Oregon's Charming, Historic Neighborhood Brims With Walkability And 'Old Portland Gems'

Portland's Hollywood neighborhood is a unique part of the Oregon metropolis, with the green suburban landscape feeling like a small city within the city. Sprinkled throughout are what Travel Portland calls "old Portland gems," which can transport you to various points in the city's history. You can take a MAX ride to the Hollywood-NE 42nd Ave. stop and spend some time on foot here, stopping in at the bars and cafes along the way. Thanks to the MAX's Red Line, the neighborhood is only a 20-minute train ride from the Portland Airport.

The neighborhood is small, covering less than one-fifth of a square mile, surrounded by Northeast Thompson St., NE 36th Ave, NE 47th Ave, and Interstate 84. While it may not be classically charming like Laurelhurst, the dreamy neighborhood across the freeway, the grittier Hollywood has the charm of Old Portland. Old bars and new restaurants alike line the streets, helping the neighborhood embrace multiple eras of Portland simultaneously.

The neighborhood is centered on its namesake, the historic Hollywood Theatre, on Northeast Sandy Boulevard. The programming is an eclectic mix of new movies, cinema classics, and arthouse films. You can even take classes on film and television appreciation taught by local film professors. An ornate facade adorns the front of the building, giving it an old-world European theater look. The theater first opened in 1926. Before that, the neighborhood was named Hollyrood, which was changed shortly after the theater opened.

Another vestige of the old Portland appeal, albeit one nowhere near 100 years old, is Antique Alley, located in the basement of the 42nd Street Station. Opened in 1985, Antique Alley is a collection of around 100 vendors selling their second-hand goods. Here, you can find some pieces of Portland's rich thrift shop history. Portland is still a thrifting capital, which makes it one of the best cities to travel to for a budget shopping trip.

Another bit of Portland history started in the 1990s when pinball became popular. The magazine Multiball began growing a culture around the game, and while the magazine is long gone, the culture still exists to this day. The city has a competitive league for the game with matches all over the city. One venue that hosts matches is Hollywood's Wedgehead. The bar has 21 well-kept machines out at any time, from its collection of over 150.

Everything in Hollywood is reachable on foot, as the neighborhood has an impressive Walk Score of 94 out of 100. You can even take a Positively PNW Walking Tour to learn about the architecture of the district. You'll see the neighborhood's many old homes of varying styles, built along beautiful tree-lined streets. 

Hollywood has several new restaurants — all in walking distance of each other — that are able to shine in one of the top five foodie cities in the U.S. Gado Gado is an Asian fusion restaurant with multiple James Beard nominations. Sit outside on the charming, maximalist patio with iridescent tables and gauzy curtains. The space provides a pocket of beauty in the neighborhood. From Gado Gado, it's a three-minute walk to the Portland staple Sam's Billiards (open since 1962) to play some pool. It's low-key and has two floors of pool tables, so you won't have to wait long.

If chilling with tropical cocktails and high fidelity music playing from giant speakers is your idea of a perfect night out, take a two-minute walk from Sam's Billiards to The Sonder Bar. The listening bar has a unique, relaxed Portland appeal, and it allows people to bring in crates of their own records to listen to on the bar's impressive sound equipment.