Oregon’s Portland sprawls over forested hillsides and across the banks of the Willamette and Columbia Rivers, creating a spectacular environment offering unparalleled outdoor access. In the space of a day, you can kayak past downtown, hike an urban volcano, and dine at a world-class restaurant, all without driving far from your beautiful Portland vacation rental. Whether you’re planning an active family vacation or a relaxed weekend full of shopping and cocktails, this lively city has plenty of attractions to keep you busy.

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1. Visit Voodoo Doughnuts

Start your trip to Portland at one of the city’s most iconic attractions: Voodoo Doughnuts. This funky bakery serves up fresh, creative pastries each day. Try house specialties including the Voodoo Doll and the Bacon Maple Bar, or browse the display cases for the latest concoctions. Lines often extend around the block, so arrive early.

2. Dine at the Alder Street Food Truck Pod

Take a break from exploring downtown Portland at the famous Alder Street food truck pod. Here, lines of food trucks gather around the edge of a city block, and hungry diners hang out on tables. Try fish and chips from The Frying Scotsman, or go healthy with a rice bowl from The Whole Bowl. With a huge variety of international cuisines from which to choose, it’s easy to feed everyone in your party.

3. Take a Bike Tour

Experience Portland’s legendary bike culture like a local with a ride down the city’s fantastic trail system. Rent a bike from Pedal Bike Tours, grab a bike-path map, and ride along the Willamette River. When you’re ready to connect to points east, head across the Broadway Bridge. If you’d prefer a gentler introduction, join one of Pedal Bike Tours’ guided rides through the historic downtown area or past the city’s favorite food trucks.

4. Tour the Shanghai Tunnels

Delve into Portland’s fascinating criminal past with a tour of the Portland Shanghai Tunnels, a network of passageways that runs under Chinatown and Old Town. On Portland Walking Tours’ Underground Portland tour, you can explore the tunnels as the guide regales you with tales of kidnappings, criminals, and wild seafaring lore.

5. Wander Through the Portland Japanese Garden

Surround yourself with tranquility and beauty at the Portland Japanese Garden. Walk by the stream in the Strolling Pond Garden, or experience rustic Japanese traditions in the Tea Garden. If you’re interested in the garden’s plants, take one of the excellent public tours. Finish your visit with a cup of traditional tea in the lovely Umami Cafe.

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6. Hike in Forest Park

Find out why local outdoor enthusiasts love Portland with a hike through Forest Park. This stunning urban forest rises above Northwest Portland and offers more than 80 miles of trails. For the best views of the St. Johns Bridge, hike the Ridge Trail. The Tolinda Trail provides a challenging climb, and the Lower Macleay Trail takes you to the park’s famous Stone House.

7. Tour a Brewery

Settle into “beervana” on a tour of Portland’s many breweries. Take a Brewvana tour of breweries in the Pearl District, or visit pubs in neighborhoods such as Mississippi/Williams. With BeerQuest, combine history and beer on a fascinating Haunted Brewery Crawl. Both companies also design private tours catered to the preferences of your group.

8. Shop at Powell’s City of Books

A visit to Powell’s City of Books is a must for any trip to Portland, whether or not you’re in the market for a book. This landmark covers 68,000 square feet, and even has its own app to help you find a specific tome. After you’re done shopping, enjoy the people-watching in the onsite coffee shop.

9. Explore Pittock Mansion

Step into Portland’s past at Pittock Mansion, a turn-of-the-century home with stunning views across the city. Today, the house is a museum; a small admission fee allows you to explore the home’s 23 rooms. Check out the permanent collection of art and antiques, or browse through the rotating exhibitions. The mansion is popular during the Christmas holidays, when spectacular decorations adorn the majestic rooms.

10. Visit the Portland Farmers Market

Get into the downtown vibe at the Portland Farmers Market, which runs from June through September at Pioneer Courthouse Square. Stock the refrigerator in your vacation rental with fresh veggies, bread, and baked goods from local businesses. After, grab a snack, and sit on the square’s steps to enjoy the music and performances.

11. Catch a Performance at the Crystal Ballroom

Spend an evening checking out Portland’s excellent live-music scene at the famous Crystal Ballroom. Kick back with a cocktail, and enjoy popular local and touring bands. Be sure to look up; the venue’s historic ceilings are adorned with colorful murals and vintage lights.

12. Ride the Portland Aerial Tram

Enjoy stunning panoramic views of the city from the Portland Aerial Tram. This scenic ride departs from the base terminal near the Ross Island Bridge and ascends slowly up the hill, providing plenty of time to enjoy the view. Each car features huge windows for easy picture-taking. If you’re traveling with the family, kids aged 6 and under ride free.

13. Visit The Grotto

Hike through a tall pine forest to a secluded cave at The National Sanctuary of Our Sorrowful Mother, which is affectionately known locally as The Grotto. Part Catholic shrine, part botanical garden, The Grotto is a spectacular spot for hiking and reflection. The spot hosts concerts throughout the year, and at Christmas, don’t miss the magical Festival of Lights, when the forest is transformed by thousands of twinkling lights.

14. Watch the Animals at the Oregon Zoo

Watch elephants, rhinos, and tigers at the Oregon Zoo. A winding path connects you to each exhibit, so you can watch giraffes in the Africa area and watch orangutans swing from the trees in the Primate Forest. If you’re visiting with kids, be sure to ride the zoo train.

15. Check Out the World Forestry Center Discovery Museum

Take a fascinating journey through global forests in the World Forestry Center Discovery Museum. As you walk into the awe-inspiring Cascadian-style building, trees soar overhead toward the vaulted ceilings. During your visit, take a water-free raft trip, learn how to use a Timberjack harvester, and work on your smoke-jumping abilities.

 
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