deserves a spot on your Seattle trip itinerary, my honest answer is yes. But how you spend your time there matters a lot.
Here’s exactly what I’d do to fill out a day in Pioneer Square…
Start your morning at Pioneer Square Park
With a free day to explore, I’d start my day at the neighborhood’s namesake, Pioneer Square, at the corner of 1st Avenue and Yesler Way.
This square marks where Seattle began. Standing here for a few minutes in the morning before the tourist crowds build is the perfect way to feel that history come to life.
My favorite feature at Pioneer Square is the 50-foot Tlingit totem pole that dominates the space. (On a walking tour, I learned that it’s a 1940 replica of the original 1899 installation, but it’s eye-popping nonetheless!)
Also, keep your eyes peeled for the park’s distinctive cast-iron and glass pergola. This beautiful pergola stopped me in my tracks the first time I saw it. The ironwork is extraordinarily detailed for something that was originally just a cable car shelter, designed by architect Julian F. Everett and installed in 1909.
As I explored the square, I also spotted a bust of Chief Seattle, the Suquamish and Duwamish leader the city is named after. It’s tucked into the square in a spot many visitors walk straight past.
Pioneer Square is compact enough that you won’t need more than 20 minutes here.
After getting your first historical sightseeing mission out of the way, grab a coffee before the day gets going. Caffé D’arte (99 Yesler Wy) is right across the street. Besides some of the tastiest coffee I tried in the area, the cafe also serves delicious breakfast like ham and cheese croissants and quiche.
Wander around Occidental Square
From Pioneer Square Park, it’s a short two-minute walk south along 1st Avenue to Occidental Square. I’d carve out at least 10 minutes to wander around this historic city square. With its greenery climbing up the historic buildings, it’s one of my favorite spots in the neighborhood.
What I love most about Occidental Square is how much is packed into such a small space. The totem poles carved by Duane Pasco are stunning up close. I was also stopped in my tracks by the Fallen Firefighters Memorial by Hai Ying Wu. This bronze sculpture pays tribute to four local firefighters who died fighting a fire in the neighboring Seattle Chinatown-International District.
In the warmer months, Occidental Square really comes alive. On my visit, I spotted a giant chessboard, foosball tables, and ping pong.
(Although I didn’t see it for myself, locals told me that food trucks rotate through the square regularly throughout the week, too.)
If you skipped on coffee around Pioneer Square, here’s your second chance! Walk across the street for coffee and pastries at the industrial-chic Lady Yum (116 S Washington St). I’d highly recommend giving their macaroons a shot; they’re to die for.
Chill out at Waterfall Garden Park
Just steps from Occidental Square, Waterfall Garden Park is easy to miss. And that’s exactly what makes it such a great find!
The park sits behind a gate on 2nd Avenue with small, easy-to-miss entrances on both 2nd Avenue and South Main Street. I stumbled onto it almost by accident, and it immediately became one of my favorite hidden gems in Pioneer Square.
The centerpiece is a 22-foot artificial waterfall set on the grounds of what was once the first UPS headquarters. Stepping inside feels like discovering a secret garden in the middle of the city. The sound of the water and the surrounding greenery make it genuinely relaxing after a morning of sightseeing.
It’s worth noting that Waterfall Garden Park is only open from 8 am to 5:45 pm daily. Make sure you time your visit accordingly.
Learn about Seattle’s gold rush history at Klondike Gold Rush National Historical Park
From Waterfall Garden Park, it’s a short 2-minute walk south to the Klondike Gold Rush National Historical Park. Don’t let the name fool you: This “park” is actually a free museum housed in the former Cadillac Hotel. And it’s one of the most underrated stops in Pioneer Square.
I was surprised by how engaging this museum was. Park rangers walk you through Seattle’s role in the 1897 gold rush across two floors of interactive exhibits. You can also enjoy short films and a chance to pan for gold.
If you’re visiting with kids, they can earn a Junior Klondike Gold Rush badge to bring home. (A pretty cool souvenir if you ask me!)
One tip I’d pass on: Ask for the Trail to Treasure map at the visitor center. It outlines a self-guided walking tour of Pioneer Square’s main historical attractions. I found it really useful for orienting myself around the neighborhood.
Budget around an hour at the Klondike Gold Rush National Historical Park, and don’t rush it. Admission to the park is free, so there’s no reason to skip it.
See the city’s foundations on Bill Speidel’s Underground Tour
From the Klondike Gold Rush National Historical Park, it’s a 7-minute walk north along S Jackson St and 1st Avenue to Bill Speidel’s Underground Tour. This is one stop in Pioneer Square I’d call non-negotiable, especially if you’re a history buff.
Bill Speidel’s Underground Tour takes you beneath the streets of the Pioneer Square neighborhood into the brick-lined tunnels of pre-fire Seattle, giving you a look at the city before the Great Fire of 1889.
What surprised me most about the tour was how entertaining the guides made it. They inject plenty of humor into the history, which keeps things moving at a pace that never feels like a lecture.
After the tour, it’s worth browsing the exhibits at the Rogues Gallery and poking around the Underground Gift Shop. History buffs should look out for a copy of Sons of the Profit by Bill Speidel. It’s a great way to bring the history lesson home.
Tours run daily on the hour from 9 am to 7 pm between April and September, and from 10 am to 6 pm between October and March. I’d recommend booking your tickets in advance online to avoid showing up and missing your preferred time slot.
Marvel at the city from above at Smith Tower
From Bill Speidel’s Underground Tour, it’s a short 2-minute walk north along 1st Avenue to Smith Tower. Dating back to 1914, this was Seattle’s first skyscraper. And while I was more enchanted by the views from the nearby Sky View Observatory, Smith Tower is still, in my opinion, one of the most underrated stops in the whole neighborhood.
I’d recommend buying your observatory tickets online in advance for $15 rather than at the desk. Before heading up, take a few minutes with the exhibits in the lobby about the building’s history.
The vintage Otis elevators alone are worth a look. On the way up, the elevator operator is more than happy to deliver some fun facts about the building if you’re in the mood to chat.
The highlight of any visit to Smith Tower is ascending to the open-air observation deck on the 35th floor. The views over the Seattle skyline from up here are spectacular.
(At the time I visited, it was the city’s only open-air observation deck. In 2018, the Space Needle also added an open-air section with its Spacelift addition.)
My recommendation is to time your visit to Smith Tower for late afternoon. The Observatory Bar on the 35th floor is a speakeasy-style bar serving exclusive Smith Tower barrel-aged liquors, local craft beers, and signature cocktails.
It’s first-come, first-served with no reservations, so arrive early. On busy weekend evenings, the wait can stretch to 30 minutes or more. But sitting up there as the sun drops below Puget Sound is one of the best experiences I’ve had while visiting Seattle.
Enjoy PNW-inspired dinner & drinks around the neighborhood
Although, as an Asian food fanatic, I found the restaurants around the nearby Seattle Chinatown-International District more to my tastes, I still found some great bites around Pioneer Square worth seeking out.
For dinner, my two top picks in the area are Taylor Shellfish Oyster Bar (410 Occidental Ave S) and Damn the Weather (116 1st Ave S).
Taylor Shellfish is the more classic Pioneer Square experience. The oysters here are some of the freshest I came across in Seattle, the Bloody Marys are award-winning, and the historic space earns its reputation. For non-oyster fans, the shrimp po’boy and Dungeness Crab roll are both excellent alternatives here, too.
If you’re after something more adventurous, Damn the Weather is a gastropub that leans into experimental dishes like Duck Fat Fries, fried fava beans with seaweed, and a fettuccine dish with morels and grape-leaf pesto. It’s better suited for an adventurous crowd, but I loved its unique menu.
For drinks, Pioneer Square punches well above its weight. Flatstick Pub (240 2nd Ave S) is a great early evening option with Seattle-themed mini golf, including a replica Space Needle, arcade games, and a solid selection of beers and nachos. It’s exactly as fun as it sounds.
For cocktails, the Good Bar (240 2nd Ave S) has a serious list of mixed drinks and Spanish gin and tonics, with Middle Eastern bar snacks to keep you going. Happy hour runs Tuesday through Saturday from 3 pm to 6 pm.
And if you want to end the night somewhere with genuine history, Central Saloon (207 1st Ave S) is Seattle’s oldest bar, dating back to 1892. It’s got exposed brick walls, live music most nights, and a stage where Nirvana reportedly played their first big city gig before signing with Sub Pop Records.
As someone who grew up with grunge on constant rotation on my Discman (yeah, I’m getting old), I couldn’t think of a better way to end a night in Pioneer Square!
