I firmly sit on opposing ends of the spectrum as both a perpetual traveler and a homebody. There is no middle ground for me. I find myself frequently visiting the same airports within a 24-hour period, as O’Hare has witnessed my presence quite often recently. Similar to how books and food inspire me, travel motivates me to seek more from life, enhancing my capacity for empathy and challenging my previously held beliefs with new ideas. Therefore, when I was given the task of writing a guide for what to do in Portland, Oregon, I eagerly seized the opportunity to write about my favorite city.
At the age of 22, I made the daring decision to move across the country to Portland. As a New England native, my new friends, co-workers, and acquaintances were dumbfounded to learn that I impulsively relocated to Portland with just my bike and a suitcase, still uncertain of my employment situation. However, my move was far from impulsive. I had first visited the city at the age of 15, during a trip to Seattle with my mother to visit family friends. And although I regret to inform you that I have never experienced love at first sight with a romantic partner (I’m rather slow in matters of the heart), my infatuation with Portland began even before our train reached Union Station.
Upon arrival in Portland, it’s not the cityscape that captivates you initially. Instead, it’s the awe-inspiring sight of Mt. Hood’s gently curved peak that indicates you’ve arrived in a special place. Within just a few hours of your visit, you can feel the pervasive atmosphere of creativity and innovation. And, of course, the food is outstanding as well. The image featured above showcases the beauty of the Portland Japanese Garden, captured by Roman Johnston.
Although I have since moved away from Portland (life’s twists and turns have taken me to Chicago and beyond), the allure of this city remains with me. It’s where I met my closest friends, my partner (whom I can now confirm I’m deeply in love with – Portland may have played a part in that), and where my identity and self-understanding truly blossomed. Who knows, if you spend a weekend in Portland, it might have the same transformative effect on you.
When I initially left Portland, I gifted one of my best friends with my favorite Portland print. To solidify the exchange, she requested that I write a few words reflecting my eternal love for the city. While the words below specifically pertain to Portland (Grocery Outlet – if you know, you know), I hope they resonate with you, wherever you happen to reside. Portland evokes a sense of nostalgia for the anticipation of rain, the quirky finds only available at St. John’s Grocery Outlet, and the people who embrace and accept you when you’re at your most vulnerable and unfiltered. Portland deepens your understanding of community and what it means to contribute and offer yourself to a world that will wholeheartedly embrace you with love beyond your wildest imagination. At times, living a life as beautiful as the one you experience in Portland may feel indulgent, or even impossible. Yet, you somehow perpetually feel nostalgic, knowing that the present moment is precious and will always remain with you, no matter where you go, wherever you are, or wherever you will ever be. And now, let’s explore the Camille Styles Portland City Guide.
What to Know About Portland:
When is the Best Time for a Weekend Trip to Portland?:
Having lived in Portland for four and a half years, I can confidently say that I’ve experienced it all. From the rare snowstorms that bring the city to a standstill (and leave my Smart Car unusable), to scorching heatwaves reaching 116 degrees that made me realize I have reverse seasonal affective disorder, to the two weeks in 2020 when we couldn’t step outside due to wildfire smoke. Unfortunately, while climate change affects everywhere, the Pacific Northwest seems to bear the brunt of it. With that being said, my two favorite times of year in Portland are the middle of fall and early spring. Early spring boasts stunning cherry blossoms, and although I can never get enough of the rain, many Portlanders will tell you that this is when they celebrate the return of the sun. However, nothing compares to the fall in Oregon. Due to the lingering summer heat that extends into September, fall starts a bit later than in most other northern parts of the US. Late September through early November showcases beautiful foliage and comfortable temperatures that bring a touch of autumnal chill.
How to Get Around:
Depending on where you’re staying, public transit can be a drawback in Portland. The MAX light rail is reliable for downtown travel and connects Portland to neighboring suburbs, but it may not take you to the hidden gems located in Portland’s various quadrants. However, it is a convenient option if you’re staying at one of the centrally-located hotels or want to avoid the expense of an Uber to the airport. In addition to public transit, there are other transportation options available. Portland is renowned for being an incredibly bike-friendly city, making cycling one of the best ways to explore. During the warmer months, you can utilize the city’s bike share system called BIKETOWN (owned by NIKE, pronounced the same), which offers affordable transportation to any destination you desire. If you prefer driving, I recently discovered Turo, a car rental company, on my last visit to Portland. Turo is available in many cities across the US and internationally, offering a more cost-effective alternative to traditional car rentals. It’s similar to Airbnb but for cars. I simply retrieved my cute white Fiat from its nearby parking location at the owner’s residence and returned it at the agreed-upon time. It was a hassle-free experience.
Where to Stay: Best Portland Hotels:
1. Hotel Grand Stark: This is one of the newer hotels in the city and has quickly become a beloved gem in Southeast Portland. I first encountered Palisociety, the hotel group to which it belongs, when I stayed at Palihotel in Seattle. If you’re seeking a cozy yet stylish place to sleep and spend time, Hotel Grand Stark is an excellent choice. It is situated in inner SE Portland, within walking distance of several bars, restaurants, and coffee shops along SE Stark Street. Additionally, a short drive can take you to Belmont Street or East Burnside, where you can find some of the city’s finest dining and drinking spots. If you prefer not to venture out, the hotel’s restaurant, Bar Chamberlain, provides a classic and brasserie-like dining experience.
2. Ace Hotel: What can I say about Ace Hotels that hasn’t already been written? They have establishments all over the world and have maintained their unique and charming aesthetic. Each hotel draws inspiration from its building’s previous uses, whether it be a former halfway house (Seattle), a historic YMCA (Pittsburgh), or another former hotel (Portland). Staying at the Ace will undoubtedly provide insight into the city’s history. If you’re seeking a downtown experience, the Ace Hotel is unbeatable. It’s just a minute’s walk from my favorite local cinema, Living Room – if you have the time, I highly recommend checking it out. Furthermore, the hotel is surrounded by some of the finest eateries on Portland’s west side. Don’t wait, book your room now.
3. The Hoxton: As the photos demonstrate, The Hoxton exudes unparalleled style and sophistication. With mid-century lighting, modern low couches, and an abundance of plants, you may be tempted to spend your entire trip within its walls. Tope, the rooftop bar and restaurant, provides some of the best city views, along with delicious tacos and tequila-based cocktails in my opinion. Alternatively, you can visit Lovely Rita for exceptional Pacific Northwest fare. Little Rita Coffee Bar is also a great option for your daytime coffee fix. By staying at The Hoxton, you can have a complete culinary experience without leaving the confines of the hotel.
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