Pioneer Square

To understand the early days of Seattle’s original downtown, charmingly characterized by brick facades and cobblestone streets, start at the Klondike Gold Rush National Historical Park (319 Second Ave S). This free museum chronicles the nearly overnight transformation the city underwent in 1897, when thousands of hopefuls passed through on their way to (fingers crossed) striking it rich in the Yukon. Seattle may not have been the final destination at the time, but there’s gold here these days—namely in the gilded elevator that whisks visitors to the top of Smith Tower (506 Second Ave), the tallest skyscraper west of the Mississippi when it debuted in 1914. Don’t miss sitting in the Wishing Chair or enjoying a refreshing beverage in the 35th-floor Observatory. For the opposite perspective, the Seattle Underground Tour (614 First Ave) offers a humor-filled walkthrough of the neighborhood’s subterranean passageways, once street-level sidewalks. If all these ups and downs have made you hungry, grab a custard-filled brioche donut at General Porpoise (401 First Ave S), a plate of oysters on the half shell at Taylor Shellfish Oyster Bar (410 Occidental Ave S), or a snow crab sushi roll at Matsu (501 Stadium Pl S). To quench your thirst, try the cappuccino al cacao or turmeric ginger chai at the flagship location of Italian-style Caffè Umbria (320 Occidental Ave S). Or if you’re in the mood for a glass of something red, white, or sparkling, stop by Browne Family Vineyards (413 First Ave S), Foundry Vineyards (524 First Ave S), or Locus Wines (307 Occidental Ave S), which all pour superb Washington wines in cozy tasting rooms. Cocktail connoisseurs will love Bad Bishop (704 First Ave) and Dead Line (114 First Ave S), both known for serving up vintage vibes along with well-crafted drinks. To really revel in Pioneer Square’s creative spirit, attend the First Thursday Art Walk, during which beautiful spaces like Glasshouse Studio (311 Occidental Ave S) and ArtXchange Gallery (512 First Ave S) stay open until 8 p.m. It’s the oldest art walk in the country, and yet another historic feather in the cap for this fabled neighborhood.