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How to Have the Best Time at Hillsdale, Portland

How to Have the Best Time at Hillsdale, Portland

If you find yourself in Portland, one of the neighborhoods you shouldn’t miss is Hillsdale. It’s a lovely place in the city that’s full of life and entertainment. 

In this article, we’ll take a closer look at how you can make the most of your time in Hillsdale. This is your chance to have an unforgettable experience in this unique Portland neighborhood.

1. Enroll in circus classes at Trampoline Town


Address: 8130 SW 11th Ave, Portland, OR

Contact details: +1 503-290-9372

If you don’t have any idea what circus classes are, they’re classes that teach you different skills involving aerial arts (like aerial hoops), acrobatics, and more. 

This doesn’t necessarily train you for the day you’ll join the circus per se, but rather it helps improve your physical fitness and strength in a fun way! 

Anyway, Trampoline Town offers numerous classes for adults and kids. They even have private classes which are available for 1 to 6 students. 

Moreover, you can also book them for special events like birthdays so you can share the fun with family and friends. 

Pro tip:

Trampoline Town’s classes are usually fully booked, so make sure to join the waitlist to know when you can enroll. Fill up the form here

2. Play games at Burlingame Park


Address: SW 12th Ave &, SW Falcon St, Portland, OR

Operating hours:

  • Monday to Sunday – 5 AM to 12 AM

Even though a huge chunk of Portland exudes urban charisma, there are still places like Burlingame Park that show just how much natural resources thrive in the city. 

This park is set in a quiet neighborhood, making it ideal for relaxing. Plus, this spot also welcomes people to play in the 50 ft. play area. You can even reserve it for soccer or softball games!

Pro tip:
If you’re in the area, might as well drop by the nearest diner – Vertical Diner. Unlike other usual diners, this one’s specifically for vegans. Know how to get there via Google Maps.

3. Take your dog on a walk at Hillsdale City Park


Address: SW 27th Ave & Hillsdale Hwy, Portland, OR 

Contact details: +1 503-823-7529

Operating hours:

  • Monday to Sunday – 5 AM to 12 AM

Hillsdale City park is quite a popular park in the area. It’s big and it’s dog-friendly. 

It’s 5 acres wide and there’s a 2-acre space specifically for when you want to take your dog off the leash. 

Come to this area and you’ll be able to see a lot of dog parents playing with their dogs! We know dog lovers wouldn’t miss swinging by here. 

Pro tip:
After a day at Hillsdale City Park, we suggest going to Sasquatch Brewery if you’re famished. Despite its name, it’s not only a drinking spot, but they also serve quality dishes. That said, we think having the chance to try the local brews here is a plus! Know how to get there with the help of Google Maps.

4. See a historical landmark at Henry E. Dosch House

4. See a historical landmark at Henry E. Dosch House
Image from Wikipedia


Address: 4825 SW Dosch Park Ln, Portland, OR 

Henry E. Dosch House is a historical landmark in the Hillsdale neighborhood. 

To give you a bit of a background, Henry E. Dosch was a German immigrant, local merchant, and someone who was a part of Oregon Horticultural Society and Lewis and Clark Centennial Exposition. 

The house was built in 1890, but it’s well-preserved. The house itself isn’t the only thing fascinating about it though: the trees around it are just as old as the house. 

Pro tip:
After a trip to this old house, we suggest grabbing some coffee and pastries at Baker & Spice. It offers a cozy ambiance and it smells nice inside too! See how to head there via Google Maps.

5. Get some delicious brunch at Gigi’s Cafe


Address: 6320 SW Capitol Hwy, Portland, OR

Contact details: +1 503-977-2233

Operating hours: 

  • Monday to Sunday – 8 AM to 3 PM 

Gigi’s cafe offers a lot of great breakfast and brunch options. However, their waffles are what they most recommend. 

They have the basic options which are liege waffle, brussels waffle, and cornbread jalapeño waffle. Moreover, they also have sweet and savory options! 

Pro tips:

  • Waffle breakfast sandwich was something everyone at Rip City Review thoroughly enjoyed that we had to order another plate for us! 
  • Their other dishes are also good! Try at least one of their hashes.

6. Discover a hidden gem at Spunky Monkey Coffee Kitchen


Address: 7900 SW Barbur Blvd, Portland, OR

Contact details:  +1 503-234-1600

Operating hours:

  • Monday, Saturday, & Sunday – closed
  • Tuesday to Friday – 7:30 AM to 1 PM 

Spunky Monkey Coffee Kitchen’s full of character, much like its name. You’ll also never have trouble finding this place because its purple exterior stands out in a neighborhood full of gray houses. 

They offer coffee, bagels, tea, and sandwiches – all of which are quite delicious. Whenever we’re in the Hillsdale neighborhood, expect us to drop by this place to get us some bagels! 

Pro tip:

There are so many delicious things on the menu that it’s impossible to recommend a few of their dishes. That’s why we’re going to say to try as much as you can to get the full Spunky Monkey experience!

7. Try authentic Mexican cuisine at Casa Colima Mexican Restaurant & Cantina


Address:  6319 SW Capitol Hwy, Portland, OR

Contact details: +1 503-892-9944

Operating hours:

  • Monday to Thursday, Sunday – 11 AM to 9 PM
  • Friday & Saturday 11 AM to 9:30 PM 

Casa Colima is a famous Mexican restaurant in Hillsdale. To give you an idea of the food they serve, they have salads, soups, meat, enchiladas, vegetarian, chicken, burritos, and many more of your favorite Mexican dishes. 

From their dishes up to their interiors, it seems that Casa Colima is dedicated to providing an authentic Mexican experience. 

Pro tip:

A few dishes that definitely stood out from the rest were tacos tacoman (authentic street style tacos), fajitas de pollo (chicken fajitas), and deluxe burrito. 

8. Taste Mexican classics at Verde Cocina Hillsdale


Address: 6446 SW Capitol Hwy, Portland, OR

Contact details: +1 503-384-2327

Operating hours:

  • Monday to Friday – 11 AM to 9 PM 
  • Saturday & Sunday – 10 AM to 9 PM

Another Mexican restaurant option for all you foodies out there is the Verde Cocina. This one fuses Northwest influence with Mexican classics with local ingredients, giving you unique dishes that will make you want to keep coming back. 

One of their most raved about dishes is the carne asada, which is steak served with veggies, mashed potatoes, and chimi-roja salsa. 

Pro tip:

They also serve wine, margaritas, cocktails, and beers, making this a great spot to drink in if you’re looking for something more laid-back. 

9. Experience luxury at Chart House


Address: 5700 SW Terwilliger Blvd, Portland, OR 

Contact details: +1 503-246-6963

Operating hours:

  • Monday & Tuesday – 4 PM to 9 PM 
  • Wednesday to Saturday – 11:30 AM to 9 PM 
  • Sunday – 11 AM to 9 PM

If what you’re looking for is something more luxurious and sophisticated, you should try Chart House. Chart House is a seafood restaurant that serves their meals super fresh. 

While most of the items on their menu are sea-based, they also have a few beef, chicken, and pork options. 

There’s a fantastic view outside the window that shows the Willamette River and the surrounding mountains, making it not just about the food, but the overall experience itself. 

And for those who are counting their calories, there’s no need to try to compute it in your head when you dine in here because it’s already written on the menu. 

Pro tip:
Their signature dishes include slow-roasted prime rib, which you have to try on your first visit.

10. Enjoy vegan dishes at Vertical Diner and The Gold Room


Address:  8124 SW Barbur Blvd, Portland, OR

Contact details: +1 503-206-6150

Operating hours:

  • Monday to Sunday – 10 AM to 8 PM 

Vertical Diner and The Gold Room is pretty rare – it’s not everyday that you’ll see a diner that’s especially for vegans!

They have all-day breakfast (and even build your own breakfast), burgers, burritos, sandwiches, and many more. Yes, all of that’s vegan!

Everything they serve is 100% plant-based, so you can indulge yourself in their dishes while still being confident that you’re eating healthy meals. 

Pro tip:

If you’re on an all gluten-free diet, you’ll also love this place because they indicate on their menu what’s safe for you to consume. 

11. Experience local beers at McMenamins Hillsdale Brewery & Public House


Address: 1505 SW Sunset Blvd, Portland, OR 97239, United States

Contact details: +150-324-63938

Operating hours:

  • Monday to Thursday, Sunday – 11 AM to 10 PM
  • Friday & Saturday – 11 AM to 11 PM 

The city of Portland is filled with numerous local breweries, so of course, this list wouldn’t be complete without at least one or two brewery recommendations. 

They have a lot of drinks on tap like blackberry cider, lunchtime lager, and woolly mammoth. 

Aside from alcoholic drinks, they also have several delicious food options like fish & chips, burgers, sandwiches, snacks, and a lot more! 

Pro tips:

  • Surprisingly, this McMenamins is also kid friendly! They have a menu just for kids.
  • Ask their servers when and what time their happy hour is so you can know when you can get drinks for $1 to $5 off! 
  • Their burgers are so good – the beef patty is so tender and juicy! You have to try at least one of their many burgers. If you were to ask us what our favorite is though, it’s the Dungeon (served with Swiss cheese and grilled mushrooms). 
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