A Weekend of Food, Wine & Nightlife in Portland, Oregon

Arrive in Portland by train, car, or plane—all options are easy and convenient. Each of the recommended hotels is centrally located, making it simple to explore the city on foot or via public transit. After checking in, take some time to settle in and take advantage of the perks that come with booking through a Fora advisor to maximize your stay.

For your first dinner, lean fully into a classic Portland experience at one of the city’s beloved food cart pods. Cartopia and Midtown Beer Garden are favorites, but there are others throughout the city. Food carts allow you to sample multiple cuisines in one stop, making them perfect for groups or travelers who love variety. I highly recommend making your own sampler plate from various carts.

After dinner, head out for a casual cocktail crawl. Raven’s Manor is a must-visit—a dark, witchy cocktail bar with immersive décor and theatrical drinks. From there, walk to Ground Kontrol, a two-story arcade bar packed with retro games, pinball, and strong pours. Both are close to several downtown nightlife spots.

If you’re ready to keep the night going, District Nightclub consistently delivers great music and high-energy vibes. Across the street, Xin Ding Dumpling House hides a speakeasy below the restaurant for another uniquely Portland stop. Nearby favorites like Kit Kat Club are also within easy walking distance.

Start your morning slowly—Portland is a coffee city, and exploring local cafés is part of the experience. The city is incredibly walkable, so wander through nearby neighborhoods and pop into a few coffee shops near your hotel. If you’re familiar with Seattle’s coffee culture, this is the perfect opportunity to compare the two (no judgments—I’ll stay neutral).

Next, it’s time to explore Oregon wine. You can stay within the city and visit tasting rooms and wine bars such as Fullerton Wines or Portland Wine Bar, or go deeper with a guided excursion to the Willamette Valley. The valley is one of the top pinot noir regions in the world, and a winery visit offers a beautiful contrast to the city experience. This portion of the day can be tailored based on how relaxed or immersive you want your trip to feel.

For dinner, choose something memorable. Jake’s Grill offers classic Portland charm, while Le Pigeon is a standout for special occasions and one of the city’s most celebrated restaurants. For something more playful and themed, The Love Shack brings a fun, colorful energy to the evening.

Cap the night with cocktails at one of Portland’s standout bars. Multnomah Whiskey Library is iconic for its massive spirits collection, while Scotch Lodge and Below by Botanist offer more intimate, craft-focused experiences. Reservations are strongly recommended for both Scotch Lodge and the Whiskey Library.

Before leaving town, fuel up with one of Portland’s most beloved traditions: donuts. Skip the obvious choices and try local favorites like Sesame Donuts, Pip’s, Blue Star, or the Mini Donut Company. If you’re traveling with others, create a donut sampler and pair it with great coffee before hitting the road.

Portland’s parks and green spaces are another highlight. If time allows, visit the Portland Japanese Garden for a peaceful and scenic send-off, or take a leisurely stroll through one of the city’s many urban parks to soak in the natural beauty.

If your timing aligns—or if there’s a game on—consider stopping by The Sports Bra before departing. As one of the first women’s sports bars in the country, it’s a meaningful, fun spot to grab a bite while supporting women’s athletics.