Never travel for business during Spring Break! That’s the first moral of this story as I always have to learn things the hard way… I booked a flight at the crack o’ dawn through Southwest so I could hit the ground running on a Monday morning to make the week last extra long. In theory, it’s a good idea during any other time of the year and you will fly through security at Phoenix Airport with time to spare. But this time was a Spring Break shit show at 5 a.m. with lines crawling down the hallway with the progression of a snail. Even telling them I had a flight to catch asap, they had that West Coast lackadaisical attitude that I have come to both love and hate of “relax, it’ll be fine”. After I finally got through and someone grabbed my luggage by mistake (why does that keep happening to me, I guess I must add a huge cat head sticker of my Carmella soon), I ran – and I’m not supposed to run with a scoliosis fusion “unless someone is chasing me” – with snow boots on and arrived 2 minutes too late to the gate a sweaty, wheezy and coughing mess from contracting the Arizona plague weeks prior. Fortunately, the amazing agent at Southwest took pity on me and got me on a flight through multiple California airports that would be a long haul but better than nothing at all. So I buckled up for it, glad I had packed some snacks but already exhausted.
But the time I finally arrived after my California airport tour, what a juxtaposition the Oregon airport was with its perfectly organized, pristine and clean aesthetic. It was even whisper quiet as I began the long, epic journey to pick up my rental car. Down the longest hallway that felt like a football field, I finally rolled out to Dollar Car Rental breathing like a linebacker. The woman went through her speel of get this insurance, do an upgrade, pre-buy this gas at a low price… then proceeded to gaslight me about a brand new Toyota Corrolla having 20 mpg and I’d have to fill up multiple times (I did just once and not even a full tank). I looked at her sideways and decided it was not worth it and just repeated, “No, thanks” for the fifth time. Ladies, if there’s anything I can tell you to get through this patriarchal life easier is know basic car knowledge… and shame on her for feeding into it. Any new car will usually get a minimum of 32 mpg on the highway – and this was a hybrid I was renting so even more. Well rested Cassie would have schooled her. But Cassie on no sleep and stressed AF was ready to GTFO.
It was during the drive out of Portland (which looks much like Philadelphia with its green signs and graffiti everywhere) that I decided to check into the hotel later that night and head straight to the first stop on the itinerary – a winery on a rolling hillside. And after my cell phone would not connect to the car’s newfangled port and Naggy (my dad’s word for the GPS lady) wasn’t vocally telling me where to go, I was ready to relax and in need of some wine down time immediately. The fluster of travel is real but the payoff is always worth it!
Welcome to the matriarchy of Lady Hill Winery! Located on the rolling countryside of the Willamette Valley, about 30 minutes west of Portland, Oregon, Lady Hill is a working farm and vineyard with a huge barn converted into a wine tasting room. This woman-focused 1,500 acre space has many generations of ladies steering the delicious ship into the land of tasty wines. Situated on the same land where co-owner Jerry Hill’s family has farmed since the 1850s, he brought his wife Elaine on board and have quite the crew of daughters since. And for the beer guys, don’t worry, they have beer on tap and wine pairing snacks available too. Who doesn’t love meat and cheese? Lodging is available with multiple campgrounds across the street or ask about the Auntie’s Airbnb!
It was at that point, I realized I had been happily floating around this zen space for almost 3 hours and needed to get settled into the hotel. Since I missed the lunch portion of things due to travel chaos, I was hoping they could offer dinner instead because I could feel the sleepiness coming on and did not want to drive anymore. Fortunately it all worked out and the Holiday Inn Portland I-5 South was super accommodating!
Don’t sleep on Holiday Inn! Or better yet, do sleep there as those super comfy beds lulled me to sleep for hours without waking for two nights in a row. And they have a great breakfast buffet each morning with fresh fruit and bacon as well as a pretty impressive restaurant attached Boonetown Bistro with strong cocktails, tasty steak and huge pizza pies. Individually owned and larger than the usual Holiday Inn, this space has almost 5 star ratings across the board and it shows! And Rack up those IHG travel points so you can use them all over the world.
Newly remodeled and the only full-service hotel in Wilsonville, Oregon, the location is key. Between downtown Portland (14 miles) and Woodburn Premium Outlets (15 miles), it is perfect to explore Lake Oswego, Tigard, Sherwood, Tualatin, Aurora, and Canby.
I was starving for dinner by this point and tossed my luggage inside and ran downstairs to stay in, relax, and enjoy a meal from BooneTown Bistro and Bar. On my walk down, I noticed this place was huge – with a convention space over 14,000 sq. ft. with seven break-out rooms perfect for conferences, company meetings, trade shows, parties and other social events.
What a wonderful walkabout at Graham Oaks Nature Park in Wilsonsonville, Oregon! With ample parking, restrooms and three miles of trails on the preserved 250 acres, it’s choose your own adventure time. As usual, I had no clue where I was walking to but just kind of followed my intuition, which led me to magical Hobbit-like paths of glistening in the rain wonder. Native wildlife abounds like white-breasted nuthatches, Western bluebirds, orange-crowned warblers and Western gray squirrels. Five plazas make great spots to learn about Graham Oaks’ history, from Kalapuyan tribes who gathered food to the family that farmed the land. Explore beyond the park on the regional Ice Age Tonquin Trail too! More park preservations like this need to happen around the world, it’s good for your lungs and your soul! After working up a walking appetite, it was time for lunch already.
Try saying McMenamins three times fast! It’s a tongue twister and McMenamins is a family-owned chain of brewpubs, breweries, music venues, historic hotels, and theater pubs in Oregon and Washington. Many of their locations are in rehabilitated historical properties; at least nine are on the National Register of Historic Places such as this one in Wilsonville, Oregon that all began in a church. Now the location has spread to another building with venue space in between and the best scavenger hunt around! With 56 locations total and 46 in Oregon alone including 12 historic hotels, 2 full-service spas, 6 soaking pools, 9 theater-pubs and more. 24 breweries, 2 distilleries, a winery, a creamery, coffee roaster, bakeries, produce and flower gardens, it’s safe to say this family has built an empire of sustainability.
Float through outer space at SoakBox! Always one to try anything once and twice if I like it, I agreed to float in salt water with Soak Box Spa, a concept born in Oregon with locations all over the place now. First you get a shower complete with body wash, shampoo and wear some ear plugs. Then climb into the tank with a wet washcloth for your face if needed and get lulled to darkness with relaxing music and twinkling sky-like lights. Once it was pitch-black (which is optional you can always open your pod door), I just closed my eyes and apparently fell asleep or into some sort of zen space. The next thing I know, the lights and music were back on and it was time to shower! They also offer an infrared sauna, cold plunge and more to rest, recover and recharge with a great deal for first timers.
It was sparkle beer for the win at Vanguard Brewing! This independent, veteran family-owned and operated craft brewery, tasting room, and beer garden in Wilsonville, Oregon was such a vibe, I stayed for way longer than planned which is always a great sign. In the back of the brewery, they were hosting Dungeons and Dragons night which I was kindly invited to but hadn’t played since college. The food was on point with local small business nods to flavors including the hazelnut flavor added to the beer! The ciders were perfectly on point and the weather was finally starting to warm up to enjoy the large outdoor beer garden. Keep slaying beer nerds!
I fell asleep without any doom scrolling or TV after the brewery, drifting off into my marshmallow bed at Holiday Inn Portland South until the alarm woke me up…
When you meet new friends, always have snacks! They gave me many goodies from Pearl Bakery so I was happy to share with my newfound Wilsonville, Oregon tourism friends when they picked me up out front of the hotel. It made them so happy and food really does unite everyone.
Right down the street in almost the same complex began our foodie trail in Wilsonville, Oregon! My trusty golf cart guide dropped me off for a decadent lunch and the most buttery lavender cupcake at Lux Sucre Desserts.
After this, I hightailed it out of town and to the next spot on my Oregon exploration with little time to spare. Press trips are usually tight on time but worth it in retrospect! I made a bunch of new friends, tasted new flavors and certainly want to return in the summer when the weather is just dreamy. My first visit to Oregon certainly won’t be my last and I’m glad it all started in Wilsonville, the perfect reprieve from the city of Portland.