You’ll find no shortage of unique sights, attractions and eateries in Portland, Oregon, from boutiques and gardens to a 19th-century French Renaissance-style château in the hills.


During my recent four-day stay in the Rose City, I explored its compact downtown, got out on a foodie bike tour and checked out a few vibrant neighbourhoods.


Pittock Mansion
Henry Pittock was born in London, England but grew up in Pittsburgh, Pennsylvania. In 1853, when Henry was 19, he headed west on the Oregon Trail to seek his fortune. A year later, his future wife Georgiana Burton left Missouri with her family and headed West as well. When Henry and Georgiana arrived in the area, Portland was a frontier “stumptown”, competing with Oregon City to become a major trade and industrial center for the region.


Henry found work as a typesetter at The Oregonian at a time when the newspaper industry faced both financial risk and heavy competition (over 30 newspapers were launched in Portland during this period). On June 20, 1860, Henry and Georgiana married and five months later, Henry was given ownership of the paper in exchange for back wages. He went on to transform The Oregonian into a successful daily newspaper still in print today.

[Turkish smoking room painted domed ceiling created by artist Harry Wentz]

Mr. Pittock was also an avid outdoorsman, bicycle enthusiast, and amongst the first to climb Mount Hood. Georgiana Pittock became a founder and fundraiser for several charities and cultural organizations, including the Ladies Relief Society, Women’s Union, and the Martha Washington Home, a residence for single, self-supporting women.

Henry and Georgiana moved into the home in 1914 with eight other members of the family. The last residents, grandson Peter Gantenbein and his father, Edward, moved out in 1958 and put the mansion up for sale.


In 1965, the Pittock Mansion opened to the public as a historic house museum. The Mansion contains gorgeous interiors and while most of the pieces are not from the original owners, they were donated by families who lived in the area at the time, to give a close approximation of how the home might have been decorated in its heyday.


Portland is an ideal city for touring on a bike, and with that, I booked a three-hour foodie cycling tour with Cycle Portland (180 NW 3rd Avenue).


Once we’re outfitted with bikes and gear, our guide explains the itinerary and soon we’re cycling along the Portland waterfront and make our way over to our first stop in NE Portland, Ranger Chocolate Company. We warm up with a hot cup of coffee and a single origin dark chocolate sample from Peru.


Our next stop, Cartopia, is Oregon’s original food cart pod. A heart-warming satay sauce poutine is just the ticket as we enjoy the heated tent during this particularly wet afternoon.


The East Bank Esplanade offers nice views of Portland, including the iconic Portland white stag sign, leading us to the world’s longest floating bike path before making our way back to the shop. Tours can be reserved for up to 12 riders, and Cycle Portland can also customize tours.


South Park Blocks
In the 1850s, early Portland settler Daniel Lownsdale had a visionary plan for a greenway that would extend from the northwest waterfront to the southwest hills.

While his dream was never fully realized, some of the blocks set aside by Lownsdale eventually became what is now known as the South Park Blocks.

The first elm and poplar trees were planted in the park blocks in the 1870’s. Between 1908 and 1912, additional landscaping included rose gardens, while fountains and statues were installed in the 1920’s. For a lovely morning stroll, take in the South Park Blocks en route to other destinations in downtown Portland, including the Portland Art Museum.

[Jeffrey Gibson, They Come From Fire, currently on exhibit at Portland Art Museum]

Portland Art Museum
Portland Art Museum, the seventh oldest in the US (and the oldest on the West Coast), is internationally renowned for its permanent collection and ambitious special exhibitions drawn from the Museum’s holdings and the world’s finest public and private collections.

Their massive collection of over 42,000 objects, displayed in 112,000 square feet of galleries, reflects the history of art from antiquity to present. The Museum is dedicated to preserving great art for the enrichment of future generations, and devotes 90% of its galleries to its permanent collection.


Cruise the Willamette River
Enjoy Portland views from the water on a two-hour Portland Spirit Cruise, boarding at Salmon Springs Dock (1010 SW Naito Parkway).

Spanning 300 km (187 mi) long, the Willamette River is Oregon’s largest and flows from south to north, a rare occurrence in the Northern hemisphere. And did you know that the Willamette is home to 31 native- and 29 non-native fish species within its waters?


The area is still largely inhabited by Kalapuyans (of the Kalapuya tribe) in addition to Chinook, Clackamas and Molalla peoples.

The cruise travels from Portland to the Historic Milwaukie Waterfront, taking in several bridges and notable sights. It’s a relaxing way to spend a couple of hours, rain or shine, while learning a few historical tidbits of the region.


Portland Spirit also offers lunch, brunch and dinner cruises and can cater holiday, private and wedding events.


Dolly Olive (527 SW 12th Avenue) allows simple, high quality ingredients to speak for themselves. Chefs Kasey Mills, Natalie Gullish and Patrick Lynch create lovely seasonal creations in addition to an in-hour pasta program (and daily focaccia offering).

[Dolly Olive’s Bucatini with Spicy Prawns]

The menu strikes a balance between Italian specialty products and local ingredients from suppliers such as Cowbell Creamery and Prairie Creek Farm.


The Daily Feast (837 SW 11th) offers all-day brunch in a cozy, diner-style space. Their menu includes faves such as avocado and egg on toast, muesli pancakes and homemade biscuits and gravy. This friendly establishment is also popular with the lunchtime crowd and features an expanded beverage menu plus classic shakes and floats for a sweet treat.

[NW 23rd neighbourhood aka Nob Hill]

If you’ve decided to explore the cute shops and cafés (several located inside Victorian era homes) along NW 23rd Ave, the colourful Santa Fe Taqueria (at 831) makes for a great refuelling stop.

[Santa Fe Taqueria]

They’ve got a great selection of burritos, tacos, pupusas, chicken tortilla soup plus an entire section of their menu devoted to vegan diets. Be sure to ask for plenty of their tasty homemade salsa to smother over your meal!


Located inside the Moxy Hotel (585 SW 10th Avenue), the fun vibe inside the hotel’s own Food Cart Alley includes Let’s Roll, offering a selection of poke bowls, salads, sushi burritos and other tasty delights.

Iron Chef winner and Top Chef competitor Justin Sutherland is the Alley’s chief collaborator and works with the hotel team to give local purveyors the opportunity to showcase their culinary talents within the modern downtown hotel.

Check out the Food Cart Alley when you’re in town, as both seasoned and up-and-coming chefs are part of the scene here.

[Freshly-made pasta at Grassa]

With a few locations around town (as well as Vancouver, Wash. and Lake Oswego), Grassa (Lardo’s sister restaurant) offers a small but lovely selection of homemade pasta dishes, paired with traditional and seasonal salads, tasty cocktails as well as a few wines on tap.

[L to R: Grilled Butternut Squash, Spring Pea Ravioli]

I highly recommend the spring pea ravioli topped with ricotta, asparagus, yuzu butter, mint and crispy prosciutto. It’s spring in a bowl!

Their grilled butternut squash topped with pecorino and crispy sage is also a winner.


Mother’s Bistro moved to a new location at 121 SW 3rd in 2019, and the main room boasts light yellow walls adorned with vintage lighting fixtures and photos.

Comfort food and traditional homemade favourites bring both locals and visitors back time and again to enjoy Mother’s homemade biscuits, egg scrambles, wild salmon hash as well as a full lunch and dinner menu, including Pastry Chef Debbie Putnam’s sweet creations.


Cheryl and Ed Casey started out with a catering business, and continue to cater events while testing new dishes at Sheryl’s on 12th (customers request particular dishes for their weddings, bar mitzvahs and parties). In turn, they innovate and “beta test” new recipes; once an item becomes a hit, it goes onto the regular menu.


There is no shortage of cool shops and boutiques to explore throughout Portland! Book lovers will want to make their way to Powell’s City of Books, the largest used and new bookstore in the world. Throughout its 10 colour-coded rooms, you’ll find every topic under the sun, as well as a selection of gifts, t-shirts and knick-knacks.


For a beautifully curated collection of local products, Made Here PDX (40 NW 10th Avenue) is filled with food, home, apothecary and apparel items and is an easy walk from Powell’s. They currently carry over 200 brands and products can be ordered via their website and shipped internationally.


Originally launched as a record label, Tender Loving Empire is also locally-focused (Oregon + PNW).


[Tender Loving Empire]

The husband and wife team (Brianne and Jared Mees) have built an “empire” with several locations (including an outpost at Portland International Airport) with future plans to open at Seattle International Airport. A small room in the back features local record releases in order to support Oregon musicians.


Nearby Woonwinkel contains Dutch-designed products, and having lived in The Netherlands for eight years, I just had to make my way to their shop at 935 SW Washington. While Woonwinkel is small in size, the unique collection is well worth checking out. Plans are underway to expand their current retail space, and I look forward to seeing more of Dutch designers represented in Portland.

Top images: Ground Kontrol Classic Arcade, 115 NW 5th Avenue; Pine State Biscuits, 1717 NW 23rd Avenue

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