The Ultimate 48-Hour Foodie Guide to Portland: Eat, Drink & Explore the Best of PDX

Welcome to the inaugural edition of my brand-new series, the 48 Hour Foodie Guide! In this exciting series, I’ll be meticulously mapping out how you can savor every delicious bite and sip your way through some of my most cherished destinations, all within a compact 48-hour window. And what better place to kick things off than a city renowned for its vibrant culinary scene and unique charm? Our first incredible stop is none other than the quirky, captivating, and downright delicious city of Portland, Oregon.

There’s something truly special about exploring a city with recommendations from someone who knows it intimately, almost as well as they know you. This past summer, I had the incredible opportunity to spend a memorable weekend in Portland, before embarking on one of the most epic road trips of my life. And let me tell you, it was an absolutely phenomenal experience. I’d always heard glowing reviews about the Pacific Northwest, but nothing could truly prepare me for the sheer magic that is Portland. The lush greenery, the towering ancient trees that seem to touch the sky, and hands-down the best bookstore I have ever set foot in (and I mean EVER) – it all combines to create an unforgettable atmosphere. If you find yourself with at least 48 hours to spare in this incredible Oregon gem, prepare to dive into a world of unforgettable flavors, unique sips, and sights that will steal your breath away. This comprehensive guide will show you how to experience the very best of Portland’s culinary and cultural landscape in a packed, yet perfectly paced, two-day adventure.

Where to Eat in Portland

McMenamins Kennedy School – McMenamins Kennedy School isn’t just a place to eat; it’s an entire destination within itself, and it’s my top recommendation for a holistic eat, drink, and explore experience. While Portland boasts several fantastic McMenamins locations, this particular spot truly stood out to me, primarily because of its fascinating past: it was once an elementary school! Yes, I admit, my inner history nerd was absolutely delighted. Transformed from a former schoolhouse, it now houses a fantastic array of amenities. You’ll find a full-fledged movie theater, multiple unique bars (including the cleverly named “Detention” bar, cleverly located in the old detention hall!), and several distinct restaurants, each offering its own culinary delights. This isn’t a quick stop; you need to dedicate an entire evening to fully immerse yourself in the charm and history of this place. Explore the hallways, find hidden nooks, and enjoy a meal and a drink in an atmosphere unlike any other. It’s a truly unique Portland experience, perfect for families, couples, or solo adventurers looking for something off the beaten path.

Everything you could want is here – a comfortable theater showing second-run films, several eclectic bars, and multiple dining options. There is even a bar named Detention in the old detention hall, which adds to the charm! You need to set aside an entire night and dedicate it to this place to fully appreciate its unique character and extensive offerings.

Blue Star Donuts + Coffee – Oh. My. Goodness. Blue Star Donuts + Coffee is an absolute revelation, and their donuts are nothing short of phenomenal. With several locations scattered across the city, these gourmet treats are a must-try for anyone with a sweet tooth. The moment I bit into their Mexican Chocolate donut, I was utterly captivated. The rich, spicy, and sweet flavors exploded in my mouth, making it incredibly difficult to share even a single bite (though, reluctantly, I did offer a taste to my partner, my ‘main squeeze’). Unlike traditional sugary donuts, Blue Star prides itself on using a brioche-style dough, which results in a lighter, less greasy, and more sophisticated pastry. Their unique flavors, like Blueberry Bourbon Basil or Passion Fruit Cocoa Nib, are crafted with high-quality ingredients and a focus on culinary excellence. Pair one of their exquisite donuts with a perfectly brewed coffee, and you have the ideal start to any Portland morning. They also completely understand the art of social media, so prepare for some Instagram-worthy shots!

Not to mention they just GET this whole social media thing – their donuts are as photogenic as they are delicious!

Kenny & Zuke’s Delicatessen – After an awe-inspiring visit to Powell’s City of Books (more on that under ‘What to See’ – prepare for tears of joy if you’re a fellow book lover!), we made our way to Kenny & Zuke’s Delicatessen for lunch. This place truly encapsulates the essence of a classic Jewish deli with a Portland twist, specializing in house-cured and smoked meats. Their Classic Reuben sandwich, crafted with succulent, melt-in-your-mouth beef pastrami, was beyond description. Each bite was a symphony of flavors and textures, literally melting in my mouth with every savory mouthful. The pastrami is cured and smoked in-house, giving it an unparalleled depth of flavor and tender quality. And because you can never have enough handcrafted pastrami, we also indulged in their beef pastrami cheese fries – a decadent, savory side that perfectly complemented the sandwich. Seriously, who doesn’t want to savor all that delicious, artisanal pastrami, all day, every day? It’s comfort food elevated to an art form, served in a bustling, friendly atmosphere that makes you feel right at home.

It literally melted in my mouth with every bite. Not to mention the beef pastrami cheese fries we got because who doesn’t want to eat all the handcrafted pastrami, all day every day? It’s an indulgence worth every single calorie.

Where to Drink in Portland

Multnomah Whiskey Library – The Multnomah Whiskey Library stands out as one of my absolute favorite discoveries on this trip, and honestly, it deserves a mention under both ‘Where to Eat’ and ‘Where to Drink’ due to its exceptional offerings. This isn’t just a bar; it’s an immersive experience, a must-embrace destination for anyone visiting Portland, especially if you have a deep appreciation for whiskey and scotch. While they offer a full range of beverages, their specialty truly lies in their unparalleled selection of spirits. What truly sets this place apart is its incredibly knowledgeable staff, often referred to as ‘librarians.’ Every team member is extensively trained on the vast collection of spirits, so you don’t need to be an expert. Simply describe your preferred flavor profile – perhaps something spicy, smoky, sweet, or robust – and they will expertly guide you to a perfect selection. I opted for a whiskey with a spicy kick, whereas my ‘main squeeze’ (I haven’t decided what I want to call him just yet on here… His actual name would just be too easy, right?) gravitated towards something wonderfully smoky. Both of us were utterly impressed with their precise recommendations and the quality of the drinks served. To top off this exquisite experience, their insanely delicious mac and cheese, enjoyed while lounging on plush leather couches in a dimly lit, cozy room that perfectly mimics an old-world library, truly made our entire night unforgettable. It’s a place where time slows down, and every detail contributes to a sense of luxurious relaxation and discovery. Be sure to check their reservation policy, as this popular spot can get quite busy.

They do have everything else there, but this is their undeniable specialty. All of their staff are trained on all of the spirits, so when you simply ask for a specific flavor profile, they will pick out something perfect for you. My partner and I were both so impressed with what we were served.

Plus their insanely delish mac and cheese, eaten on plush leather couches in a dimly lit room that looks exactly like an older library, made our whole night truly special. It’s an experience for all the senses.

The Goose – For an outstanding craft cocktail experience, look no further than The Goose. Their blood orange margarita was, without exaggeration, the best freaking margarita I’ve had in such a long time. The vibrant, intense flavor of the blood orange was so perfectly balanced and refreshing that it almost brought tears of pure happiness to my eyes. After a long day of walking everywhere, exploring the city’s many attractions, sitting down with a very potent and perfectly crafted margarita like that provided just the right ‘oomph’ of energy to reset and enjoy the rest of the evening. The interior boasts a wonderfully bright and cheerful ambiance, making it a fantastic spot to unwind and soak in the local vibe. Not to mention, their happy hour deals are absolutely legendary, making it an even more enticing option for an evening out. The Goose offers a diverse menu of other creative cocktails, local beers, and tasty bites, ensuring there’s something for everyone to enjoy in its lively setting.

Townshend’s Montavilla Teahouse – If you’re a devoted tea lover, Townshend’s Montavilla Teahouse is an essential stop for a refreshing break and a moment of tranquility. They offer an astonishing array of tea flavors, ensuring there’s something to delight every palate, from traditional black and green teas to exotic herbal infusions. Beyond the classic brews, they also feature some intriguing tea mixes and unique concoctions, including their famous kombucha. While I tend to be a purist when it comes to my tea, preferring it as simple and authentic as possible, I’m certainly intrigued enough to explore those unique combinations on my next visit. More than just a place for tea, it’s a super relaxed and inviting space where you can simply sit back, unwind, and recharge. It’s particularly ideal for a peaceful morning before you embark on your journey home or continue your adventures in Portland, offering a serene escape from the city’s hustle and bustle. The cozy atmosphere and friendly staff make it a perfect spot to relax and enjoy a quiet moment.

It’s also a super relaxed place to just sit back and relax, especially the morning before you head back to wherever your home may be. A perfect end to your Portland foodie journey.

What to See in Portland

Powell’s City of Books – If I were to choose a place to live permanently within a bookstore, Powell’s City of Books would undoubtedly be my sanctuary. This legendary independent bookstore is a true marvel, sprawling across an entire city block – it’s literally a city unto itself for bibliophiles. The sheer volume of books is staggering, with endless rows and towering shelves dedicated to every genre imaginable, from contemporary fiction and non-fiction to vast sections on travel, history, and art. I don’t think I’ve ever witnessed such an extensive collection of cookbooks in one place; I was practically drooling and swooning, contemplating spending every last cent I had right then and there. My absolute favorite highlight was their magnificent Rare Book Room, located on the top floor. The moment you step inside, you’re enveloped by the intoxicating scent of aged paper and leather – a true sensory delight for any book connoisseur. Their collection spans centuries, from ancient tomes dating back to the 1800s to hilariously illustrated cocktail books from the 1960s, complete with charming pin-up girl artwork. We easily spent a solid couple of hours browsing and getting lost in its literary treasures, but honestly, I could have happily spent days exploring every corner of this incredible establishment. Powell’s is more than just a store; it’s a cultural institution and a must-visit for anyone coming to Portland.

Moonstruck Chocolate Co – Craving a delightful treat to take home or simply enjoy on the spot? A visit to Moonstruck Chocolate Co. on charming 23rd Avenue is an absolute must. They craft some of the finest chocolates I have ever tasted, known for their artistic designs and high-quality ingredients. A particular standout was their innovative set of collaboration chocolates, featuring unique infusions from local Oregon breweries – they were incredibly good! Sadly, I only managed to savor one or two before a tragic incident involving a hot car backseat melted my precious stash during our road trip. Please, for the love of all that is holy, learn from my mistake: enjoy these exquisite chocolates immediately! Better yet, grab some and embark on a leisurely stroll up and down 23rd Avenue. This vibrant street, known as “Nob Hill,” is brimming with fun boutiques, charming cafes, and other unique shops, making it the perfect backdrop for snacking on your gourmet treats and soaking in the local atmosphere. It’s a delightful way to spend an afternoon in Portland.

Be sure to hit Will Leather Goods while you are there – they’ll even make you coffee while you shop! It’s the perfect blend of unique shopping and warm hospitality.

Bonus Side Trip: Bend, Oregon

If your Portland adventure allows for an extra day, I highly recommend embarking on a scenic day trip to Bend, a charming town nestled in the heart of Central Oregon. The drive from Portland to Bend is a breathtaking experience in itself, offering continuous views of lush, towering green trees that define the Pacific Northwest landscape. This journey through forests and along rivers is a photographer’s dream, providing ample opportunities to witness Oregon’s natural beauty firsthand.

Plus, when you get a clear shot of the majestic Mount Hood proudly peaking out over the verdant forests, you’ll undoubtedly find yourself pausing, taking a deep breath, and soaking in the awe-inspiring natural beauty. It’s a truly iconic Pacific Northwest vista.

Boneyard Beer – For dedicated beer lovers, a stop at Boneyard Beer in Bend is absolutely essential. This brewery has built a formidable reputation for producing some seriously robust and flavorful craft beers, which you can sample in their quaint and inviting tasting room. Among my personal favorites were their bold Diablo Rojo, a fantastic imperial red ale, and the classic Bone-A-Fide, a wonderfully balanced pale ale – both fantastic representations of their brewing prowess. Bend is a true craft beer mecca, home to numerous breweries, and Boneyard is a shining example of why its beer scene is so highly regarded. It’s a great spot to experience the local craft culture.

Deschutes Brewery Public House – Venture into the more central part of Bend and treat yourself to a delicious meal at the iconic Deschutes Brewery Public House. Their wide selection of beers on tap is consistently excellent, featuring their renowned flagship brews like Mirror Pond Pale Ale and Black Butte Porter, alongside seasonal and experimental offerings. Their thoughtfully crafted food menu pairs exceptionally well with their brews, creating a perfect culinary synergy with dishes ranging from hearty pub fare to more refined plates. After your meal, take a leisurely walk around the vibrant town center and along the picturesque Deschutes River. It’s the quintessential lazy beer day, offering a perfect blend of great food, refreshing drinks, and scenic beauty, making the drive to Bend entirely worthwhile for any foodie and beer enthusiast. The relaxed atmosphere and beautiful surroundings make it a perfect cap to your Central Oregon adventure.

You see? 48 hours to get the full Portland experience with a delightful side trip to Bend for a little extra Oregon thrown in is totally doable (and downright enjoyable)! From gourmet donuts and historic schoolhouse dining to world-class whiskey and iconic bookstores, Portland promises an adventure for all your senses. This guide ensures you make the most of every moment, savoring the unique flavors and unforgettable sights that make PDX truly special.

Now, the only pressing question that remains for me is… where shall I eat, drink, and explore next?