City Cast Portland logo

Get to Know Hillsdale

Posted on May 17, 2023   |   Updated on September 30, 2025
outdoor pool filled with people on a sunny day

Hillsdale has one of Portland Parks and Recreation's outdoor pools. (@portlandparks)

Hillsdale is like a visit to the suburbs without leaving the city.

It’s got your basic walkable Portland neighborhood amenities, even though you’re on the west side: a library, a farmers’ market on Sundays, plus a summertime pool on the campus of Ida B. Wells High School (formerly Wilson). But it feels like you’ve wandered into a hilly version of somewhere beyond city limits, with sprawling lots of tidy yards and spectacular views of Mount Hood, weather permitting.

map of hillsdale

Hillsdale is an inner southwest Portland neighborhood. (Google Maps)

Brewpubs:


The neighborhood has the claim-to-fame of the first brewpub to open in the state since Prohibition – after Oregon passed a 1985 law to legalize brewing and serving it on the same site, McMenamins Hillsdale Brewery & Public House opened with now-classic beers: Hammerhead, Ruby, and Terminator.

Sweets:


It’s worth a trip to the neighborhood just for Baker and Spice, which can lay a claim to some of the best-baked goods in the city. Try their croissants, something called a Katie bun, and the fruit-filled hand pies. Don’t forget the salted chocolate chip cookie, currently my favorite in town.

Hike:


If you’re looking for an urban hike, you can start in downtown Hillsdale and hike the streets up to the peak of Council Crest.

Share article

Hey Portland

Stay connected to City Cast Portland and get ready to join the local conversation.

Can't subscribe? Turn off your ad blocker and try again.

Neighborhood Guides

See All
Neighborhood GuidesOctober 4

Your Guide to Parkrose

Petting zoo, line dancing, and live music: Portland Fall Fest hits Rossi Farms on Oct. 4. Here’s how to make a day of it in Parkrose, plu...

A mural at 10721 NE Sandy Blvd. in Portland’s Parkrose neighborhood depicts farmers working in fields colored orange, red, and green. The blue-hued figures load yellow crates onto a blue truck.
Neighborhood GuidesSeptember 27

Your Guide to Kerns

When members of the Holy Trinity Greek Orthodox Cathedral moved into the large church at the corner of Northeast Glisan Street and 32nd A...

A street view from the corner of Northeast Glisan Street and Northeast 28th Avenue of the Apambichao Building, a cream and white colored Victorian apartment building that sits above Pambiche, a Cuban restaurant painted a deep blue.
Neighborhood GuidesFebruary 3

Your Guide to Oregon City

To Portland, Oregon City may be just a small suburb. (If you don’t even really know where it is, take 99 south past the Goodwill Bins and...

Pink, purple and yellow sunset views of the Willamette River at Willamette Falls
Neighborhood GuidesJanuary 21

Get To Know South Burlingame

Portland's South Burlingame neighborhood is small, but mighty. From lively cemeteries to neighborhood gems, here's everything you need to...

View of autumn trees at a cemetery.
Neighborhood GuidesDecember 8, 2025

Your Guide to an East Portland Neighborhood You’ve Probably Never Heard Of

Maybe you’ve never heard of the East Portland neighborhood Russell. But now you have: It’s an affordable, safe, and largely residential n...

trees line a paved path
Neighborhood GuidesNovember 10, 2025

The Neighborhood Hotspots in Family-Friendly West- and Eastmoreland

The charm of the Eastmoreland and Westmoreland neighborhoods is how great they are for the families that live there. Willamette Week’s ar...

people at tables at Monty's Red Sauce, Portland, Oregon
Neighborhood GuidesOctober 20, 2025

Your Guide to Hood River's Fruit Loop

Out near Hood River there’s a cluster of orchards and wineries along a 35-mile stretch of country roads. The area now goes by the attenti...

flowers in the foreground, Mount Hood in the background
Neighborhood GuidesSeptember 10, 2025

The Portland Neighborhood for Living in the Woods

Arnold Creek is a Portland neighborhood that you may never have heard of — maybe because it’s just barely inside city limits in Southwest...

map of Arnold Creek neighborhood. With Tryon Creek at the eastern edge.

The latest in Portland

Local CivicsOctober 29

Your Guide To the Fall 2026 Election in Portland

We’re closing in on Election Day 2026, so here's your guide to the key races and how to vote in the Portland area.

hand putting ballot into mailbox
The Weekly Wander by City Cast PortlandOctober 25

Side Quest: A Bubbly Backstory

Which backstory of downtown Portland’s Benson bubblers do you choose to believe?

A four-armed drinking fountain pedestal, known in Portland as Benson Bubblers, squirts water. Yellow leaves cover the bricks and some leaves have even landed in the bowls of the bubbler.
The Weekly Wander by City Cast PortlandOctober 22

Your Guide to Downtown Portland

Last caw! Don’t miss out on “Follow the Crows,” an interactive art trail in downtown Portland celebrating Laika’s upcoming film, “Wildwood.”

Downtown Portland’s skyline sparkles during blue hour. The perspective shows the view from Pittock Mansion, facing eastward.
The Weekly Wander by City Cast PortlandOctober 18

Side Quest: Drawing Nature into the City

Every award-winning park starts with a sketch. See the history behind one of Portland’s most famous green spaces.

Landscape design sketches from architect Lawrence Halprin show the vision for a tree-lined promenade in downtown Portland’s Open Space Sequence.
The Weekly Wander by City Cast PortlandOctober 18

Your Guide to Portland State University

There’s always something to do around the South Park Blocks, from the PSU Farmers Market to cultural celebrations like Catrinas en la Calle.

Two passengers walk onto the yellow and green Portland Streetcar beneath a leafy green canopy at the South Park Blocks stop on Portland State University’s campus.
The Weekly Wander by City Cast PortlandOctober 11

Side Quest: From Beyond the Grape

Frightful festivities from beyond the grapes await as Willamette Valley wineries host Halloween events. Throw on your costume and get rea...

Fog sits low among the fields and trees of Willamette Valley wine country. In the foreground, green grape plants show signs of fall as leaves begin to turn yellow.
The Weekly Wander by City Cast PortlandOctober 11

Your Guide to Tualatin

Don’t rock the gourd or you’ll miss Tualatin’s West Coast Giant Pumpkin Regatta when it returns Oct. 18. Join the fun and see what else t...

Two costumed people — one dressed as an aviator and the other in a squirrel suit — paddle their giant pumpkins toward the finish line at the West Coast Giant Pumpkin Regatta in Tualatin. Crowds of people cheer them on in the background.
Food & DrinkOctober 5

The Best Fall Foods in Portland

A fall festival at Bauman's Farm apples at a Hood River orchard (Kiyokawa Family Orchards, ideally), and a Sauvie Island pumpkin patch (B...

A pulled pork sandwich, soup, and apple cider slushy at Sugarpine Drive-In.