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Oregon is a beautiful and underrated state. If you want to plan an epic adventure, you’re in luck. This post will help you plan an epic 4-7 day Oregon road trip itinerary to ensure that you have an amazing trip.

Planning your Oregon Road Trip Itinerary

Likely the easiest way to get to Oregon is to fly into Portland, Oregon (airport code: PDX). However there are other smaller airports if you want to direct your trip towards the center or southern parts of the state. If you plan to stay in the south, fly into Medford, Oregon (airport code: MFR). If you plan to stay in the center of the state, fly into Redmond, Oregon (airport code: RDM). This post will assume you plan to center your Oregon road trip itinerary in Portland but feel free to modify it as you find flights.

Unless you are traveling to Portland and planning to stay only in that area, getting a rental car is recommended in order to see the best places in Oregon. Check out this post to learn more about how to plan a road trip.

One last thing. As I live in Portland and we have a van, we have not spent much time in Oregon hotels so I do not have many to recommend.

Permits, Passes and Fees

There are three passes that you might encounter/need depending on your Oregon road trip itinerary. They are as follows:

• Interagency/America the Beautiful Annual Pass – This pass is also known as the “national parks pass” but it offers so much more. It also allows use of many US Forest Service sites, recreation areas, and Bureau of Land Management land. It is currently $80 for 12 months.
• Northwest Forest Pass – This pass is not necessary if you already have the Interagency/America the Beautiful Pass as this pass gets you access to everywhere that the Northwest Forest Pass does. However if you are local and not planning to visit any other federally-managed lands outside of Oregon and Washington, you will save money by purchasing this pass. It is currectly $30 for 12 months.
• Oregon State Parks Pass – For state park areas in Oregon you can purchase an annual pass for $30 or 24 month pass for $50. Here is the link. Daily Oregon State park permits must be purchased on site.

For more information about these passes including fee-free days, check out these links: Oregon State Parks Pass and US Forest Service Pass information.

Leave No Trace

A really important piece of planning your Oregon road trip is protecting the nature that you are visiting. The best way to do this is to learn and follow the 7 principles of Leave No Trace. These are:

• Plan ahead and prepare
• Travel & camp on durable surfaces
• Dispose of waste properly
• Leave what you find
• Minimize campfire impacts
• Respect wildlife
• Be considerate of others

If you want to learn more about these principles or find out ways that you can give back, check out the Leave No Trace website here.

Building the Perfect Oregon Road Trip Itinerary

When planning the perfect Oregon road trip, you should factor in the amount of time that you have, the season that you are visiting in, how much driving you want to do, and how much time you want to spend outdoors vs enjoying the brewery and winery scene. Make sure to check out this post if you are looking for the best time of year to visit Oregon.

Oregon Road Trip Itinerary Day 1 – Columbia Gorge

Let’s get this party started. It’s day 1 of your epic Oregon vacation and you should arrive as early as possible in Portland and rent a car. The first stop of your trip should be a classic – the Columbia River Gorge.

Note: The Columbia River Gorge Waterfall Cooridor on the Oregon side will be implementing a permit system between Memorial Day weekend and Labor Day weekend for vehicles wishing to travel along the stretch of the road between Vista House and Ainsworth State Park (this includes a large majority of the hikes on the Oregon side). For more details, check out this page for information. Please note, you will not need to obtain a permit if arriving via shuttle, private transportation, or bike.

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Some of the best non-hiking spots along the Columbia River Gorge on the Oregon side are:

• Vista House (great for sunset)
• Latourell Falls
• Multnomah Falls
• Wahkeena Falls

Each of these waterfalls has an option to hike if you are looking to do more. Check out this post for the best Columbia River Gorge hikes. If you do decide to hike, this is an area where you could easily spend multiple days. Tunnel Falls is one of the best places to visit in Oregon but it requires an approximately 15 mile long hike to see it which will likely take up most of a day.

@andreafcannon

If you’ve hiked behind a waterfall, where’d you do it? #oregonhikes #oregoncheck #oregontok #hikersoftiktok #hiketokadventure @wandering_jessica_ @andreafcannon @alltrails @Jack Wolfskin @nikwaxna

♬ original sound – Jaxon Roberts

Oregon Road Trip Itinerary Day 2 – Oregon Coast

Day 2 is going to be amazing. You will head to the Oregon Coast. Since you are based in Portland, the best option is to do a small loop from Portland to Cannon Beach to Tillamook and back. If you are willing to move hotels, you could even continue further to the Lincoln City area before turning back east and staying near the winery you plan to visit the next day.

It is important to note that the Oregon Coast is not like a Florida beach. It is likely going to be cold and/or cloudy during your visit. While it might feel weird to rock a rain jacket and boots on your beach trip, you will not be the only one. The Oregon Coast is less busy during the winter and it is also more enjoyable because of the lack of crowds and traffic.

@andreafcannon

Not far from Cannon Beach 🤩 #cannonbeach #pacificnorthwest #oregoncoast #oregon #haystackrock

♬ Adventure of a Lifetime – Coldplay

Here are some of the best spots on the Oregon Coast:

• Ecola Point State Park
• Cannon Beach/Haystack Rock
• Hug Point
• Tillamook Creamery
• God’s Thumb (if you continue further south)
• Drift Creek Falls (if you continue further south)

Oregon Road Trip Itinerary Day 3 – Willamette Valley Wineries

If you are looking for a break from all of the outdoor scenery, doing a winery tour is a perfect plan for day 3. You can book a tour directly from a hotel in Portland where they pick you up so you do not have to worry about getting a designated driver. Or you could move hotels to stay close to the winery(ies) that you are planning to visit. There are so many great wineries to choose from. Here are some of my favorites:

• Solena Estate
• Argyle Winery
• Domaine Serene
• Domaine Roy et Fils

Oregon Road Trip Itinerary Day 4 – Silver Falls State Park

If you are in love with waterfalls then you are going to love Day 4. Silver Falls State Park is home to the Trail of Ten Waterfalls. That’s right. Ten waterfalls in one hike. It is such a beautiful area and not too far from the wineries if you stayed in that area yesterday. The only downside to this trail is that it is not dog friendly. So if you have your pup with you then you should skip this day.

Note: This trail is accessible year-round. However, because it is a waterfall trail it is best in fall-early summer. If you are visiting in the summer when it is not raining and has not rained for some time, this might be a day to skip. However if this is your first time in Oregon, you will likely still find it to be impressive.

If ten waterfalls was not enough, Abiqua Falls is not too far from Silver Falls State Park and it is one of the best waterfalls in Oregon.

Oregon Road Trip Itinerary Day 5 – Mt Hood

If you arrived during the winter, Day 5 should certainly be spent on the ski slopes of Mt Hood. However, even if you are visiting outside of the winter, Timberline at Mt Hood is open 10 months out of the year. Odds are that your trip will fall in one of these months so you can hit the slopes long after you packed your skis away in other states.

If skiing or snowboarding is not your thing, there are still plenty of other opportunities for things to do in the Mt Hood area. However you may want to trade out one of the Mt Hood days for an alternate if you do not plan to ski.

Oregon Road Trip Itinerary Day 6 – Mt Hood

Day 6 of your Oregon road trip itinerary is focused on hiking in the Mt Hood area. There are tons of great hikes in this area so the one that you choose should depend on the season. Four hikes in Mt Hood made the list for best hikes near Portland Oregon. They are:

• Tamanawas Falls – accessible year-round
• Owl Point – late spring through late fall
• Tom, Dick & Harry Peak – late spring through late fall
• Ramona Falls – road not accessible in the winter

If you are looking for something a little easier, check out Top Spur to Bald Mountain. This lollipop trail is only accesible late spring through late fall and is high clearance preferred, although there were many sedans parked at the trailhead.

Oregon Road Trip Itinerary Day 7 – Portland

If you’re taking a red-eye home that gives you time for a sunset in Portland. But even if you don’t, there still might be time to check out the International Rose Garden, the Japanese Garden, go kayaking on the Willamette River, visit the Pittock Mansion, and check out some food carts.

Here are a few of my favorite places to eat:

• My Vice
• The Egg Carton
• Blue Star Donuts
• Burgerville
• The Observatory
• Hawthorne Asylum
• Happy Valley Station Food Carts
• Salt & Straw
• Ox

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Oregon Trip Itinerary

Hopefully this post has given you some ideas for planning an epic Oregon road trip adventure. With more time (and more driving), consider adding Smith Rock State Park, Bend, and Crater Lake onto your trip. Are you planning to visit Oregon? Which spots are you looking forward to visiting? Let me know in the comments.

You May Also Enjoy These Posts:

• Best Waterfalls in Oregon
• Best Waterfall Hikes near Portland
• Best Columbia River Gorge Hikes
• Best Wildflower Hikes in the Columbia River Gorge
• Best Hikes near Portland Oregon
• 10 Places to Visit in Oregon
• Things to do in Bend Oregon in the Spring

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