The Ultimate Off-Season Oregon Road Trip – Roulette Travel Guide

The Pacific Northwest, specifically Oregon, is a wonderland of lush forests, towering redwoods, megalith and driftwood lined beaches, gushing waterfalls – and much more. But – with the incredible sights, come incredible crowds. Many places in Oregon are as busy as they are beautiful in the busy summertime and shoulder seasons. If you prefer to watch your travel inspiration rather than read it – check out the documentary from the trip below.

I’m a big fan of hitting places in the ‘off-season’ – times of the year that are either colder, wetter or windier than the easygoing traveler would care to deal with. If you’re willing to face one or all of the three – you’ll be rewarded with reduced airfare, lower lodging prices, and perhaps most importantly – little to no crowds. Seriously, there was only one place where we even felt some sort of ‘business’ – but that was midday at Multonmah Falls on a Saturday – even so – we couldn’t complain. However, regardless of when you choose to visit, the guide below will help get you in front of some of nature’s finest offerings in not just the Pacific Northwest, but the entire country.

I’ve broken down the guide into the following sections:

  • Trip Overview and Route –
  • Logistics
  • Costs
  • Daily Recap

Trip Overview and Route

route map from

We began our trip in Portland, Oregon in early January. While I didn’t include each individual stop in the map shown above, you can make your own list or use one of the apps out there to keep track of your wishlist. I prefer as it lets me add my own spots and sometimes help me find hidden gems I wasn’t aware of previously. Here’s the high-level itinerary of our nightly stays and daily adventures:

  • Portland, 3 nights
    • Hikes and Views: Columbia River Gorge, Bridal Veil Falls, Multnomah Falls, Wahkeena Falls, Latourell Falls, Angels Rest Summit, Rowena Crest, Melamoose State Park
  • Keizer, 2 nights
    • Silver Falls State Park, Shellburg Falls
  • Eugene, 1 night
    • New Growth and Old Growth Trail
  • Roseburg, 1 night
    • Tokotee Falls, Umqua National Forest, Upper Table Rock,
  • Grants Pass, 1 night
  • Crescent City (California) 2 nights
    • Jedediah Woods Redwood State Park, Smith River, Samuel Boardman Scenic Corridor, Natural Bridges, Castle Rock, Crescent City Beach
  • Lincoln City, 1 night
  • Portland, 1 night


  • Miles Driven: 1,700
    • Fun Fact: no toll roads in Oregon
    • Fuel Cost: $240 – prices run high as there is always an attendant who pumps your gas
  • Rental Car – Chrysler 300 AWD
    • Pros: awd capability, Apple CarPlay, remote start, heated and ventilated seats (great for drying clothes after rainy hikes), handling and performance, car-based navigation, lots of USB ports
    • Cons: limited ground clearance, so-so gas mileage (24mpg with mostly highways), requires luxury-class or upgrade when booking rental
Rental car pictured on road where AWD was essential.


Overall – I was able to do the trip on quite an affordable budget considering the amount we saw, the distance we traveled, and the quality of our accommodations. Below, I’ve detailed the costs of the trip as accurately as possible.

ItemCost per PersonTotal Cost
Car Rental$228$456
Foodnot a shared cost$330
Flightnot a shared cost$250

The Weather

If you’re willing to trade the crowds and heat for the empty parks of the off-season, be ready for the weather! We saw temperatures as low as in the 20’s (inland and higher elevation areas) to in the 60’s and 70’s along the coast on sunnier days. But – one thing was constant during the trip – the rain. The PNW is already known for its rainy weather, and this is only more so in the winter. And with the rain there can also be snow, sleet hail and everything in between.

I dressed with lightweight thermal base layers, a zip up fleece, waterproof hiking pants, and a waterproof windbreaker when needed. Gloves and hat were also frequently worn, and one of the colder days I also used a balaclava. I definitely recommend having a rain cover for your backpack as well if you’re going to have camera gear as we did.

Daily Recap

Below, you’ll find a recap of the adventure, broken down by day. This will help you get a feel for what is doable during a day, so that you don’t overload your plans – and leave some wiggle room for your own exploration. For most of the locations, searching in Apple or Google Maps for the name as described will give you the general locations, and you can then use AllTrails to find the specific trail you’d like to hike.

Click to the next page to see the day-by-day breakdown of the Ultimate Off-Season Oregon Road Trip!

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