Your Ultimate 48-Hour Foodie Guide to Portland: Eat, Drink, Explore

Welcome to the inaugural edition of my “48 Hour Foodie Guide” series! In each installment, I’ll be sharing my insider tips and favorite spots to truly experience a destination through its culinary and beverage scene – all within a vibrant 48-hour timeframe. Our first unforgettable stop on this gastronomic adventure? The captivating city of Portland, Oregon.

There’s something uniquely special about exploring a city with the insights of someone who knows it intimately, almost as well as they know you. My recent summer weekend trip to Portland, strategically timed before an epic road trip, was nothing short of incredible. While I’d always heard glowing reviews about the Pacific Northwest, no amount of anticipation could truly prepare me for the sheer wonder that is Portland. The city captivated me with its lush greenery, towering ancient trees, and undoubtedly the most impressive bookstore I’ve ever encountered (and I’m a serious bookworm!). If you find yourself with at least 48 hours to spare in this vibrant Oregon gem, get ready to embark on a journey filled with exceptional food, unique drinks, and must-see attractions. This guide is crafted to ensure you savor every moment and experience the true essence of Portland.

Where to Eat in Portland: A Foodie’s Delight

McMenamins Kennedy School

My top recommendation for a comprehensive Portland experience that combines dining, drinking, and entertainment is undoubtedly McMenamins Kennedy School. While Portland boasts several McMenamins locations, this particular one stands out with its incredibly unique history and atmosphere – it’s a former elementary school, charmingly repurposed into a vibrant community hub. This quirky transformation truly appeals to my inner history buff!

This establishment offers an incredible array of amenities under one roof: a movie theater, multiple bars, several restaurants, and even a heated soaking pool. Imagine sipping a craft beer in a bar aptly named “Detention,” located in the school’s old detention hall – the charm is simply irresistible. You could easily spend an entire evening here, hopping from one unique space to another, enjoying delicious food and drinks, and soaking in the distinctive ambiance. It’s an ideal spot to kick off your 48-hour Portland adventure, offering something for everyone.

Blue Star Donuts + Coffee

Prepare yourself for a truly sublime donut experience at Blue Star Donuts + Coffee. These aren’t just any donuts; they are an absolute revelation. With several locations scattered across the city, Blue Star has perfected the art of donut making, particularly with their signature brioche dough that achieves a perfect balance of lightness and richness. My personal favorite, the Mexican chocolate donut, was so intensely flavored and utterly decadent that it almost brought me to my knees. I had to summon every ounce of willpower to share even a bite or two with my partner, though it was a reluctant sacrifice!

Beyond their incredible flavors, Blue Star also understands the modern foodie experience, creating beautifully presented treats that are as photogenic as they are delicious. Each donut feels like a work of art, making them a popular choice for social media enthusiasts. A visit here is essential for any sweet tooth looking to indulge in Portland’s renowned donut culture.

Kenny & Zuke’s Delicatessen

After immersing ourselves in the literary paradise of Powell’s City of Books (more on that below), we made a strategic stop at Kenny & Zuke’s Delicatessen for a much-anticipated lunch. This classic Jewish-style deli is celebrated for its commitment to handcrafted meats, and their Classic Reuben sandwich, featuring tender beef pastrami, was nothing short of divine. Each bite was a symphony of flavors and textures, literally melting in my mouth.

And because one can never have too much expertly prepared pastrami, we also indulged in their beef pastrami cheese fries – a decision I highly recommend! This spot is a must-visit for anyone craving hearty, flavorful deli fare that speaks to the soul. It’s the perfect spot to refuel and enjoy some truly comforting food amidst your Portland explorations.

Where to Drink in Portland: Craft Beverages & Cozy Vibes

Multnomah Whiskey Library

The Multnomah Whiskey Library is an establishment so exceptional, it truly deserves a mention in both the “Where to Drink” and “Where to Eat” categories. This unique venue was, without a doubt, one of my absolute favorite discoveries of the entire trip. It offers an immersive experience that you simply must embrace fully during your visit. While they cater to all tastes, this library is a true haven for connoisseurs of whiskey and scotch.

What makes this place truly stand out is its impeccably trained staff, who possess an encyclopedic knowledge of all their spirits. Simply describe your preferred flavor profile – perhaps something spicy, smoky, or sweet – and they will expertly guide you to the perfect selection. I opted for a whiskey with a spicy kick, while my partner (my “main squeeze,” as I affectionately call him for now) leaned towards a smoky dram. Both recommendations were absolutely spot-on, a testament to their skill and passion.

Adding to the exquisite drinks, their outrageously delicious mac and cheese, enjoyed from plush leather couches in a dimly lit room that perfectly emulates an old-world library, completed our evening. The ambiance alone is worth the visit, creating a sophisticated yet incredibly cozy atmosphere that transports you to a bygone era. It’s an essential stop for a memorable evening in Portland.

The Goose

For cocktail enthusiasts, The Goose offers what I can confidently say was the best margarita I’ve had in a very long time. Their blood orange margarita, in particular, boasted such an intense and refreshing flavor that it almost brought tears of joy to my eyes. After a day spent exploring Portland on foot, a potent and perfectly balanced margarita like this provided the much-needed “oomph” to reset and energize for the rest of the evening. The interior of The Goose exudes a bright, welcoming, and genuinely happy vibe, making it a fantastic place to unwind.

Don’t miss their happy hour, which offers incredible deals on their delicious concoctions. It’s a vibrant spot, perfect for mingling with locals and soaking in Portland’s friendly atmosphere.

Townshend’s Montavilla Teahouse

If you’re a tea lover, or simply seeking a tranquil break from coffee, Townshend’s Montavilla Teahouse is your sanctuary. This delightful teahouse offers an impressive array of tea flavors, catering to every palate. While they also feature intriguing tea mixes (I personally prefer my tea in its purest, simplest form), I’m keen to experiment with those creative combinations on a future visit. It’s clear they have a passion for all things tea, ensuring a unique experience.

Beyond the extensive menu, the teahouse itself provides a super relaxed environment, ideal for unwinding after a day of sightseeing. It’s an especially perfect spot to enjoy a calming cup the morning before heading back home, offering a peaceful start to your journey.

What to See in Portland: Beyond the Bites

Powell’s City of Books

If I could choose to live inside any bookstore, Powell’s City of Books would be my permanent address. This isn’t just a bookstore; it’s an entire universe of words, spanning an entire city block with endless rows and rows of literary treasures. I was utterly mesmerized, especially by the sheer volume of cookbooks – a true paradise for any foodie! My jaw was practically on the floor, and I had to actively resist the urge to spend every last cent I possessed. The most enchanting part of my visit was discovering their rare book room on the top floor. The moment you step inside, the distinct, comforting scent of aged paper and history envelops you.

This special room houses everything from ancient texts 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, but honestly, I could have happily lost myself there for days. It’s a profound experience for any book lover and a definitive must-see attraction in Portland, offering a quiet escape into the world of stories and knowledge.

Moonstruck Chocolate Co

Looking for a delightful treat to savor or bring home as a souvenir? Make your way to Moonstruck Chocolate Co on 23rd Ave. They craft some of the finest chocolates I’ve ever tasted. I was particularly impressed by their unique collaboration chocolates with local Oregon breweries – these were incredibly delicious and truly innovative. Tragically, I only managed to enjoy one or two before they met an untimely demise; I discovered them tragically melted in the back seat of the car during our road trip, before I had a chance to fully appreciate them. Please, for the love of all things holy, learn from my mistake! Head to the store, buy your chocolates, and enjoy them on the spot.

While you’re on 23rd Avenue, take the opportunity to stroll up and down the street. It’s brimming with charming boutiques, unique shops, and other enticing spots to explore, making for a perfect afternoon of shopping and snacking.

Will Leather Goods

As you explore 23rd Ave, be sure to pop into Will Leather Goods. This exquisite shop offers a stunning collection of high-quality leather products, from bags to accessories. What makes the experience even better is that they’ll even brew you a fresh cup of coffee while you browse their beautiful handcrafted items. It’s a touch of hospitality that perfectly encapsulates Portland’s welcoming spirit and makes for a truly pleasant shopping excursion.

Bonus Side Trip: Bend, Oregon

If your Portland itinerary allows for an extra day, I highly recommend taking a scenic day trip to Bend. This charming town is nestled in the heart of Oregon, and the drive from Portland to Bend is an attraction in itself, renowned for its breathtaking natural beauty. You’ll be surrounded by endless stretches of towering green trees, offering a truly immersive experience in the Pacific Northwest wilderness.

Keep an eye out for clear views of Mount Hood majestically peaking out over the horizon. The sight is so awe-inspiring, you’ll undoubtedly want to pause and simply take it all in. Bend itself is a vibrant outdoor paradise, known for its craft breweries and access to stunning natural landscapes.

Boneyard Beer

For beer enthusiasts, a visit to Boneyard Beer is a must. Tucked away in a quaint tasting room, they offer some truly exceptional craft beers. Their Diablo Rojo and Bone-A-Fide were personal favorites, showcasing their mastery of diverse brewing styles. The laid-back atmosphere makes it a perfect stop to sample unique local brews.

Deschutes Brewery Public House

Venturing closer to the heart of Bend, you’ll find the Deschutes Brewery Public House, an ideal spot for a delicious meal paired with fantastic beers. Their taps always feature a delightful selection of brews, and the food menu is expertly crafted to complement the diverse flavors of their beers. After enjoying your meal, take a leisurely stroll around the town center and along the scenic river. This mini-adventure to Bend offers the perfect lazy beer day for all you foodie beer fans, making it absolutely worth the drive.

As you can see, experiencing the full flavor of Portland within 48 hours, with the added bonus of a side trip to Bend for an extra taste of Oregon’s natural beauty and craft beer scene, is not only entirely doable but also incredibly enjoyable. This guide ensures you hit the culinary highlights and cultural gems, creating lasting memories of your Pacific Northwest adventure.

Now, the only question that remains is… where shall our next foodie adventure take us?