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Your Ultimate 5-Day Itinerary in Portland for Unforgettable Adventures!

| Last Updated: October 2024

Planning a trip to Portland? We understand that it can be overwhelming with just a few days to explore, but don’t worry—we’ve got you covered! With years of experience living here, my team and I are excited to share our insider tips and insights.

Our guide features a three-day itinerary highlighting all the must-see attractions. If you’re fortunate enough to have five days in Portland, we’ve included a bonus two-day itinerary to help you discover even more of what this incredible city has to offer.

Adventure awaits—let’s go find it!

Day 1 in Portland

Since most of the city’s attractions are located downtown, we are going to explore them on your first day in Portland. On your first day in Portland, dive into a lively blend of attractions mainly found in the city’s central area. 

Mix with the locals and tourists at Pioneer Courthouse Square

Media credits: thesquarepdx

Website
Address: 701 SW 6th Ave
Contact details: +1 503-223-1613
Operating hours: 

  • Monday to Friday: 8:30 AM – 5 PM
  • Saturday to Sunday: Closed

Time to spend: 30 minutes to 1 hour

Start your day at Pioneer Courthouse Square, often dubbed the “living room of Portland.” This bustling plaza is the ideal spot to soak in the city’s ambiance. 

Grab a morning coffee from a nearby café and watch the mix of locals and tourists. With its events and public art installations, the square offers a lively starting point for your adventure.

Enjoy a scenic walk at Tom McCall Waterfront Park

Media credits: traveloregon

Website
Address: 98 SW Naito Pkwy
Contact details: +1 503-823-7529
Operating hours: Monday to Sunday: 5 AM – 12 AM
Time to spend: 30 minutes to 1 hour

Enjoy a scenic walk to Tom McCall Waterfront Park, just a few minutes away from Pioneer Courthouse Square. The park, which stretches along the Willamette River, is a beautiful spot to relax and take in views of the city skyline. 

Whether you choose to walk or bike, this waterfront view is a great place to recharge before continuing your exploration.

Have your lunch at the food cart pod at 10th and Alder

Media credits: portland

Website
Address: 1219 SW Park Ave
Contact details: +1 503-226-2811
Operating hours: 

  • Wednesday to Sunday: 10 AM – 5 PM
  • Monday to Tuesday: Closed

Time to spend: 30 minutes to 1 hour

After immersing yourself in the river, it’s time for lunch at the food cart pod at 10th and Alder. 

Portland is famous for its food cart culture, and this pod offers a diverse array of delicious options. From gourmet tacos to vegan comfort food, there’s something to satisfy every palate. 

Taste some remarkable whiskeys at the Multnomah Whiskey Library

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Website
Address: 1124 SW Alder St
Contact details: +1 503-954-1381
Operating hours: 

  • Tuesday to Thursday: 4 PM – 10 PM
  • Friday to Saturday: 4 PM – 11 PM
  • Sunday to Monday: Closed

Time to spend: 2 to 3 hours

For those seeking a nice meal for dinner and a nightcap in one spot, the Multnomah Whiskey Library is a must-visit destination. Plus, it’s just a short walk from the food cart pod.

This cozy, dimly lit restobar features an impressive selection of whiskies from around the world, complemented by a fantastic menu.

The knowledgeable staff can guide you through tastings, offering insights into the art of whiskey-making. The atmosphere, complete with leather-bound books and vintage decor, also provides the perfect backdrop for unwinding after a busy day.

Day 2 in Portland

One day just isn’t enough to soak up all the cool spots near downtown! So, on your second day, dive deeper and really soak in that Portland vibe. 

Buy some souvenirs at Portland Saturday Market

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Website
Address: 2 SW Naito Pkwy
Contact details: +1 503-222-6072
Operating hours: Saturday: 10 AM – 5 PM
Time to spend: 2 hours

If your second day of adventure falls on a Saturday, make sure to visit the Portland Saturday Market. Located along the scenic waterfront, this open-air market is a lively hub for local artisans, craftspeople, and food vendors. 

You’ll find everything from handmade jewelry to locally sourced foods. Before setting off to your next destination, be sure to grab a coffee and a breakfast pastry from one of the many food stalls.

Have a relaxing walk at Lan Su Chinese Garden

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Website
Address: 239 NW Everett St
Contact details: +1 503-228-8131
Operating hours: 

  • Thursday to Tuesday: 10 AM – 6 PM
  • Wednesday: Closed

Time to spend: 2 hours

After buying some souvenirs, you can continue your morning with a relaxing walk through the Lan Su Chinese Garden. This peaceful spot is a lovely escape from the city. 

The garden’s carefully designed landscapes, calm ponds, and traditional teahouse create a perfect setting for reflection. Take your time exploring this authentic Suzhou-style garden, and if you like, enjoy a cup of tea in the teahouse.

Live your academic dreams at Powell’s City of Books

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Website
Address: 1005 W Burnside St
Contact details: +1 800-878-7323
Operating hours: Monday to Sunday: 10 AM – 9 PM
Time to spend: 30 minutes

Next, head to the Hawthorne District, just a 10-minute drive away. Hawthorne is filled with quirky shops and vintage stores, so you can spend some time exploring these boutiques. Some of them also showcase local craftsmanship. 

Don’t miss the chance to visit the famous Powell’s City of Books, which isn’t too far from the district. It’s just a 10-minute walk from the Lan Su Chinese Garden and the largest independent bookstore in the world. It offers a labyrinth of shelves filled with new and used books. 

Enjoy the performances at Portland Center Stage

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Website
Address: 128 NW 11th Ave
Contact details: +1 503-445-3700
Operating hours: 

  • Tuesday to Sunday: 12 PM – 6 PM
  • Monday: Closed

Time to spend: 2 to 3 hours

As the sun begins to set, head to the Pearl District for an evening at Portland Center Stage. This renowned theater company hosts a variety of performances, from classic plays to contemporary works. 

Check their schedule in advance to secure tickets to a show that piques your interest. The combination of exceptional talent and an intimate venue makes for a memorable theater experience.

Show your dance moves at McMenamins Crystal Ballroom

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Website
Address: 1332 W Burnside St
Contact details: +1 503-384-2511
Operating hours: 

  • Monday to Thursday: 3 PM – 10 PM
  • Friday to Saturday: 11 AM – 12 AM
  • Sunday: 11 AM – 10 PM

Time to spend: 2 to 3 hours

To conclude your day, visit McMenamins Crystal Ballroom that’s located in the vibrant Pearl District. This historic live music venue is known for its vibrant atmosphere and sprung dance floor.

Built in 1914, it features eclectic decor and can accommodate around 1,000 people. The venue hosts a variety of concerts and events. Their menu also offers local beers, wines, and pub fare.

Day 3 in Portland

To explore more of Portland, we’ll focus on the northeast part of the city on the third day.

Spend a serene time at The Grotto

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Website
Address: 8840 NE Skidmore St
Contact details: +1 503-254-7371
Operating hours: Monday to Sunday: 9 AM – 6:30 PM
Time to spend: 2 to 3 hours

Start your day at The Grotto, a serene sanctuary in Northeast Portland known as the National Sanctuary of Our Sorrowful Mother. Established in 1924, it spans over 62 acres and features stunning gardens, peaceful paths, and breathtaking views of the landscape.

The lower level is free to access. It includes a cave that serves as an outdoor cathedral with a replica of Michelangelo’s Pietà surrounded by flowers and candles. 

The upper level is accessible by elevator. It offers beautifully landscaped gardens and stunning views of the Columbia River Valley and Cascade Mountains, including the Marilyn Moyer Meditation Chapel with its glass walls.

Have a hearty meal at the Pine State Biscuits

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Website
Address: 2204 NE Alberta St
Operating hours: 

  • Friday to Sunday: 8 AM – 2 PM
  • Monday to Thursday: Closed

Time to spend: 1 to 1 ½ hour

Just a short drive away from The Grotto, head to Pine State Biscuits, a beloved local eatery famous for its hearty breakfast and brunch options. Here, you can indulge in delicious biscuit sandwiches loaded with your choice of fillings. 

Their “Blueberry Basil Pop Tart” is a delicious treat filled with crushed blueberry compote and basil glaze and finished with a lemon basil oat crumble. This dish balances the sweetness of blueberries with the fresh flavor of basil, making it a refreshing highlight on their menu.

Take pictures with the murals at the Alberta Arts District

Address: Northeast Portland, primarily along NE Alberta Street
Time to spend: 30 to 45 minutes

Portland is known for its murals and vibrant street art, making the Alberta Arts District a must-visit. Here, creativity spills onto the streets, turning every corner into a visual delight with colorful art installations. 

Many of these murals celebrate local culture, history, and social issues. They highlight the community’s diversity and values.

Have dinner at Bye and Bye

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Website
Address: 1011 NE Alberta St
Operating hours: 

  • Monday to Thursday: 12 PM – 12 AM
  • Friday: 12 PM – 2:30 AM
  • Saturday: 10 AM – 2:30 AM
  • Sunday: 10 AM – 12 AM

Time to spend: 1 to 2 hours

As the evening approaches, it’s time to satisfy your appetite at Bye and Bye. It’s a beloved vegan restaurant in the area. Their menu features comfort food with a plant-based twist, ensuring that everyone leaves satisfied.

Enjoy live music at Mississippi Studios

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Website
Address: 3939 N Mississippi Ave
Contact details: +1 503-288-3895
Operating hours: 

  • Sunday to Thursday: 11 AM – 1 AM
  • Friday to Saturday: 11 AM – 2 AM

Time to spend: 2 to 3 hours

After dinner, head over to Mississippi Studios for a night of entertainment. This intimate music venue, housed in a converted church, is known for hosting an array of talented musicians and local acts. 

The warm atmosphere and excellent acoustics make it a perfect spot to enjoy live music. Whether you’re into indie rock, folk, or something more eclectic, you’re sure to find a show that resonates with you.

Day 4 in Portland

On your fourth day in Portland, we’ll explore the top spots in the southern part of the city.

Learn about history at The Oregon Historical Society Museum

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Website
Address: 1200 SW Park Ave
Contact details: +1 503-222-1741
Operating hours: 

  • Monday to Saturday: 10 AM – 5 PM
  • Sunday: 12 PM – 5 PM

Time to spend: 2 hours

After experiencing tranquility at Lan Su, make your way to The Oregon Historical Society Museum. Just a short walk away from the garden, this museum showcases the rich history of Oregon and features engaging exhibits that highlight the state’s cultural heritage. 

From indigenous history to contemporary issues, the museum offers a comprehensive overview that will deepen your understanding of the region.

Try out an Italian cuisine for brunch at The Old Spaghetti Factory

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Website
Address: 715 S Bancroft St
Contact details: +1 503-222-5375
Operating hours: 

  • Sunday to Thursday: 11:30 AM – 9 PM
  • Friday to Saturday: 11:30 AM – 9:30 PM

Time to spend: 2 hours

For brunch, head over to The Old Spaghetti Factory for amazing food. This family-friendly restaurant is renowned for its classic Italian cuisine, served in a warm and inviting atmosphere.

The menu features a popular three-course meal, including fresh bread, soup or salad, and ice cream. Their Spaghetti with Mizithra Cheese and Browned Butter is a distinguished favorite derived from the founder’s family recipe

Engage with science exhibits at the Oregon Museum of Science and Industry

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Website
Address: 1945 SE Water Ave
Contact details: +1 503-797-4000
Operating hours: 

  • Tuesday to Sunday: 9:30 AM – 5:30 PM
  • Monday: Closed

Time to spend: 2 hours

The next stop is the Oregon Museum of Science and Industry (OMSI). Located just south of The Old Spaghetti Factory Restaurant, OMSI features a variety of interactive exhibits for all ages.

You can explore the wonders of space in the planetarium or engage with hands-on science exhibits. If you have children with you, this is a must-visit spot that guarantees hours of fun and learning.

Observe the best city views from the Portland Aerial Tram

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Website
Address: Lower Tram Terminal, 3303 S Bond Ave
Operating hours: 

  • Monday to Friday: 5:30 AM – 9:30 PM
  • Saturday: 9 AM – 5 PM
  • Sunday: Closed

Time to spend: 1 hour

After fueling yourself up, it’s time to take in some of the best views of the city from the Portland Aerial Tram. 

Just a 15-minute walk will get you to the tram station, where you can hop on for a breathtaking ride that takes you high above the Willamette River. It offers panoramic views of the skyline and surrounding mountains. Plus, the tram ride itself is a thrilling experience.

Sing your heart out at the Voicebox Karaoke

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Website
Address: 734 SE 6th Ave
Contact details: +1 503-303-8220
Operating hours: 

  • Monday to Thursday: 4 PM – 12 AM
  • Friday: 4 PM – 2 AM
  • Saturday: 2 PM – 2 AM
  • Sunday: 2 PM – 12 AM

Time to spend: 3 to 4 hours

Finally, end your day with a fun night of karaoke at Voicebox Karaoke. This lively venue offers private rooms where you can belt out your favorite tunes with friends or fellow travelers. 

Whether you’re a seasoned performer or just in it for the laughs, it’s a great way to unwind and celebrate a day well spent in Portland.

Day 5 in Portland

For your last day, here are some additional top spots to explore. Since the Oregon Zoo is a bit farther from the other two locations, we’ve kept the itinerary light to make your day more relaxed. Don’t worry—the last two locations will bring you back toward downtown.

Discover the elephant exhibit at the Oregon Zoo

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Website
Address: 4001 SW Canyon Rd
Contact details: +1 503-226-1561
Operating hours: Monday to Sunday: 9:30 AM – 4:30 PM
Time to spend: 2 to 3 hours

Start your day by visiting the Oregon Zoo. With an impressive collection of animals and a strong commitment to conservation, the zoo offers both educational and entertaining experiences. 

From the Asian elephant exhibit to the polar bears, families and animal lovers alike will enjoy observing these magnificent creatures up close.

Explore the galleries at the Portland Art Museum

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Website
Address: 1219 SW Park Ave
Contact details: +1 503-226-2811
Operating hours: 

  • Wednesday to Sunday: 10 AM – 5 PM
  • Monday to Tuesday: Closed

Time to spend: 2 hours

From the zoo, drive northeast to the Portland Art Museum, just a few blocks away. As one of the oldest art museums in the country, it features an impressive collection that spans various centuries and cultures. 

You’ll find exhibits of Native American art alongside contemporary pieces. Spend a couple of hours exploring the galleries, and be sure to visit the museum store for unique gifts and local artisan products.

Indulge in a seafood delight at Southpark Seafood

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Website
Address: 901 SW Salmon St
Contact details: +1 503-326-1300
Operating hours: 

  • Monday to Friday: 11:30 AM – 8:30 PM
  • Saturday to Sunday: 3 PM – 8:30 PM

Time to spend: 2 hours

To ease your hunger after your museum exploration, Southpark Seafood is just a few-minute walk away. Known for its commitment to fresh and sustainable seafood, the restaurant features a menu that highlights local ingredients and seasonal offerings

You can enjoy a variety of dishes, from classic clam chowder and fish tacos to expertly grilled seafood and creative salads.

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