Map: Pioneer Square

Seattle’s first downtown, Pioneer Square hosted a diverse group of pioneers, immigrant fishermen, and gold prospectors during the city’s mid-19th-century founding years. Today, fifty ornate Richardsonian-Romanesque brick buildings, built immediately after the 1889 Great Seattle Fire, mix with Native American totem poles, art galleries, bookstores, and coffee shops.

Start at (1) Pioneer Square Park (www.pioneersquare.org), First Avenue and Yesler Way, a small triangular-shaped green space marked by two National Historic Landmarks: a restored 1909 cast-iron pergola, built to shelter cable car passengers, and a 60-foot-tall (18-meter-tall) cedar totem pole. Stolen from an Alaskan Tlingit tribe in 1889 and gifted to Seattle, the current totem pole is a reproduction of the original, which was burned by an arsonist in 1938.

Across the park, enter (2) Doc Maynard’s Public House (610 First Avenue), an 1890s saloon turned live music venue, to purchase tickets for the popular Underground Tour (www.undergroundtour.com). Led by joke-telling guides, the 90-minute tour takes you below the area’s sidewalks, into the now-closed underground that once served as a red light district.

Walk east on Yesler Way to (3) Smith Tower (506 Second Avenue; www.smithtower.com), Seattle’s first skyscraper, built in 1914. “When tourists are in town, I like taking them here instead of the Space Needle,” says Anna Roth, Northwest editor, citysearch.com. “It’s steeped in local history.” Take the manually operated elevator to the 35th floor and visit the Chinese Room, with an elaborately carved ceiling and furniture, and an observation deck, with expansive city views.

Back on the ground, return to First Avenue and walk southeast to (4) Elliott Bay Book Company (101 South Main Street; www.elliottbaybook.com). “It’s not the biggest bookstore in the Northwest, but simply the best,” says Chris Clayton, arts and culture editor, Seattle Magazine. In its brick and pine interior, browse through hundreds of tomes—don’t miss the bargain used-books room.

Walk south on First and turn left on South Jackson Street. Visit (5) Jean Williams Antiques (115 South Jackson Street; www.jeanwilliamsantiques.com) for armoires, chandeliers, mirrors, and other goods from the 18th and 19th centuries. Next door, (5) Stonington Gallery (119 South Jackson Street; www.stoningtongallery.com) displays works in glass and wood by master artists from the Pacific Northwest Coast and Alaskan tribes.

At the intersection of South Jackson and Second Avenue, enter the (7) Klondike Gold Rush National Historical Park (www.nps.gov/klse/). Participate in the interactive exhibits to learn about the 1890s Gold Rush that brought a boom to Seattle, which served as a major staging point for prospectors heading to Alaska.

Turn left on Third Avenue South and walk one block west to pick up a deli sandwich at (8) Salumi (309 Third Avenue South; www.salumicuredmeats.com). Get it to go, and turn left on South Main Street. Grab a bench at (9) Occidental Park, a cobblestone gathering place with totem poles and a display on the history of the neighborhood, and enjoy your meal. Cross the park to enter your last stop, the historic (10) Grand Central Arcade (214 First Avenue South) full of antique and collectible shops. Reward yourself with a freshly baked dessert at (11) Grand Central Bakery (214 First Avenue South; www.grandcentralbakery.com.)

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