Oregon Road Trip: Best 2-Week Scenic Photography Itinerary

Oregon is an incredible place. From its lush forests to the sandy shores, this state is full of outdoor adventures and interesting history. One of the best Oregon vacation ideas is to explore the state on an Oregon road trip!

There are so many Oregon attractions and places to visit that planning an epic journey may be a challenge.

Oregon Road Trip

However, this Oregon road trip itinerary has done the planning for you. It includes not only the best places to stop, but also some of Oregon’s top photographic attractions. 

So get scrolling to discover the best road trip in Oregon!

get the free road trip planner
This site contains affiliate links which means WE may receive commissions for purchases made through these links. We only provide links to products we actually use and/or wholeheartedly recommend! As an Amazon Associate, we earn from qualifying purchases. Read the full Disclosure Policy.

What to Pack for a Trip to Oregon

  • Rain jacket – always be prepared for rain while you’re visiting Oregon, especially near the coast. 
  • Hiking shoes – If you’ll be exploring any hiking trails in Oregon, we recommend hiking shoes instead of sandals. After the umpteenth time of getting rocks out of the sandals, you’ll thank us!
  • Hiking socks – Darn Tough socks help prevent blisters, keep your feet dry, and are guaranteed to last. 
  • Water shoes – You’ll want shoes that are made to get wet AND protect your feet from the rocks. If you’ll be visiting the coastal beaches and tidepools, pack water shoes.
  • Sunscreen 
  • Refillable water bottle
  • Healthy snacks
  • Camera Gear Checklist for Travel Photography

Family Travel Resources

Grab the free printable Oregon Bucket List Packet for even more things to see, do, and taste in this cool state!

Oregon Bucket List Packet optin

Oregon Road Trip Map 

Have a look at this map so you can see where you’ll be traveling during your Oregon road trip. 

Your Oregon Road Trip Itinerary 

This road trip from Portland goes past some of the most scenic Oregon photography locations. From lush forests, mountains, and lakes to stunning coastal cliffs and beaches, you’ll constantly be amazed by the natural wonders. 

So buckle up and make sure you have your travel camera at the ready for your epic road trip through Oregon.

Day 1: Start Your Oregon Trip in Portland

Also known as the City of Roses to some and Bridgetown to others, Portland has a unique energy. This friendly city is laid back and full of interesting people who enjoy living the good life.

If you’re looking to do anything fun while here, know that it’s going to involve either good food, relaxation, and nature. 

Eat your heart out with Portland’s outstanding Food Cart Scene. 

Head to the Portland Japanese Garden for some peace and tranquillity. Otherwise, you can explore the Lan Su Chinese Garden. A spectacular garden that’s been fashioned in true Ming Dynasty style. 

The International Rose Test Garden has an incredible array of over 600 rose bush varieties. 

Multnomah Falls, Oregon’s tallest waterfall, is only 30 minutes from Portland. This is a must-see attraction.  

Day 2: Drive through to Hood River (drive time 1 hour from Portland)

Road trip from Portland to Hood River, a vibrant town located along the Columbia River Gorge. On this Oregon scenic byway, you’ll find plenty of spectacular viewpoints and waterfalls. You’ll want to photograph the river and waterfalls

Photo Credit: Ghe Buhay

Drive up to Vista House and enjoy the view from Crown Point. Or hope on a bicycle and discover some incredible wineries.

Days 3&4: Mt. Hood National Forest

Come unearth the natural wonders of this national forest. The area offers visitors the chance to appreciate its hot springs, lakes, waterfalls, and glaciers. Its inhabitants include an abundance of flora and fauna. 

In the Oregon summer, travelers spend their time here hiking, climbing, and camping. In the winter, the snow-capped slopes beckon skiers and snowboarders. 

However, the greatest draw to this scenic national park is that of Mt. Hood. This 11,240-foot high giant is not only Oregon’s tallest mountain but also a dormant volcano.  

Day 5&6: Bend

This sunny town in central Oregon is surrounded by drier, more rugged terrain. With the Deschutes River running through the town and several mountains surrounding it, Bend is an adventurer’s paradise.  

Explore Newberry National Volcanic Monument, a must-see volcanic site. Enjoy panoramic views of Mt. Bachelor, the Three Sisters, and Broken Top. Or stroll along the paths to the lava field which was used as a training spot for NASA astronauts in the mid-1960s. 

It’s easy to understand why Smith Rock State Park is one of the seven wonders of Oregon. The towering rock spires and mountains make for excellent climbing and bouldering sites. You can also hike one of the many trails and try to spot golden eagles and river otters. 

Day 7 & 8: Crater Lake National Park

Now at the midpoint of your trip, you’ll get to see one of the best places to visit in Oregon. This pristine, icy-blue lake formed over 7000 years ago and is one of the deepest lakes in the United States. 

If you’re in Oregon in the summer, you’ll be able to take the ferry out to Wizard Island. In the winter there are plenty of snowy slopes waiting for avid skiers to enjoy. 

This natural wonder continues to attract sightseers, photographers, and artists who try to capture its beauty. Read this guide on basic photography techniques to make sure you get the best landscape photographs of this gorgeous lake. 

Day 9: Brookings 

Brookings, your first coastal stop on your road trip from Portland. The greatest Oregon attraction to see here is the postcard-perfect Samuel H. Boardman Scenic Corridor.

The 12 miles of Oregon coastline here are named after the Oregon State Park’s late superintendent who worked tirelessly to conserve this land. 

Anyone who loves photographing the coast, or nature in general, has to go to the iconic Natural Bridges. Whaleshead Beach is just 7 miles north of Brookings. Just off this stretch of beach is a sea stack that looks like a whale’s head – hence the beach’s name. 

When visiting these two spots, you’ll want to consider taking some waterproof hiking boots as well as a rain jacket with you. 

Day 10: Winchester Bay

Stop off at this coastal town in the Dunes National Recreation Area where you can go see the 19th century Umpqua River Lighthouse. 

The windswept sands of the Oregon Dunes National Recreation Area are one of the most popular attractions here. Explore these dunes and get an adrenaline kick by renting some four-wheel bikes.

Spend some time hunting for crabs and catching fish. Or relax on the beach and try to spot some whales. 

Day 11: Florence (33 minutes drive from Winchester Bay) and Newport (1.5 hours drive from Florence)

During your Oregon trip to Newport, be sure to stop off in Florence and photograph the impressive Heceta Head Lighthouse. 

There are plenty of things to do in Newport. You can learn about marine wildlife at the Oregon Coast Aquarium or head down to Nye Beach to watch a spectacular sunset over the ocean.

You can also visit Oregon’s tallest lighthouse in Yaquina Head Marine Gardens. Here, you can explore tidal pools, look out for whales, and sit amongst the colorful wildflowers. 

Day 12 & 13: Seaside (2.5 hours drive) and Astoria

Before you reach Astoria, stop off in the quaint village of Seaside. Spend an afternoon walking along the promenade and having a bite to eat at one of the many lovely restaurants. 

Cannon Beach is just 15 minutes south of Seaside and is home to the fascinating Haystack Rock. 

Astoria itself is located at the mouth of the Columbia River and is one of the oldest American settlements on the western side of the Rocky Mountains. 

Take a gander around town and see the old Victorian homes or visit the Captain George Flavel House Museum. The Astoria Column is a monument in honor of the first settlers of Astoria and attracts many tourists. 

Day 14: Back to Portland (1 hour 45 minutes  drive from Astoria)

You’ll finish off your road trip in Oregon back in Portland. If there are attractions and places you didn’t get to see at the start, now’s the time to do it. For anyone traveling with their kids, be sure to read this post on things to do in Portland with your kids

If you loved your time on your road trip in Oregon and want to stay a little longer, consider this Willamette Valley Wine Tasting Tour from Portland

Final thoughts on this Oregon Road Trip

From the breathtaking waterfalls of the Columbia River Gorge to the coastal cliffs and sandy shores, Oregon has some alluring natural attractions.

The best way to see this state is in your own time on a road trip. There are plenty of Oregon road trip ideas out there, but this one has included as many of the best attractions as possible in two weeks.  

So, what are you waiting for? Buckle up, get your travel photography gear ready – Oregon is waiting for you.

Find Oregon Travel Guides at Amazon:

Oregon guides
get the free travel planner

Similar Posts


  1. Hello. Thank you very much for the itinerary. It is really going to help me with my planning.

    I wanted to know if you could suggest which towns to stay in airbnbs. I have been looking at some expensive options but I don’t know if staying in a town a bit less known would be a better and cheaper option.

    I am traveling with my 4 kids (13, 12 , 10 and 4!) and my wife.

    Thank you for your help!

    1. Hi Alex! Finding Airbnb or VRBO vacation rentals in Oregon can be tricky, especially along the coast. The prices go up during the peak travel seasons. And you’ll find higher prices for rentals close to the beach or the attractions in the area. If you don’t mind a bit of a drive to get to those things, then expand your search farther away from the main tourist areas. Our biggest tip for vacation rentals is to read the reviews and comments. AND we now only book rentals that allow full cancellations a few weeks prior to the trip because you never know anymore, right!? We’re finding there aren’t many “cheap” areas in Oregon anymore, so find the location and amenities that work best for your family and just enjoy the trip!

Leave a Reply

Your email address will not be published. Required fields are marked *