© Brian Jannsen / Alamy
Sarah Z. Wexler
September 30, 2015

Portlanders like to walk—whether it's on city streets or in the woods of Forest Park, whether it's sunny and 75 degrees, or gray and drizzly. Fortunately, walking is a great way to check out some of the city's history, plus a convenient excuse to pop into its best shops and restaurants along the way. Below, our favorite of the city’s walking tours, which offer the best of everything:

Underground Portland

In just one mile of trekking, the Portland Walking Tours underground tour (from $17) promises to cover “all the terrible, horrible, no good, very bad things from Portland's past,” and it delivers. You'll spend 75 percent of the tour above ground in the Old Town/Chinatown areas, learning about the history of the city's booze-smuggling, gambling, and “Shanghai-ing,” where drunks were supposedly smuggled out of the city through underground tunnels to be sold into work on ships. The coolest park of the tour, though, is when you're handed a flashlight and get to walk under the historic Merchant Hotel in an area that once led to the legendary “Shanghai Tunnels.”

Division Street’s Eateries

Division Street is best eating street in all of Portland, so start your walk hungry (note: this tour is free and self-guided). It’s stretch in the hip Southeast area is densely packed with food stops from 26th to 39th, including everything from casual, cheap eats (one of the city's best food truck pods) to finer dining (Ava Gene's, arguably one of the best meals in town). Some snack stops that are not to be missed: the Kati roll from Bollywood Theateris wrapped for an easy walk n' chew, Salt & Straw for a scoop of non-traditionally flavored ice cream, the Smaaken food truck for a waffle sandwich, or Roman Candle Baking Co. for a $5 slice of thick, square-cut pizza Bianca. Plus, you can stray to any of the cross streets to check out beautiful, 1900s-era Craftsman homes.

Mississippi Arts District

This restored historic area is now dotted with hip shops, galleries, and restaurants (note: this tour is free and self-guided). Pop into Land Gallery to see their current exhibit (previous ones include valentines inspired by the Talking Heads), then flip through cards and art prints in their shop. Check out Black Wagon, the coolest kids' store, for artsy books, slingshots, and tiny Vans. Stop for a craft cocktail at Interurban, a cool two-story bar with a great back patio, then finish with lunch or dinner of tacos and agua fresca at Por Que No Taqueria—there's always a line, but it moves quickly.

Sarah Z. Wexler is on the Oregon beat for Travel + Leisure. Based in Portland, you can follow her on Twitter at @SarahZWexler.

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