Sensational Mother-Daughter Trip To Portland, OREGON

A whirlwind mother-daughter trip to Portland OR spanning 48 hours meant we had to make the right decisions about what to see and do. But Portland which has so many nicknames—Portlandia, PDX, and City of Books—clearly offers lots of possibilities.

I visited Oregon’s most populous city in March 2019. My 20-something daughter (Claire) and I wanted to do everything. I recommend that you research your options carefully so you can correctly choose between wineries, farm-to-table restaurants, food trucks, gardens, Mt. Hood, or yes even legit marijuana dispensaries. 

mother-daughter trip to Portland OR

Mother-Daughter Trip to Portland

Claire and I chose two wineries in Willamette which were located less than one hour from Portland. Even though Portland typically will require raincoats and umbrellas in March, we had a bright sunny day. I started my morning at Starbucks by 6:30 a.m. because Portland is three hours behind my body clock. I was welcomed by two such friendly baristas who were soon recommending wineries to visit. When I accidentally spilled my café latte, it was replaced with a smile—no charge. Northwesterners are so darn friendly! I also sampled donut balls and beignets from Nola Donuts.

Tour Pearl District

Next, I spent an hour exploring the Pearl District, which is Portland’s warehouse-turned-hip home to restaurants and shops. Imagine walking past scores of art galleries and gazing in the window. I just wish I had been in town for their First Thursdays in the Pearl evening art gallery tour. Plus Claire and I would definitely jump right into the Pearl District Bunny Hop. There’s also Art in the Pearl Festival, Craft Beer and Cider Festivals, Holidays in the Pearl, and the Holiday Tree Lighting at Jamison Square.

Book Brunch

By 9 a.m., Claire and I were headed to Sunday brunch. We chose Tamale Boys because it featured different regions of Mexico for the breakfast options—huarache de tamal, huevos rancheros, sopa de huevos, chilaquiles, tamales, and pastel Azteca (imagine Mexican lasagna).

Through his restaurant’s menu, owner Jaime Soltero Jr. is educating the Northwest on how diverse Mexican food and culture are.

Tamale Boy’s picnic tables allowed us to soak up the sun while we scarfed our guacamole. The restaurant features an exotic mural which of course Claire and I used as the backdrop for the first-of-many selfies. Before we left the restaurant, I wandered up the street to see The Wishing Tree. This bountiful tree is tagged with hundreds of paper tags in a rainbow of colors—blue, yellow, orange, red, and green—with handwritten wishes. My favorite was a two-year old who “wants to see a doggie.” 

Tour J. Christopher Vineyard

Next up was our afternoon visiting two wineries located in Newburg, Oregon. If you love wine, I suggest you plan a week-long visit because Oregon is home to distinct coastal wine regions—coastal and inland. Since we were based in Portland, we focused on North Willamette Valley (north of Portland). It is famous for its Pinot Noir (representing 73% of all wine grapes grown in the WV). And it is less than an hour’s drive from the city.

Our first stop was J. Christopher Vineyard. Its mountain perch allows wide lens views of the mountains. Although we didn’t get to meet the vineyard’s German shepherd dogs, we did get to hear stories about them in the tasting room. There is the adorable photo of the owner’s puppy framed in the tasting room. We were the first visitors to arrive on this Sunday morning, so we enjoyed a leisurely tasting of six wines. Candace agreed to explain the nuances of the winery’s most popular wine.

Discover Compris Vineyard

Next to visit was a vineyard founded by a former NASA scientist who worked on the Apollo mission in the 1970s. His circuitous path to running a winery involved executive stints in Silicon Valley before he and his wife settled down to run a winery. Don and his wife Vicki Hagge purchased the land in 1999 and proceeded to open Vidon, a boutique vineyard. They sold it during the pandemic. In May 2023, the new owners – Dru and Erin Allen – will celebrate the first anniversary of Compris Vineyard. It offers stunning views of rolling wine country hills and Mt. Jefferson.

Portland winery scene

Share A Picnic

Although we had planned to visit a third Newberg winery, we chose instead to buy a bottle of wine and sit outside on the recliners. Our companions were two roosters on the lawn and a cat watching us from the balcony of the owners’ house. They were ideal companions for our mother-daughter trip to Portland OR.

The winery is situated in the Chehalem Mountains. The terrace view was hypnotic—hazy blue sky, puffy clouds, rugged fir trees, and the softly-curving mountain range. I felt like I stepped onto the canvas of a Monet painting. Vidon is also ideal for an al fresco lunch on the terrace if we had opted to bring a picnic hamper.

Sample Cideries

We couldn’t leave Oregon without sampling its cideries; the heirloom fruit is harvested from orchards stretching from the Columbia River Gorge to the Willamette Valley to Southern Oregon. We chose a Portland cidery for our tasting. The open-air restaurant offers dozens of ciders featuring Oregon-grown fruit. You can even buy a six-pack to take home (if you are willing to check your luggage.) Hard cider has joined the rank of beverages made (and indulged) in Portlandia!

Visit Powell’s City of Books

No visit to Portland is complete without the mandatory crawl through Powell’s bookstore (established 1971). Note that I did not say run, race, or fast walk. This block-long bastion for book lovers demands that you stay for a LONG time because you are now a resident of the “City of Books.” I completely lost track of the time because every single book seemed to call out, “Terri, check me out!”

Our evening ended with snacks on the rooftop of our Couch 9 rental apartment which is conveniently located next to Avid Cider Co. Portland’s skyline is multi-jeweled. To the right lies the bright red spires of the bascule Broadway Bridge (built in 1913). Tall modern edifices loom both far and near as the Pearl District transforms from a grey warehouse enclave to a modern home for art galleries, restaurants, Powell’s City of Books , high rise condos, and warehouse-to-loft conversions. And in the distance, Mt. Hood stands guard over this City of Warmth—exactly what we found on our mother-daughter trip to Portland OR.

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  • Chrissy J
    March 30, 2019 at 3:40 pm

    I am from here, and I am SO happy to see you enjoying our awesome city.

    I am one of the new people here. But I look forward to every single post!!