Portland city views from Pittock Mansion

3 days in Portland itinerary for an epic weekend (2024)

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Looking for the best 3 days in Portland itinerary for your visit?

You’ve come to the right place! Portland, the largest city in Oregon, is known for its vibrant arts scene, unique attractions, and a delightful fusion of trendy neighborhoods and lush green spaces.

Portland is also a great base for exploring famous places nearby like the Columbia River Gorge and the Oregon Coast.

I recently visited Portland as part of our Oregon road trip itinerary and spent a few days exploring the city and the surrounding regions.

I loved visiting all the downtown Portland attractions like Powell Books and Pittock Mansion, the trendy Portland neighborhoods like Pearl District and NW 23rd Ave. I was amazed at the attractions outside the city like Multnomah Falls and Oregon Coast.

My 3 day Portland itinerary will ensure you see the best sights in downtown Portland and explore its trendy neighborhoods.

You will also get to experience the most famous sights near Portland, like the historic Columbia Gorge and the magnificent Multnomah Falls. Also, no trip to Portland, Oregon, is complete without a visit to the famed Oregon Coast!

So get ready to experience the very best of Portland, the Columbia River Gorge, and the Oregon Coast.

In a hurry and looking for the best recommendations for your Portland Itinerary?

Top Excursions in Portland:

Below are my top recommendations for places to stay in Portland:

➡ If flying into Portland, you will need a rental car. I recommend Discover Cars for the best rates!

3 days in Portland Itinerary

This Portland itinerary is jam-packed with things to do in Portland and nearby, assuming you have three full days in Portland. So ideally, you would have arrived the night before in Portland and be ready to start the next day.

If spending a weekend in Portland or a long weekend, plan to arrive Thursday night so that you have three full days to explore Portland and the surrounding areas.

Overview of Portland itinerary for 3 days

  • Day 1: Explore the sights of Portland downtown – Powell books, Pittock Mansion, International Rose Test Garden, Pearl District, Northwest 23rd Ave
  • Day 2: Experience the Historic Columbia River Gorge and its stops, and visit Multnomah Falls
  • Day 3: Head to the Oregon Coast and enjoy Cannon Beach.

Day 1: Explore Portland City

On Day 1 in Portland, explore the sights and attractions in Portland Downtown.

Some places, like Pittock Mansion and Washington Park, require a car due to their uphill location, while others are walkable and within Portland downtown.

Consider taking a city tour to efficiently cover all the sights during your limited day in Portland. Alternatively, self-guided exploration by car is also an option.

➡ Check rates and availability for this Best of Portland Morning City tour or Best of Portland Afternoon City tour, which covers the top sights. Perfect if you have limited time in Portland!

Pittock Mansion

We started our day in Portland by driving to Pittock Mansion in the morning, around 12 minutes from downtown by car. A small paid parking lot is available outside the mansion.

Pittock Mansion in Portland
Pittock Mansion in Portland

Perched atop a hill, this historic mansion offers the best views of downtown Portland. The mansion’s elegant rooms and exhibits delve into the city’s history. You can take a guided tour of the mansion for a small fee.

Portland city views from Pittock Mansion -  Must visit in any Portland itinerary
Epic Portland city views from Pittock Mansion

Exploring the mansion’s grounds and enjoying downtown views is free. There is a seating area to relax and admire the city views.

Washington Park

Next, we went to Washington Park. Spanning over 400 acres to the west of downtown, Washington Park hosts diverse attractions, including the International Rose Test Garden, Hoyt Arboretum, Portland Japanese Garden, Oregon Zoo, and Oregon Children’s Museum.

Choose one to two attractions that interest you as Washington Park is quite large, and it’s impossible to see everything in a single day. We opted for the International Rose Test Garden, famous in this ‘City of Roses.’

International Rose Test Garden in Portland
International Rose Test Garden in Portland

The Rose garden was huge and spectacular. Thousands of rose varieties bloomed in vibrant colors during July, and the garden and walking paths were well-maintained.

On our next visit to Portland, we plan to explore Hyott Arboretum and its several hiking trails.

Portland Japanese Garden is also really serene and tranquil with its beautiful landscaping and koi ponds. We have a similar Japanese Tea Garden in Golden Gate Park.

Northwest 23rd Avenue

After exploring Washington Park, head to Northwest 23rd Avenue for lunch. Northwest 23rd Avenue, often referred to as “Trendy Third,” is known for its upscale boutiques, cozy cafes, and a mix of local and international restaurants.

The avenue is lined with beautiful tree-lined sidewalks and is great for a leisurely stroll. The street has an inviting atmosphere that captures the essence of Portland’s eclectic culture.

Northwest District in Portland
Northwest District in Portland

The architecture here is a mix of historic buildings and modern designs, giving the area a distinct and appealing vibe.

When it comes to dining options on Northwest 23rd Ave, there are several top-notch restaurants to choose from. Some notable ones include:

Blue Star Donuts – An artisanal donut shop that specializes in creative flavors and high-quality ingredients. It’s a favorite among donut lovers.

Papa Haydn – European-style cafe serving sandwiches, salads, entrees, and scrumptious desserts.

Grassa – Italian restaurant serving handmade pasta dishes! Some of the best pasta you have ever eaten!

Thai Bloom – Delicious Thai cuisine with curries, noodles, and rice dishes. We tried the Pad Thai, pineapple fried rice, and yellow curry, and everything was really good.

Matador NW Portland – Mexican restaurant and bar serving Mexican dishes and cocktails.

Bamboo Sushi – A sustainable and eco-friendly sushi restaurant that offers a delectable selection of fresh and responsibly sourced seafood.

Salt & Straw – A renowned ice cream parlor known for its innovative flavors and use of locally sourced ingredients. Expect creative combinations that cater to a variety of tastes.

Pearl District

Visiting the Pearl District offers a glimpse into Portland’s dynamic urban lifestyle and creative spirit. It’s where you can savor gourmet food and coffee, explore art galleries, and get a glimpse of the city’s upscale urban living.

Formerly an industrial area, it’s now known for its chic galleries, stylish boutiques, and a plethora of eateries.

Sidewalk in Portland lined with shops and trees

The neighborhood is a hub for contemporary art, with numerous galleries showcasing local and international talent. In the monthly art event called ‘The First Thursday Art Walk, ‘ galleries open their doors to art enthusiasts.

The Pearl District is home to several exceptional cafes and restaurants catering to diverse cuisines. A few top choices include:

Stumptown Coffee Roasters – A Portland institution passionate about crafting excellent coffee. Try the cold brew coffee here. It’s really good!

Caffe Umbria – A cozy Italian-style coffee shop known for its quality espresso and yummy pastries. A nice place to people-watch as well!

Andina – A Peruvian restaurant offering a fusion of traditional and modern dishes and a diverse cocktail menu.

Mediterranean Exploration Company – An upscale Mediterranean restaurant serving Middle Eastern dishes. It is a great place to eat with family and friends and share multiple dishes.

Oven and Shaker – Pizzeria serving great wood-fired artisanal pizzas and craft cocktails.

Powell’s City of Books

A must-visit in downtown Portland, Powell’s City of Books is among the world’s largest bookstores. My family spent a great amount of time here, and we bought several books to take home!

Powells Books Store in Portland
Powells Books Store in Portland

The bookstore spans an entire city block, housing a staggering collection of new and used books across multiple floors and color-coded rooms. They have a map to navigate the store! The third-floor Rare Books room is impressive with really unique and expensive books.

Aisles filled with books in Powells book store in Portland
Powells book store in Portland

The diverse book selection caters to every interest and genre, from rare editions to contemporary bestsellers. The cozy reading nooks and friendly staff make it a bibliophile’s paradise.

The Shake Shack restaurant opposite Powell’s is a great place to grab one of their gourmet smoothies and delicious burgers and fries.

Waterfront Park

In the evening, take a leisurely walk along the Willamette River waterfront, enjoying scenic city views and bridges. This scenic park offers a tranquil escape from the city’s hustle and bustle with its sprawling green spaces, tree-lined paths, and stunning riverfront views.

The Waterfront Park Trail starts at Burnside Bridge’s south end, ideal for strolling, cycling, or jogging along the river. The park hosts various festivals and events throughout the year.

Portland Saturday Market is a popular event on the weekends with local vendors selling handmade arts and crafts and food items.

Note: Downtown Portland has a noticeable homeless population, particularly near the waterfront. Daytime exploration generally feels safe.

➡ Check rates and availability for this 2.5-hour Dinner Cruise on Willamette River with live piano music and great food. Enjoy the city lights and views as you cruise on the Willamette River.

Day 2: Columbia Gorge, Multnomah Falls, Hood River

No trip to Portland is complete without a visit to the iconic Multnomah Falls and driving on the historic Columbia Gorge Highway.

On Day 2 in our Portland itinerary, we will venture out of the city, explore the Historic Columbia River Highway and its stops, and later visit the windsurfing town of Hood River.

If you are not planning to rent a car, you can also book a half-day tour from Portland to Columbia Gorge and the waterfalls.

➡ Check rates and availability for this highly rated Half-Day Columbia River Gorge and Waterfall Hiking Tour – Visit Multnomah Falls and other waterfalls and vista points on the historic Columbia Gorge Highway.

Historic Columbia River Highway Scenic Drive

Oregon is famous for its iconic waterfalls, and you will come across several of them on the Columbia River Hwy scenic drive.

This drive winds through Oregon’s Columbia River Gorge with stunning views of waterfalls, cliffs, and the Columbia River. This drive reminded me of the Road to Hana drive in Maui!

Only around 30 minutes from Portland, the historic highway runs alongside I-84 E, with several spectacular waterfalls and viewpoints. Take exit 22 on I-84 E and follow the NE Corbett Hill Rd to Historic Columbia River Hwy.

Below are the must-see stops on the historic Columbia River Hwy:

Portland Women’s Forum State Scenic Viewpoint

Named after the Portland Women’s Forum group that advocated for Gorge preservation, this viewpoint offers panoramic scenery of the Columbia River Gorge.

View of Columbia River and Vista House from Portland Women's Form viewpoint
View of Columbia River and Vista House from Portland Women’s Form viewpoint

From here, you will see the Vista House in the distance. We had a clear sky with incredible views on the day of our visit. I feel the picture above is postcard-perfect!

Vista House at Crown Point

Perched on Crown Point, the Vista House is a beautifully designed historic observatory that provides panoramic views of the Columbia River Gorge. It’s a perfect place to take in the awe-inspiring scenery and photos.

Vista House at Crown Point near Portland
Vista House at Crown Point on Columbia River Hwy

Latourell Falls

One of the first waterfalls you’ll encounter, Latourell Falls features a striking columnar basalt formation and a picturesque plunge into a pool below. A short 1-mile hike takes you to the viewpoint for an up-close look.

Bridal Veil Falls

A short hike from the highway leads to Bridal Veil Falls, where water cascades gracefully over a cliff, resembling a bridal veil.

Multnomah Falls

The most famous waterfall in the area, Multnomah Falls, is a two-tiered waterfall that drops 635 feet.

Cascading gracefully down a lush, forested cliffside in the heart of the Columbia River Gorge, this two-tiered waterfall is an iconic symbol of the Pacific Northwest’s breathtaking landscapes.

Multnomah Falls in Columbia River Gorge, Oregon
Multnomah Falls in Columbia River Gorge, Oregon

The lower tier has a large viewing platform. A short trail from here leads to Benson Bridge for a closer look at the upper falls.

Expect large crowds at Multnomah Falls, especially in summer. For I-84 parking during the busy summer months of May to September, you need to make a reservation on Recreation.gov. The historic highway’s parking lot doesn’t need a permit but is much smaller.

Note: The two parking lots at I-84 and Columbia River Hwy aren’t directly connected, and you will have to get on I-84 to access the larger I-84 parking lot.

Hood River

Nestled in the heart of the Columbia River Gorge, Hood River is a charming town that offers breathtaking views of the river, lush landscapes, and the iconic Mount Hood.

Hood River Waterfront Park
Hood River Waterfront Park

Hood River is conveniently located about an hour from Portland and around 30 minutes east of Multnomah Falls via I-84 E. The drive from Portland to Hood River is very scenic along the Columbia River.

Hood River is known for windsurfing, kiteboarding, good food, shopping, and scenic river views. Whether you have a few hours or plan to stay overnight, there’s something for everyone.

Top Activities in Hood River:

Hood River Fruit Loop: This self-guided tour lets you explore charming orchards and farm stands. During harvest season, you can enjoy fresh produce, artisan foods, and U-pick experiences.

Hood River Lavender Farm: A picturesque stop where you can pick your own lavender bouquet and find various lavender products like oils, body items, and edible lavender.

Hood River Lavender Farm
Hood River Lavender Farm

Hood River Waterfront Park: Situated by the Columbia River, it’s an ideal spot for picnics, kite flying, or just relaxing by the water. The park provides breathtaking river views and pleasant walks along the water.

Windsurfing and Kiteboarding: Hood River draws windsurfing and kiteboarding enthusiasts due to the consistent winds and stunning Columbia River Gorge views. It’s captivating to watch the action from the waterfront park.

Local Wineries: Explore the Columbia Gorge AVA’s wineries, known for exceptional wines like Pinot Noir and whites. A wine tour will let you sample these offerings while enjoying the scenic surroundings.

Craft Breweries: Hood River boasts a lively craft beer scene with several breweries. You can unwind on their patios, savor seasonal brews, and soak in the town’s relaxed atmosphere.

Downtown Hood River: Hood River’s downtown area is filled with unique boutiques, galleries, and craft stores. You can find locally made goods, artwork, souvenirs, and restaurants.

Whether you’re passing through or planning a longer stay, Hood River promises a mix of outdoor activities, great food, and vibrant local culture.

If you have an extra day, Hood River is also a great place for an overnight or weekend stay.

Columbia Gorge Hotel and Spa is a wonderful hotel right next to the river. It has a spa, golf course, and a restaurant you can enjoy. Choose a room that looks out over the Columbia River!

Day 3: Oregon Coast

On your Day 3 in Portland, head to the famed Oregon Coast. Cannon Beach on the Oregon Coast is only a 1.5-hour drive from Portland, making it great for a day trip from Portland.

Oregon Coast

Below are your three options for a day trip to the Oregon Coast from Portland:

  1. Drive to Canon Beach (1.5 hrs) and spend the rest of the day at the beach. This option has the least driving and more fun time at the beach.
  2. From Canon Beach, drive south to Tillamook (1 Hour) and visit the Tillamook Creamery.
  3. From Canon Beach, drive north to Astoria (40 minutes) and explore Ecola State Park along the way.

No matter which day trip you pick from the above three, you will be in awe of the stunning Oregon coast!

Oregon Coast is a great trip in any season. Visiting the Oregon Coast during winter is a whole different experience, with dramatic coastal storms and whale-watching opportunities.

Keep in mind that while these are some highlights, there’s much more to discover along the beautiful Oregon coast, and it would require at least a 3-day trip to explore the entire Oregon Coast from north to south.

Alternatively, if you do not wish to rent a car, you can take a full-day tour to the Oregon Coast from Portland.

➡ Check rates and availability for this highly rated small group Oregon Coast tour from Portland that takes you to Canon Beach and Haystack Rock and explore other coast attractions.

Cannon Beach

Cannon Beach is a scenic coastal town famous for Haystack Rock, a towering sea stack that graces the shoreline. Cannon Beach is one of the best places to visit on the Oregon Coast.

The beach is wide and has soft sand, so it’s great for walking, beachcombing, and watching beautiful sunsets. We visited a Wednesday morning in July, and there were many people on the beach.

Haystack Rock on Canon Beach
Haystack Rock on Canon Beach

It was a bit windy, but it was okay for us since we’re used to cold beaches in Northern California. Remember to wear layers of clothes for your trip along the Oregon Coast!

Wayfarer Restaurant & Lounge is right by the beach, where you can get delicious seafood for lunch.

If you need a place to stay, the Surfsand Resort is an excellent resort for families, and it’s right on the beach. They have comfy rooms and family-friendly amenities.

Tillamook Creamery

Driving from Cannon Beach to Tillamook Creamery takes about an hour and is a scenic journey along the Oregon coast. The route takes you through lush landscapes and charming coastal towns.

Tillamook Creamery building
Tillamook Creamery building

The Tillamook facility is enormous. It was very crowded on the day we visited. It was a Wednesday afternoon!

Upon arriving at the creamery, you’re greeted with a modern facility where you can learn about the cheese-making process, sample various cheeses, and enjoy freshly made ice cream.

Tillamook Cheese Factory on Oregon Coast
Tillamook Cheese Factory on Oregon Coast

The creamery offers interactive exhibits, a gift shop with local products, and a viewing area to see cheese production.

They have self-guided tours as well as paid tours. The cafeteria has some great lunch options. We tried the deep-dish pizza, which was great!

Tillamook Ice cream
Tillamook Ice cream

Make sure to purchase some of their delicious ice cream. They have a lot of unique flavors here, not sold in stores!

Ecola State Park

Just north of Cannon Beach, Ecola State Park offers scenic viewpoints, forested trails, and rugged coastal panoramas. The Ecola Point viewpoint provides breathtaking vistas of the coastline.

You can stop here to take in some dramatic views of Cannon Beach and the coastline, or you can make it a longer stop and do a hike.

View of beach and ocean on Oregon Coast

The Clatsop Loop Trail is a moderate 2.6-mile loop hike in Ecola State Park, Oregon, and is very popular. It forms a loop through the coastal forest, offering glimpses of the ocean. You will need around 2 hours for this hike.


Astoria is a small coastal town at the very northern end of the Oregon Coast, near the Columbia River. Astoria is around 40-minute drive north of Canon Beach.

Below are the top things to do in Astoria:

Columbia River Maritime Museum: Discover maritime history through exhibits and artifacts. Learn about shipwrecks, navigation, and the region’s seafaring heritage.

Astoria Column: Climb to the top of this tower for panoramic views of the town, Columbia River, and surrounding landscape. The column also features intricate murals depicting local history.

Astoria downtown: Stroll through Astoria’s quaint streets lined with Victorian houses, art galleries, and souvenir shops selling art, crafts, and specialty items. The town’s architecture and atmosphere offer a distinctive charm.

Seafood Dining: Indulge in fresh seafood at local eateries. Astoria’s coastal location ensures a delectable array of seafood options, from fish and chips to seafood chowder.

Cannery Pier Hotel & Spa is an excellent place to stay right on the Pier if you would like to spend a night in Astoria.

More Things to Do in Portland

If you have time, below are some more things to explore in Portland on your visit:

Pioneer Courthouse Square: Known as “Portland’s Living Room,” this central plaza hosts events and serves as a hub for people-watching, performances, and gatherings.

Pioneer Courthouse Square in Portland
Pioneer Courthouse Square in Portland

Food Truck Pods: Indulge in Portland’s renowned food truck scene, offering diverse cuisines and creative flavors in a casual outdoor setting. There are several food cart pods in Portland. The notable ones are at Pioneer Courthouse Square, Portland State University, Third Avenue, and Fifth Avenue. Stretch the Noodle is a very popular hand-made noodle food cart in the Fifth Avenue food cart pod.

Voodoo Doughnut: Satisfy your sweet tooth with a visit to this famous doughnut shop, known for its unique and whimsical creations.

Portland Art Museum: Immerse yourself in the city’s art scene by visiting this museum featuring an extensive collection of American, European, and Native American art.

Oregon Museum of Science and Industry (OMSI): An interactive and educational science museum offering hands-on exhibits for all ages.

Craft Breweries: Experience the craft beer culture by visiting some of Portland’s renowned breweries and tasting rooms, known for their diverse and innovative brews.

Hiking in Forest Park: Discover the urban wilderness of Forest Park with its network of hiking trails, providing a serene escape from the city hustle.

Willamette Valley Wine Tour: Take a wine tour from Portland and visit some of the famous wineries and try pinots, chardonnay, and more.

➡ Check rates and availability for this highly rated small group Willamette Valley Wine Tour with a picnic lunch.

Where to Stay in Portland

With just 3 days in Portland, I recommend staying in downtown Portland so that you have more time to explore the city. There are some nice areas in Portland downtown that are quite safe to stay in.

Below are some great recommendations for your stay in Portland:

Downtown Portland

Hyatt Centric Downtown Portland – Situated in the heart of the city, the Hyatt Centric offers a convenient stay with modern amenities and easy access to downtown attractions. We stayed here during our visit to Portland and cannot recommend it enough!

Hills View from our room in Hyatt Centric
Hills View from our room in Hyatt Centric

It was the perfect location to explore all the top sights in downtown Portland. The hotel is new and very modern and has a restaurant onsite. It also has valet parking privileges for a daily rate.

But what we loved about this hotel is the excellent and friendly staff. Everyone we met was awesome, with excellent customer service. We got a bed and breakfast rate and loved the made-to-order breakfast at the restaurant.

➡ Check rates and availability for Hyatt Centric Downtown Portland

Northwest District

Inn at Northrup Station is a great mid-range all-suite hotel in the trendy Northwest District of Portland. The hotel has free parking and complimentary breakfast.

Walk to all the restaurants and stores on NW 23rd Avenue and to the metro station.

➡ Check rates and availability for Inn at Northrup Station

Pearl District

Canopy by Hilton Portland Pearl District is located in the upscale and urban Peral District with trendy cafes and amazing restaurants. This modern hotel has valet parking and a restaurant onsite.

➡ Check rates and availability for
Canopy by Hilton Portland Pearl District

Travel Tips for Visiting Portland

The travel tips below will help you plan and make the most of your visit to Portland!

When is the best time to visit Portland?

The best time to visit Portland is during the mild and dry months of summer, from June to September. This is when you’ll experience pleasant weather, vibrant outdoor events, and the blooming of the city’s iconic rose gardens.

September is a great month to visit, with fewer tourists compared to the summer months, and the weather is still pleasant.

How many days to spend in Portland, Oregon?

Spending around 3 to 4 days in Portland would allow you to explore the city’s main attractions, enjoy its diverse culinary scene, and possibly take day trips to nearby natural wonders.

How to get to Portland, Oregon?

Portland is accessible by air through Portland International Airport (PDX), which serves both domestic and international flights. It’s also well-connected by road and rail.

How to get around Portland, Oregon?

Portland has an efficient public transportation system, including light rail (MAX), buses, and streetcars. Biking is popular too, thanks to its bike-friendly infrastructure. Ride-sharing services and walking are also convenient options for getting around the city.

Portland Streetcar
Portland Streetcar

You will need a rental car if you wish to take day trips from Portland to Multnomah Falls, Columbia River Gorge, or Oregon Coast. I recommend checking out Discover Cars for the best rates!

Alternatively, you can also take day tours from Portland to nearby attractions.

What to pack for a trip to Portland?

Pack comfortable walking shoes, layers for changing weather, a rain jacket or umbrella, and a reusable water bottle. Don’t forget to bring your camera, as there are plenty of picturesque spots to capture.

Is Portland worth visiting?

Absolutely, Portland is worth visiting! With its unique blend of urban culture, trendy neighborhoods like Pearl District and Northwest District, culinary delights, lush green spaces like Washington Park, and easy access to natural attractions nearby like the Oregon Coast and Columbia River Gorge, Portland offers a well-rounded and memorable travel experience.

Is Portland safe?

Portland is generally considered safe for visitors, but it’s important to be aware of certain aspects.

One noticeable concern is the homeless population, which is visible in parts of the city. While most homeless individuals are not a threat, exercising caution and avoiding confrontations is recommended.

Certain areas of the city, such as Old Town/Chinatown and some parts of East Portland, may have higher instances of homelessness and associated challenges.

While these areas might be best approached with caution, it’s important to note that the majority of Portland remains safe and welcoming for tourists.

We stayed in Portland downtown and felt very comfortable exploring it during the day. Overall, staying vigilant and adhering to common safety practices is advisable when exploring any urban area.

Final Takeaways: Portland Itinerary for 3 days

In conclusion, this 3-day Portland itinerary offers a balanced mix of city exploration and captivating day trips.

From uncovering the city’s attractions to venturing to Multnomah Falls, Columbia River Highway, Hood River, and the Oregon coast, this itinerary ensures a well-rounded experience of the diverse beauty and attractions that Portland and its surrounding areas have to offer.

I hope you have a great time exploring Portland and and its breathtaking surroundings!

More about Portland and Oregon

Make sure to read other posts from my Portland and Oregon series!