Categories > Guides and Tips
Your Local’s Guide to Exploring Healy Heights Like a Pro
- Where is Healy Heights?
- What is the main street in Healy Heights?
- How to Get to Healy Heights
- What to Do and See in Healy Heights
- Go for a walk or hike in the neighborhood
- Spend the whole day at Oaks Amusement Park
- Enjoy nature at Westmoreland Park
- Where to Eat and Drink in Healy Heights
- The Observatory
- Leaky Roof Gastro Pub
- The Eastburn
- Where to Shop in Healy Heights
- East Borough Shop
- Pioneer Place
- Tender Loving Empire
- Where to Stay in Healy Heights
- Hotel Lucia
- The Society Hotel - Portland
- Portland International Guesthouse
- FAQs
Perched above Portland’s Southwest Hills, Healy Heights is where nature meets luxury.
It’s one of the city’s best-kept secrets, where you can often find yourself above the clouds on foggy mornings.
Whether you’re chasing skyline sunsets or just curious about what million-dollar homes in Portland look like, Healy Heights is the place to go.
Where is Healy Heights?
Healy Heights is a distinct neighborhood in Portland’s Southwest Hills, located west of Hillsdale in the city’s southwest area. It’s within the boundaries of the Southwest Hills neighborhood, but is considered a neighborhood on its own.
What is the main street in Healy Heights?
Healy Heights offers access to several major routes. Located just off SW Council Crest Drive, the neighborhood sits above downtown, with access to SW Patton Road and SW Fairmount Boulevard.
How to Get to Healy Heights
Via bus: Take the bus at SW 5th & Pine. Make sure to take the Line 8 bus. This is a direct line to reach SW Terwilliger & Sam Jackson with no stops. Once there, you’re already in Healy Heights.
Via private car: If you’re coming from downtown Portland, start by taking SW I‑405 S. Then, merge onto US‑26 W (Sunset Highway) toward Beaverton. Take the exit for SW Barbur Boulevard and follow the signs.
Continue along before turning right onto SW Capitol Highway. About a mile, turn left onto SW Council Crest Drive. Take another quick left onto SW Patrick Place. Healy Heights is just ahead.
If you’re coming from Portland International Airport, head west onto I‑84 W going downtown. Merge onto I‑5 S. Take the exit for Pioneer Square and continue onto US-26 W (Sunset Highway).
From there, exit at SW Barbur Boulevard and follow the previously mentioned steps.
What to Do and See in Healy Heights
1. Go for a walk or hike in the neighborhood
Healy Heights is one of the most scenic places in Rip City, so a quick run up the neighborhood is a must. You can start the day in Hillsdale and climb 1,000 feet to read the summit near Council Crest.
One of the best stops along the way is Keller Woodland, which opens into nearly 40 acres of Douglas fir forest. The trails are quiet, and the trees will make you forget you’re in the city – just make sure you take the trails while the sun’s still out.
Past the woodland, you’ll come by Hessler Hills, which is a secluded neighborhood with luxury views. You’ll see the same thing along Fairmount Boulevard, where you’ll find joggers, dog walkers, and cyclists along the road.
2. Spend the whole day at Oaks Amusement Park
Media credit oaksamusementpark
Address: 7805 SE Oaks Park Way
Phone: +15032335777
Operating hours:
- Tuesday – Wednesday: 10:00 AM – 7:00 PM,
- Thursday & Sunday: 12:00 – 7:00 PM,
- Friday – Saturday: 12:00 – 8:00 PM
Open since 1905, Oaks Amusement Park has that old-school charm that both kids and parents love. There’s a good variety of rides here: the classic Tilt-A-Whirl, a roller coaster, and a little train that circles the park.
One of the highlights here is the roller skating rink. It has everything: benches for watching, a snack bar, and a beginner’s area for practice. If you want to give it a shot, skates are available for rent, or you can bring your own.
Before you go, make sure to grab your parking pass, which you need to display in your car. And keep in mind that GPS can mess up and send you to the wrong lot – drive all the way to the end of the road until you see the entrance!
3. Enjoy nature at Westmoreland Park
Media credit woody_adams
Address: 7530 SE 22nd Ave
Phone: +1 503-823-2525
Operating hours: Monday – Sunday: 5:00 AM – 12:00 AM
Love nature? Westmoreland Park is the perfect spot for that afternoon escape alone. Here, you’ll find towering cedars that provide shade for the wide open space. There’s plenty of room for Frisbee or a nice picnic.
If you’re bringing kids along, they’ll definitely love that nature play area. There’s a massive sand pit with working water pumps, plus giant logs and rocks to play around with. It’s all built with natural materials!
Between the duck pond, casting pond, and quiet spots along the creek, it’s easy to spend hours here. You may even spot a few herons while you’re there, so grab a camera to snap the moment.
Where to Eat and Drink in Healy Heights
1. The Observatory
Media credit: theobservatorypdx and pdx.biz
Address: 8115 SE Stark St
Pricing: $
Operating hours: Tuesday – Saturday: 11:00 AM – 10:30 PM, Sunday – Monday: 11:00 AM – 10:00 PM
Good to know: Offers many American classics
Website
The Observatory is the perfect spot for those craving American staple food. The prices are reasonable, ranging from $20 to $30 per person. It also has a nice atmosphere that’s ideal for hanging out with friends.
For brunch, the biscuits and gravy are enough for a light start. But for dinner, you may want to go heavy with a lamb burger with roasted peppers and goat cheese. Serving is big and yes, it’s as juicy as you can imagine.
The place is popular, so it tends to fill up fast. Reservations are the way to go, but if you can score a seat walking in, it’s just as good too – the waiting time isn’t too long. There’s a small parking lot at the back, and we recommend coming early to secure a space.
2. Leaky Roof Gastro Pub
Media credit: theleakyroof
Address: 1538 SW Jefferson St
Phone: +15032223745
Pricing: $
Operating hours:
- Tuesday: 3:00 PM – 9:00 PM,
- Wednesday – Saturday: 10:00 AM – 9:00 PM,
- Sunday: 9:00 AM – 2:00 PM
Good to know: Live music
Website
The Leaky Roof isn’t something to skip in Healy Heights, especially if you just want to have a great time and even better food. Even the Reuben with fries is a treat – crispy, savory, and definitely filling.
There are many comfort foods too, though the chicken and waffles are often among the stars. The waffles are light and perfectly golden, which matches perfectly with the crispy and juicy fried chicken.
For something much heavier, the smash burger is the best choice. The portions are generous – something you can split for two to enjoy – and all the seasonings are well-balanced. With Moscow Mule, this meal is a real treat.
3. The Eastburn
Media credit: theeastburn
Address: 1800 E Burnside St
Phone: +15032362876
Pricing: $
Operating hours: Monday – Saturday: 8:00 AM – 11:00 PM, Sunday: 8:00 AM – 10:00 PM
Good to know: Best for cocktails and draft beer
Website
If you want good food without breaking the bank, The Eastburn is a great start. The elk sausage is a premium choice here, often paired by regulars with warm and cakey biscuits. There’s even a vegetarian version of this with mushroom gravy.
For breakfast, the eggs Benedict is always a strong choice – it’s perfectly poached with rich hollandaise that complements the flavors. With chocolate chip French toast on the side, it’s a filling choice to get the day started.
If you want something heavier, you can get the mac and cheese with smoked brisket paired with a dark porter. The brisket is smoky and tender, with a slight crunchiness thanks to the frico on top.
Where to Shop in Healy Heights
1. East Borough Shop
Media credit: eastboroughshop
Address: 6354 SW Capitol Hwy
Phone: +15037525018
Pricing: $
Operating hours: Tuesday – Sunday: 12:00 PM – 6:00 PM
Good to know: Best for gift hunting
Website
East Borough is a great stop if you want to do some gift hunting. You can find almost everything here, from European stationery to Katha blankets. Prices are okay but vary largely depending on the product – you can spend anywhere from $10 to $100.
There are also many cute, handpicked items featured on the shelves, including acorn candles and embroidered bandanas. It’s no wonder that many locals consider this their go-to for housewarming gifts and self-care splurges.
If you get lucky to meet the owner, Amy, you may find yourself having a nice afternoon chat as you browse the shelves. If you’re lucky, you may even get to take home some free gifts, though they only usually do this when there’s a celebration.
2. Pioneer Place
Media credit: pioneerplace
Address: 700 SW 5th Ave
Phone: +15032285800
Pricing: $
Operating hours: Monday – Saturday: 11:00 AM – 7:00 PM, Sunday: 11:00 AM – 6:00 PM
Good to know: Wide range of stores
Website
If you’re looking for a one-stop shop for everything, just drop by Pioneer Place. This mall has many luxury and casual stores, including outlets for Gucci, H&M, and Zara. For tech, there’s also an Apple Store inside.
The food course is on the lower level, and even though the food options are average, they’re enough for anyone grabbing a quick bite. If you come by lunch, though, stores usually have long lines, so bring some patience!
It’s easy to get to the area, as there is a MAX line nearby. If you’re bringing a car with you, you can pay for parking at 4th SmarkPark. It won’t cost you over $4 for 2 hours, so it’s great in case you need plenty of shopping time.
3. Tender Loving Empire
Media credit: tenderlovingempire
Address: 412 SW 10th Ave
Phone: +15035482925
Pricing: $
Operating hours: Monday – Sunday: 11:00 AM – 7:00 PM
Good to know: DIY kits, custom printing, and artisanal bath goods
Website
To score some unique finds, Tender Loving Empire is a solid option. Here, you’ll find a good mix of Portland-made gifts. There are colorful prints, enamel pins, handmade jewelry, and self-care goodies.
If you want to grab a few items for friends back home, you can check out their Portland-themed merch too. You can grab some T-shirts, magnets, and stickers in bulk at reasonable prices.
Love music? Then you shouldn’t miss their music nook. The store doubles as a record label, and you can actually preview local artists before buying their vinyl or even cassettes. It’s just a fun way to discover new artists!
Where to Stay in Healy Heights
1. Hotel Lucia
Media credit: hotel_lucia
Address: 400 SW Broadway
Phone: +15032251717
Pricing: $$$
Operating hours: Monday – Sunday: 4:00 PM – 12:00 PM
Website
Hotel Lucia is a fab choice for those who want an artsy downtown escape. The lobby alone has cozy vintage furniture and a rotating collection of Portland-inspired photography – they set the mood right away!
The rooms are compact yet thoughtfully designed. If you want to go all out, though, you can book the 250-square-foot Superior King. It has large windows and curated art on the walls.
There are even bigger rooms that are about 750 square feet, complete with all high-end amenities. It’s definitely expensive, but it may be a better value if you’re splitting the costs with friends or your family.
As for amenities, there’s a mini arcade downstairs. You’ll find a pinball machine and a retro Street Fighter game that’s totally free to play. Then, there’s happy hour at 5:00 PM that comes with complimentary drinks.
2. The Society Hotel – Portland
Media credit: societyhotel
Address: 203 NW 3rd Ave
Phone: +15034450444
Pricing: $$
Operating hours: Monday – Sunday: 3:00 PM – 11:00 PM
Website
If you’re looking for a budget-friendly hotel that’s full of character, The Society Hotel is a solid pick. It’s just a minute’s walk to the Lan Su Garden and the Japanese American Museum of Oregon.
There are different room options – from hostel-style bunk beds to private rooms and full suites. Their premium suites are still quite affordable for what they offer – with a weekday deal, you can book this option for as low as $69 per night
If you’re travelling solo, especially by train or plane, this hotel makes sense. It’s only a five-minute walk to Union Station and is closely connected to the MAX line. This makes getting around the area much more convenient.
3. Portland International Guesthouse
Media credit: nwportlandhostel and hosteling.us
Address: 2185 NW Flanders St
Phone: +15032240500
Pricing: $$
Operating hours: Monday – Sunday: 2:00 PM – 11:00 PM
Website
Portland International Guesthouse is a great choice if you want a clean, quiet, and affordable place that feels more like a home than a hotel. Everything here is spotless and well-maintained, from their bedrooms to the shared bathrooms.
For a private and spacious room, you can book the Flanders Suite downstairs, which comes with its own kitchen and bathroom. It’s great for small families and groups of friends that need to stay for at least a week or longer.
One of the best things here is how walkable everything is. You’re just a block away from Trader Joe’s, and it’s an easy stroll to Washington Park and the Rose Garden. You won’t likely need a car for your entire stay.
