The Pioneer Square district, directly south of Downtown, is Seattle's oldest neighborhood. It attracts visitors for elegantly renovated (or in some cases replica) turn-of-the-20th-century redbrick buildings and art galleries. It's the center of Seattle's arts scene and the galleries in this small neighborhood make up the majority of its sights.
Today's Yesler Way was the original "Skid Road," where, in the 1880s, timber was sent to the sawmill on a skid of small logs laid crossways and greased so that the cut trees would slide down to the mill. The area later grew into Seattle's first center of commerce. Many of the buildings you see today are replicas of the wood-frame structures destroyed by fire in 1889.
Nowadays, the role Pioneer Square plays in the city today is harder to define. Despite the concentration of galleries, the neighborhood is no longer a center for artists per se, as rents have risen considerably; only established gallery owners can rent loftlike spaces in heavily trafficked areas.
By day, you'll see a mix of Downtown workers and tourists strolling the area. Sadly, the local parks are mainly inhabited by homeless people. Pioneer Square has a well-known nightlife scene, but these days it's a much-derided one, thanks to the meat-market vibe of many of the clubs. If you want classier venues, you'll be smart to head north up First Avenue to Belltown or to select spots on Capitol Hill.
When Seattleites speak of Pioneer Square, they usually speak of the love they have for certain neighborhood spots—the original Grand Central Bakery in the historic Grand Central Arcade, Zeitgeist coffeehouse, a beloved art gallery, a friend's loft apartment, a great store—than the love they have for the neighborhood as a whole. Pioneer Square is always worth a visit, but reactions do vary. Anyone seriously interested in doing the gallery circuit will be impressed and foodies will find a few buzzworthy options. And the recently renovated Smith Tower, once the tallest building on the West Coast, beckons with an observation deck and a speakeasy on the 35th floor. That said, those looking for a vibrant, picture-perfect historic district that invites hours of contented strolling will be underwhelmed.
Pioneer Square is a gateway of sorts to the stadium district, which segues into SoDo (South of Downtown). First comes CenturyLink Field, where the Seahawks and the Sounders play. Directly south of that is Safeco Field, where the Mariners play. There's not much to see in this industrial area, but if you're a sports fan you can easily make a run from Pioneer Square to one of the stadiums' pro shops. There are also a few good brewpubs close to the stadiums.