Portland is one of those cities where you can grab incredible coffee in the morning, hike through a forest in the afternoon, and end the day with amazing food and a local beer. With unique neighborhoods, endless restaurants, and nature just outside the city, Portland is the perfect place for a long weekend getaway.
This three-day itinerary covers the Portland classics, local favorites, and a few spots you won’t want to miss.
Day 1: Classic Portland
Start your trip by checking out some of Portland’s most iconic spots.
Morning: Coffee + Powell’s Books + The Pearl District
Kick things off with coffee from Stumptown Coffee Roasters, Case Study Coffee, or St. Honoré Boulangerie before heading to Powell’s City of Books. This Portland landmark takes up an entire city block and is easy to spend hours exploring. Expect to walk out with a book, a gift, or some fun Powell’s souvenirs.
Afterward, stroll through the Pearl District and browse local shops like Kiriko Made, Tender Loving Empire, Woonwinkel, and MadeHere PDX for unique gifts and locally made goods.
Afternoon: Washington Park
Spend the afternoon exploring Washington Park. Start with the International Rose Test Garden, a free attraction with thousands of roses and some of the best views of downtown Portland and Mt. Hood.
Next, visit the Portland Japanese Garden for peaceful walking paths, koi ponds, waterfalls, and beautiful seasonal scenery.
If you have extra time, stop by Pittock Mansion for one of the best city views or explore the trails at Hoyt Arboretum.
Evening: Northwest Portland
End your day wandering NW 23rd and Nob Hill. This area is full of boutiques, restaurants, bars, and classic Portland spots.
Dinner:
- Andina
- Janken
- St. Jack
- Papa Haydn
- Top Burmese
Drinks:
- Teardrop Lounge
- Pope House Bourbon Lounge
- Palomar
- Side Eye
- Paymaster
Day 2: Columbia River Gorge Day Trip
Portland’s best perk? You can leave the city and be surrounded by waterfalls, mountains, and scenic views within an hour.
Morning: Chase Waterfalls
Start your day at Multnomah Falls, Oregon’s most famous waterfall. The 620-foot waterfall is a must-see, but don’t stop there. Explore some of the nearby trails and viewpoints throughout the Gorge.
Other nearby stops:
- Latourell Falls
- Bridal Veil Falls
- Wahkeena Falls
Remember, Multnomah Falls requires a timed permit during busy seasons, so plan ahead.
Afternoon: Cascade Locks + Hood River
Stop in Cascade Locks for river views and a quick bite before continuing to Hood River.
Cascade Locks favorites:
- Thunder Island Brewing
- Gorges Beer Co.
- Eastwind Drive-In
Hood River is one of Oregon’s best adventure towns, known for breweries, hiking, windsurfing, and incredible views of Mt. Hood.
Where to eat and drink:
- pFriem Family Brewers
- Ferment Brewing
- Double Mountain Brewery
- Solstice Wood Fire Pizza
- Full Sail Brew Pub
If you have extra time, drive the Hood River Fruit Loop for wineries, cideries, orchards, and flower fields.
Don’t miss:
- The Gorge White House
- Stave & Stone Winery
- Mt. Hood Creamery
- Grateful Vineyard
Day 3: Portland Neighborhoods
Spend your last day exploring Portland’s most unique neighborhoods. This is the perfect day for vintage shopping, coffee stops, food carts, and local favorites.
Morning: Southeast Portland
Start in Southeast Portland and explore Hawthorne, Belmont, and Division.
Coffee:
- Heart Coffee Roasters
- Coava Coffee Roasters
- Roseline Coffee
Shopping:
- House of Vintage
- Red Light Clothing Exchange
- Lounge Lizard
- Next Adventure
- Village Merchants
Lunch: Eat Your Way Through SE
Southeast Portland has some of the city’s best food.
Don’t miss:
- Kann
- Magna Kusina
- Hat Yai
- Apizza Scholl’s
- Oma’s Hideaway
- Hawthorne Asylum Food Carts
- Cartopia
Afternoon: Mississippi + Alberta Arts
Finish your Portland neighborhood tour in North Portland. Mississippi and Alberta Arts are packed with colorful murals, local shops, breweries, restaurants, and some of the city’s best hangouts.
Shopping:
- Paxton Gate
- Workshop Vintage
- Tigersden Vintage & Modern
- Salty Teacup
Food and drinks:
- Eem
- Lovely’s Fifty Fifty
- Sweedeedee
- Matt’s BBQ
- StormBreaker Brewing
Final Night in Portland
End your trip with one last great meal and a drink.
Dinner:
- Tusk
- G-Love
- Nostrana
- Le Pigeon
- Dame
Drinks:
- Multnomah Whiskey Library
- Hale Pele
- Victoria Bar
- Bye and Bye
- Revolution Hall Rooftop
Have More Time?
Portland makes a great home base for exploring Oregon. If you have an extra day, add a trip to the Oregon Coast, Mt. Hood, Willamette Valley wine country, or Central Oregon.
Three days is enough to experience Portland’s highlights, but don’t be surprised if you leave already planning your next visit.