I'm Sharon, your ApartmentHomeLiving.com Local Expert for Seattle, Washington. I've lived here for 30+ years and have watched the city grow while holding onto what makes it unique. It's my pleasure to share some history and insider information about my hometown with you. For this guide, we'll stick close to Downtown, with one exception, Alki, in West Seattle.

Welcome to the Emerald City

Seattle's nickname, The Emerald City, is fitting. Rain keeps everything lush and green. You'll find moss-covered forests, even in January, and the evergreens hold their color year-round. Seattleites know the rain is a blessing. We don’t wait for sunshine to get outside. And, when the sun is shining, it's downright magical. We usually dress in layers. A rain jacket or hoodie is optional, but if you use an umbrella, we'll know you're not from around here.

Seattle sits between Puget Sound and the Cascade and Olympic mountains, where nature can be as challenging as it is beautiful. Early on, settlers had to shape the land and build around obstacles to make the city work. It took a lot of adaptation to get our beloved Emerald City to the level it is today.

First Landing

Pioneers first landed on the other side of Elliot Bay, on Alki Point. Arthur Denny guided the move west, and his brother David helped scout the area before the main group arrived. Arthur later recorded their experiences in his memoir, Pioneer Days on Puget Sound. They named their settlement New York Alki. New York, in honor of the booming East Coast city. Alki was a Chinook word, meaning someday.

To become another New York, someday. That was the dream.

However, the shoreline at Alki Point was shallow and exposed, which meant ships had to anchor too far from shore to make trade manageable. The Duwamish River emptied into Elliott Bay on the eastern side. That area (today’s Pioneer Square and downtown Seattle) offered deeper water for ships, a more sheltered harbor, and easier access to timber and fresh water. It's no surprise that the settlers soon moved to the east side.

A Swampy Mess

They named the new settlement after Chief Sealth (AKA Seattle), who had played a key role in welcoming and guiding the newcomers. His people, the Suquamish and Duwamish tribes, had lived in the region for generations. Still, no amount of goodwill could change the fact that we built Seattle on an unstable patch of shoreline that was prone to flooding. Streets were little more than dirt paths. Continuous rain made the whole place a swampy mess. Despite the mud, the town thrived on lumber. Loggers skidded giant firs down Mill Street, which is now Yesler Way, heading to Henry Yesler’s sawmill on the waterfront.

That timber chute gave the world a new phrase: Skid Road, which came to mean the rougher part of town.

Seattle’s Skid Road drew a hard line in the muck. Homes, churches, and respectable businesses were on the north side of Yesler Way, and to the south, you would find brothels, gambling dens, and saloons. Eventually, Seattle became a boomtown with a drainage problem. Not only that, but all the wooden buildings crammed onto unstable ground set the stage for the Great Seattle Fire of 1889. When it hit, the city burned fast.

The fire wiped out 25 blocks in an afternoon. It also gave Seattle a chance to start fresh.

Pioneer Square: Seattle’s First Playground

Seattle raised its streets one story higher and addressed the plumbing issues. The new street level left deserted passageways and storefronts, now known as the Seattle Underground. Wander the alleys downtown and you’ll spot bricked-up doors, purple glass skylights in the sidewalks, and stairways that go nowhere. These are leftovers, where old Seattle still has a foot in the present.

You can't consider yourself a local until you've taken one of Seattle's Underground tours. The oldest and most popular tour is Bill Speidel's Underground Tour. Speidel's tour starts at Doc Maynard's Public House, the saloon named after David “Doc” Maynard, one of Seattle's original settlers. Doc Maynard’s Magnificent Front Street Band supplied the music. Over the years, hundreds of bands have played there.

I like to travel on foot or by bus when I'm downtown. It's just easier to get around, and you don't have to pay for parking. From Pioneer Square, you’re within a 15–20-minute walk to most of downtown. Or you can use the metro.

The Gateway to Alaska

After the fire, Pioneer Square remained the center of the city. During the Klondike Gold Rush, when Seattle became known as the Gateway to Alaska, Pioneer Square was where to find equipment, ships, saloons, and hotels. These days, insiders know where the original Pioneer Square saloons are still pouring drinks. The Merchant's Cafe and Saloon is the oldest bar in Seattle, established in 1890. It might also be the most haunted. It was featured on the TV show, The Dead Files. Apparently, a ghost named Otto, who had managed the place n the early 1900s, decided to stick around. And he's not the only one haunting the establishment, according to the owner and several employees and customers. I wouldn't want to go into that basement alone.

As an artist living at the OK Hotel in Pioneer Square, I spent some time in the early 2000s painting with fellow Seattle artists during live music events at the Central Saloon and J&M Café. Sadly, the J&M closed in 2019, and it doesn't appear to be opening again, anytime soon. But the Central Saloon, which was part of the rebuild after the Great Fire of 1889, is still going strong. Before the fire, it was The Watson Bros. Famous Restaurant. Afterward, the new owners named it The Seattle Bar, which became the Central Café in 1919 and eventually transformed into the Central Saloon.

From Grunge to Galleries

When I moved downtown in the early 2000s, I was delighted to find out that Seattle was the birthplace of grunge in the 1980s. The Central Saloon, J&M, and the OK Hotel are where it happened. Some of my favorite bands, like Nirvana, Soundgarden, and Alice in Chains, among many others, played at these historic Pioneer Square venues in the 1980s.

The O.K. Hotel went up in 1914 on what was then Railroad Avenue S (today’s Alaskan Way S). It was in a rough part of town facing Elliott Bay. The OK catered to sailors, dockworkers, and lumberjacks, and they were all ready and willing to drink away their paychecks on Skid Road. By 1953, the Alaska Way Viaduct added noise, soot, and overshadowed the OK. The hotel got a revival in 1988 as a live music venue.

After the 6.8 magnitude earthquake that damaged the building's structure in 2001, the OK Hotel was renovated into artist studios and apartments. I lucked into a studio space right next to what used to be the dance floor and opened my art studio to the public during Pioneer Square's first Thursday Art Walks.

Pioneer Square's First Thursday Art Walk began in the 1980s with a group of gallery owners who collaborated to create a map of local galleries and feature a monthly art walk. It was the first in the country. Insiders enjoy visiting local artist studios as much as the more refined galleries. In addition to the OK Hotel, the Tishiro Kaplan building is a vibrant artist community.

Go To The Market

Just up the hill is a Seattle icon, the Pike Place Market. When Seattle rebuilt after the Great Fire, downtown quickly became a hub for trade. In 1907, city officials opened a public market where farmers could sell directly to customers. It became the Pike Place Market. You’ll recognize the iconic Public Market Center sign with its neon clock and the brass piggy bank, Rachel the Pig, who has been collecting donations for social services since 1986.

My kids and I loved to explore the Market’s below street level antique shops, comic stands, and the Magic Shop was always a hit. For food, grab a hot Piroshky at Piroshky Bakery, and watch fresh curds being made at Beecher’s Handmade Cheese. Or sip oysters at The Athenian, a market restaurant dating back to 1909 with some of my favorite bay views.

And don’t miss a gift from the 1990s, Post Alley’s infamous Gum Wall. This quirky landmark is kind of gross, but its popularity has continued to stick.

Overlook Walk

I remember the original Alaskan Way Viaduct. The drive overlooking Elliot Bay was spectacular. Sadly, the 2001 Nisqually earthquake damaged it. By 2009, officials agreed to replace it by boring a two-mile-long tunnel under the city’s waterfront.

The whole thing was fairly controversial, but the results opened up the waterfront downtown, making it accessible. Now, where the Viaduct used to be, Overlook Walk is an elevated pathway (and elevator) from Pike Place Market to the waterfront and 20 acres along the waterfront. I haven't had a chance to see it yet, but my friends say the views of Elliott Bay, Mount Rainier, and the Olympic Mountains are incredible. Make sure to plan a ride on Seattle's Great Wheel while you're there.

Back to Alki: Where It All Began

Circling back across Elliott Bay to where it all started, Alki Point. Today, Alki Beach is a long strip of sand with views of downtown’s skyline and the Olympics in the distance. You’ll dock at Seacrest Park in West Seattle, where the paved waterfront trail winds along Alki Beach. In summer, you can even bring your bike aboard and ride the whole shoreline.

The settlers called it New York Alki. New York, someday, dreaming of a city that could rival the East Coast. The someday part came true, though not in the way they imagined. Pioneer Square became the city’s commercial heart, and Alki Beach, a place to relax.