We suspect Goldilocks would feel right at home in Portland. The city is neither too big nor too small, and it’s impossible to run out of things to do. Skyscrapers and evergreen forests coexist here, as do food carts and high-end restaurants. Visitors can stay at a cozy bed-and-breakfast or a swanky downtown hotel, and the city is easily accessible by bike and transit.
Whether you’re new to Portland or just haven’t visited in a while, consider checking out the first-annual Portland Staycation weekend (Sept. 12-15, 2025), a citywide invitation to enjoy special events and discounts downtown and support Oregon’s urban core. Find discounts at some of the city’s most luxe boutique hotels as well as Portland’s award-winning restaurants and diverse shops. Attend a music or art festival; bring the family for a bike ride, a sports game, a museum trip or a stroll across the car-free Tilikum Crossing bridge.
Here’s our just-right guide to Portland for first-timers.
Visit a Block of Books, Enjoy First-Class Dining and Shop Secondhand Goods
Day 1: Downtown Portland
Pick up coffee and a pastry at Courier Coffee Roasters, a tiny shop that roasts its own beans, then cross the street to Powell’s Books, the largest bookstore in the world. Take a lunch break at Måurice, a Nordic-French cafe where you might find strawberry gazpacho or black-pepper cheesecake. Or head to Midtown Beer Garden, home to a wide selection of food carts, or stop at The Flock, one of downtown Portland’s indoor food halls.
Hike or drive up to see the Mt. Hood view from Pittock Mansion, located in the hills of Portland’s 5,200-acre Forest Park — one of the largest urban forests in the country. The Portland Japanese Garden in nearby Washington Park features bonsai, a rock garden, rotating art exhibitions and a tea room.
Downtown is also home to plenty of shopping, including clothing at boutiques Frances May and Machus as well as gender-neutral coveralls at local brand Wildfang. Pick up Japanese home goods at Kiriko, grab souvenirs at Tender Loving Empire and shop for home decor at Woonwinkel.
Sip a cocktail at The Green Room, the open-to-all bar beneath the members-only Multnomah Whiskey Library. For dinner head to Higgins, a farm-to-table restaurant open since 1994, or head a couple miles northwest to Langbaan, a James Beard Award-winning Thai tasting-menu restaurant available by reservation only.
Day 2: Southeast and Central Eastside
Go for a stroll on Mt. Tabor, an extinct volcano boasting views of Mt. Hood and downtown. Nearby at Coquine Market, pick up sandwiches and smoked-almond chocolate chip cookies for a picnic. Farther south, shop on Division Street for secondhand clothing at Artifact Creative Recycle, boutique women’s clothing at Adorn and Wild Cactus, and home goods at Carter + Rose. Stop for a treat at Pinolo Gelato, including seasonal fruit sorbettos in summer.
Later head to the Central Eastside. Scotch Lodge offers a lengthy whiskey selection and playful purple-ube cocktails, along with fried Brie sticks and seaweed-butter pasta. Or grab a seat on the patio at Bauman’s on Oak, where you’ll find over two dozen boozy ciders, many made with apples grown just 35 miles away on Bauman’s Farm, plus a seasonal food menu.
Day 3: North Portland
Start your morning with a chocolate croissant or, if you’re lucky, a flaky kouign amann pastry from JinJu Patisserie, which received the Outstanding Bakery award from the James Beard Foundation in 2025. Walk among the roses at Peninsula Park, then head to the Prost! food-cart pod for lunch or beer and cocktails on North Mississippi Avenue. While you’re on Mississippi, check out clothing at Tigersden Vintage, plus fossils, geodes, pinned bugs and taxidermy at Paxton Gate.
Catch the sunset at nearby Mocks Crest Park, then head back to Mississippi and finish the evening at Lovely’s Fifty Fifty, featuring sourdough-crust pizza with seasonal summer toppings like nectarines. Don’t forget a scoop of their buckwheat-honey toffee ice cream.
Where to Stay: Lodgings With Rental Bikes, Hip Bars and Thermal Soaks
In downtown The Hotel Zags is a stylish hideaway with a gear library of bikes, skateboards, cameras and games available for rent. Or go for a luxury option at The Nines, located near Pioneer Courthouse Square and home to well-regarded restaurants Departure and Urban Farmer.
In Southeast Portland, the Jupiter NEXT hotel is a hip, modern option that’s also home to Hey Love, named the best hotel bar in the country. To experience neighborhoods like a local, try the Evermore or Bluebird guesthouses, sister bed-and-breakfasts in Arts and Crafts-era homes.
Northeast Portland’s CASCADA offers spacious suites and is home to an underground thermal spa with various pools, a cold plunge and an indoor swimming pool. Stay for the Japanese-Portuguese restaurant on-site, Terra Mae. For a quirky experience, check out Tiny Digs Hotel of Tiny Houses, with 12 tiny homes each featuring a distinct personality.
How to Get Around: Car-Free Ways to Navigate the City
Take the MAX Red Line from Portland International Airport and connect via another MAX line or bus, if needed, to get to your lodging. TriMet buses run frequently. The Portland Streetcar is also convenient in downtown and central Portland. Check out TriMet’s trip planner for schedules. For public transit, you don’t need a special app or pass — tap your credit card or use your phone’s mobile wallet.
Bicycling is a great way to see Portland, and the city’s e-bike-sharing program, BIKETOWN, has pick-up and drop-off points all over town. Download the BIKETOWN app and bring your own helmet, or rent bikes from a number of shops in town. Portland is also very walkable. If you’re driving, download the Parking Kitty app ahead of time to make paying for parking easier.
