Portland, OR in 3 days

Portland, OR is the perfect spot for a long weekend getaway. Whether you’re traveling with family, girlfriends, your partner, or even solo, the city offers a mix of fun, relaxation, and just the right touch of ‘weird’ to keep things interesting.

Recommended Accommodations.

These Portland hotels have the charm, history, and prime locations you need for a perfect getaway.

1. The Porter Hotel | A refined, modern choice in the Pearl District with upscale rooms, scenic views, and a stylish atmosphere that blends city chic with comfort.

2. McMenamins Crystal Hotel | A rock ‘n’ roll–inspired stay housed in the historic Crystal Ballroom building. Playfully decorated rooms, rotating live events, and a unique saltwater soaking pool make this one unforgettable experience.

3. Hotel Dossier | A chic boutique stay right in downtown Portland, perfect if you want something stylish, central, and just a little indulgent.

The best time to travel to Portland is dependent on what you plan to do and see.

• Late Spring (May–June): Mild weather, blooming gardens, and fewer crowds.

• Summer (July–August): Warm, sunny, and perfect for outdoor adventures; but it’s peak tourist season.

• Early Fall (September–October): Gorgeous foliage, harvest season at nearby wineries, and comfortable temps.

Let’s talk food because Portland has a lot to offer!

From food carts and farm-to-table restaurants to craft breweries and donut shops, the city is a foodie’s dream. Here are a few of our favorite’s worth adding to your list.

Some must try Portland Eateries, including those iconic stops:

• Voodoo Doughnut Famous for its quirky creations (like the Bacon Maple Bar). A must-visit at least once.

• Salt & Straw Small-batch ice cream with inventive, seasonal flavors (olive oil, honey lavender, or even Thanksgiving turkey in November!).

• Stumptown Coffee Roasters The Portland coffee scene is huge, and this is the OG.

• The Screen Door with two locations (Eastside and Pearl District) has the best breakfast in town! Food that will wake your taste buds and have you saying “well, bless your heart”!

• Fogo De Chao A Brazilian Steakhouse with exceptional reviews!

• Eem Thai BBQ, a favorite for the locals.

• No trip to Portland is complete without a stop (or three) at the city’s famous food cart pods. Unlike typical street food, these pods are clusters of carts serving everything from Thai and Mexican to vegan BBQ and gourmet grilled cheese. It’s the perfect way to taste Portland’s creativity in one spot.

Portland 3-Day Itinerary

📍 Day 1: Explore Downtown + Pearl District

• Pioneer Courthouse Square Known as Portland’s “living room,” often with events or live music.

• Powell’s City of Books The world’s largest independent bookstore. Plan to get lost in here. Don’t miss the Rare Book Room!

• Pearl District Art galleries, boutiques, and breweries. Great spot for dinner and drinks.

📍 Day 2: Gardens, Animals & Neighborhood Vibes

• International Rose Test Garden Over 10,000 roses in bloom (best late spring–summer).

• Portland Japanese Garden Peaceful, beautifully designed, and considered one of the best outside Japan.

• Oregon Zoo is home to more than 2,000 animals representing over 200 species, from elephants and lions to penguins and sea otters, making this a great family attraction.

• Alberta Arts District Colorful murals, unique shops, and great food trucks. Join a food tour.

• Mississippi Avenue Perfect for live music and local bars at night.

📍 Day 3: Day Trips + Outdoors

• Columbia River Gorge Just 30 minutes outside the city, home to stunning waterfalls like Multnomah Falls.

• Mt. Hood Year-round beauty, from hiking in summer to skiing in winter.

• Willamette Valley Wineries Sample Oregon’s famous pinot noirs at nearby vineyards.

Quick tip:

The sweet spot is late spring or early fall for great weather without big crowds.