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The Ultimate Guide to the Best Things to Do in Hillside

The Ultimate Guide to the Best Things to Do in Hillside 

Most of the Hillside neighborhood in Portland consists of beautiful houses with striking views of the city and the mountains. However, a big part of it is also natural landscapes, restaurants, parks, and more. 

In fact, this quiet neighborhood can be a decent spot to go to when you’re looking for things to do in our city. If you want ideas for that, you’re on the right page – today, we’ll talk about the best things to do in Hillside! 

1. Explore Forest Park 

OPERATING HOURSMonday – Sunday 5 AM – 10 PM 

Forest Park takes up a good amount of the Hillside neighborhood. With it being 5,200 acres wide, it attracts a lot of wildlife, locals, and even tourists. 

There are a lot of activities that will keep you occupied in this park. These include cycling, walking, hiking, and running. 

If you’re into hiking, one of the most popular trails here is the Wildwood Trail. It’s a 30-mile long path and runs the length of the Forest Park itself!

It starts at W Burnside Road to the NW Newberry Road. One of the reasons it’s so popular is that it’s connected to a lot of popular destinations in the city. 

This includes the Stone House, the Pittock Mansion, the Washington Park, and Balch Creek Canyon. Those who want a full day of adventurous excursion would choose this trail to maximize their time. 

Another popular trail is the Macleay Park Trail. It’s much shorter compared to the Wildwood Trail (it’s only 5 miles!), so you can say it appeals to a lot of beginners. People even take their kids here! 

While it’s short, it’s perfectly okay if you don’t want to commit to the whole thing. You can turn around anytime you want – there’s really no pressure!

Oh, and if that weren’t enough, there are also available volunteering events from time to time in the park. They’re mostly about keeping the park clean and green, so to speak.

If you want to help with maintaining the beauty of the natural world that people can experience here, be sure to check out the Portland government’s website to look for the latest volunteer events there. 

Pro tip:
There’s a scenic viewpoint of St. Johns Bridge near the start of the Ridge Trail. Prepare your cameras or smartphones for it!

2. Tour the Pittock Mansion

ADDRESS3229 NW Pittock Dr, Portland, OR
CONTACT DETAILS+1 503-823-3623
OPERATING HOURSMonday, Wednesday – Sunday 10 AM – 4 PMTuesday 12 PM – 4 PM 
PRICEMembers: FreeAdults: $14.50Seniors (65+): $12.50Youth (ages 6–18): $10.50Children (under 6): Free

Pittock Mansion is a gorgeous French Renaissance-style mansion that sits on top of a hill. Because of that, it also offers gorgeous views of the city! 

If you’re lucky (which means you’re here on a clear day), you’ll see a nice view of Mount Adams, Mount Jefferson, Mount Rainier, Mount Hood, and Mount St. Helens. 

Plenty of people who go to the Pittock Mansion have done so after hiking through Forest Park, so feel free to add that to your itinerary as well. 

Anyway, to tell you more about the Pittock Mansion, it’s a 16,000 square ft home that was designed by Edward T. Foulkes.

There are 23 rooms inside, all of which are beautifully designed and preserved. The rooms include a Turkish sleeping room, a music room, a sewing room, and more. 

There’s rich history behind this home, so history buffs would also love visiting the Pittock Mansion. They offer guided tours too: just check their website to book. 

Aside from the mansion and the view of the city, you also shouldn’t miss passing by the Gate Lodge. It’s a craftsman home worth checking out if you like architecture – it’s right beside the original gated roadway that will take you inside the mansion. 

Pro tip:
We recommend visiting on weekdays to avoid crowds, especially during peak season (June to August and late November to December). We find it also best to reserve tickets beforehand. 

3. Try Phil’s Meat Market & Delicatessen

ADDRESS17 NW 23rd Pl, Portland, OR
CONTACT DETAILS+1 503-224-9541
OPERATING HOURSMonday – Saturday 9 AM – 6 PMSunday 10 AM – 3:30 PM 

Aside from experiencing the views and the popular destinations at the Hillside neighborhood, we also recommend dropping by this Hillside deli that we love. 

You can order things such as high-grade meat, bento, and sandwiches at Phil’s Meat Market & Delicatessen. It’s owned by a local butcher, so expect that they know how to spot the best meat. 

We’ve mostly tried their lunch menu (recommendations below!) but they also have different holiday menus, catering menu, and meat & seafood menu. 

We suggest getting a bite from their different food items to enjoy the different things they offer. 

Pro tip:
From their lunch menu, we recommend their Croque Philip. It’s a delicious sandwich made of ham, caramelized onions, gruyere cheese, arugula, and seared tri-tip. 
It’s topped with their delectable homemade cranberry barbeque sauce. Included in your order are chips, but you can get an upgrade to get the beer-battered sidewinder fries. 
They also have a create-your-own-burger option, so be sure to try that out as well. 

4. Purchase a jewelry item at Twist 

ADDRESS30 NW 23rd Pl, Portland, OR
CONTACT DETAILS+1 503-224-0334
OPERATING HOURSMonday – Saturday 11 AM – 6 PM Sunday 12 PM – 6 PM 

Twist is a store in the Hillside neighborhood where you can get quality jewelry. 

A lot of their designs are quite unique. From plain to really eye-catching ones, you’ll be able to find one to your liking. 

Twist carries pieces from no fewer than 120 designers, by the way, and the styles are definitely varied, as a result! There’s a designer who focuses on eras, beliefs, and cultures like Foundrae. 

There’s also a designer who focuses on making luxurious pieces for women like Anita Ko. Moreover, there’s one who hand finishes her pieces like Cathy Waterman, a designer who has been with Twist for 20 years. 

Pro tip:
Grab dinner afterward at the Ringside Steakhouse and let it be the cherry on top to your day. We find that their most popular food item is the prime rib and we totally agree with this! The portion is generous and the rib was cooked to perfection. We also recommend ordering the French onion soup. 
The steakhouse is a quick 5-minute walk from Twist. You can refer to the directions via Google Maps

5. Munch on some sushi at Fish & Rice

ADDRESS2332 NW Westover Rd, Portland, OR 
CONTACT DETAILS+1 503-954-1270
OPERATING HOURSSunday and Monday ClosedTuesday – Saturday 12 PM – 2:30 PM, 4 PM – 8 PM 

If you’re at Hillside and you have a sushi craving, we know the best spot you can satisfy that – Fish & Rice. 

While they serve sushi, they also have rolls, sashimi, nigiri, and poke bowls. Their name is quite literal, as you can see. 

They both have an indoor and outdoor seating, however the latter is quite weather-dependent. That’s why we recommend taking a table inside. 

Their indoor design is quite welcoming and comforting. It’s clean and minimalistic – quite similar to the Japanese aesthetic. 

We haven’t tried their entire menu yet (maybe soon!), but we have several recommendations below. 

Pro tips:
There’s limited parking in the area, so it may be better to take public transport in a lot of cases. 
Under their simple rolls menu, we recommend the spicy salmon because you simply can’t go wrong with that!
Under the special rolls, we suggest ordering their neskowin. It’s made up of torched salmon, avocado, dungeness crab, cucumber, and honey wasabi aioli. 

6. Relax at the Hand and Stone Massage and Facial Spa

ADDRESS25 NW 23rd Pl Suite 7, Portland, OR
CONTACT DETAILS+1 503-894-7163
OPERATING HOURSMonday – Sunday 9 AM – 9:30 PM

When you’re in the Hillside neighborhood, you also have the chance to relax by swinging by Hand and Stone Massage and Facial Spa. 

They have several services that are categorized into massages, facials, cryoskin, and hair removal. Since there are a lot to choose from, we’ll recommend what to try first from the different categories!

Under massages, we recommend the Swedish massage and the Himalayan salt massage. 

The Swedish massage is best for beginners while the Himalayan salt massage is probably best if you like hot stone massages and need something to exfoliate your skin.

Meanwhile, under the facial, we recommend the Classic Facial because it focuses on a lot of skin problems such as congestion, sensitivity, fine lines, loss of firmness, and lack of radiance. 

As for the Cryoskin category, we recommend the Cryoskin Facial Toning. With the use of hot and cold temperatures, this procedure would help lessen the fat cells and make the skin firmer. 

Pro tip:
If you live in or near Hillside, check out the membership programs available at their website to get the best deals. They offer better discounts for those than with their one-off special promos. 

7. Purchase drinks at Uptown Wine + Beer + More

Purchase drinks at Uptown Wine + Beer + More
Image from Uptown Wine + Beer + More
ADDRESS1 NW 23rd Pl, Portland, OR
CONTACT DETAILS+1 503-227-0065
OPERATING HOURSSunday and Monday ClosedTuesday – Saturday 11 AM – 6 PM

You can grab all the drinks you want and need at the Uptown Wine + Beer + More. They serve a variety of whiskey, scotch, vodka, tequila, gin, and rum from different brands. 

Purchase drinks at Uptown Wine + Beer + More 2
Image from Uptown Wine + Beer + More

The wines are pretty varied too – most of their options are from California, Pacific Northwest, and Europe. 

Meanwhile, they also have products from local breweries that are worth checking out. If you’re interested in getting to know more about the local brews, you’ll get a chance of getting more acquainted with that here. 

Pro tip:
Aside from liquor, they also have cigars available, so be sure to check those out as well! 

8. Take photos at the Kings Height Staircase

Take photos at the Kings Height Staircase
Image from Places For Everyone 
ADDRESS1209 NW Summit Ave, Portland, OR

Kings Height Staircase is a photospot that we think everyone should go to at least once if they’re in the Hillside neighborhood. 

It’s not much of a climb (73 steps) and the view on top is spectacular! We don’t see why you can’t give this staircase a try. 

Not a lot of people have heard about this spot so if you want a free, unhindered view of the Portland skyline, you know where to go next. 

Pro tip:
There are a lot of hidden staircases just like this all over Portland, each acting like a portal to a different destination. In fact, there are plenty of people who document the different staircases, making it like an Easter egg hunt all over the city. 
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