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Here We go Again on an Oregon Road Trip

Planing an Oregon road trip

Will our car get this dirty on an Oregon road trip?

By May, are your boomer travel feet itching for a road trip? Ours are! Alan’s had the maps out designing a late spring Oregon road trip that will take us from Crater Lake National Park to off-the-beaten-path destinations in eastern Oregon. And he’s arranged outstanding accommodations along the way. I love a man who’s a travel planner.

Our Oregon Road Trip Itinerary

Day One:

The trip begins from Missoula, Montana, as we make our way to Pendleton, Oregon, for a one-night stop.

Days Two, Three and Four:

On the second day, we arrive at Crater Lake National Park to spend three nights at Crater Lake Lodge. Since this is a last-minute trip, you may be wondering how we were lucky enough to snag three nights at a popular national park lodge. Think snow, as in crews are still clearing the famous rim drive which doesn’t open until July. Since most hiking trails will also be snow-covered, we’re bringing snowshoes. What could be better than snowshoeing in mild, spring weather?

Days Five and Six:

After leaving Crater Lake National Park, our Oregon road trip connects with Journey Through Time Scenic Byway (an Oregon State Scenic Byway). Although we won’t be driving the entire 286 miles, highlights include John Day Fossil Beds, a side trip to Painted hills and Thomas Condon Paleontology Institute. Riverside School House Bed & Breakfast in Prairie City is headquarters for this portion of the trip.

Days Seven, Eight and Nine:

What will the Memorial Day celebrations be like in Joseph, Oregon? We’ll let you know as Alan and I spend three days exploring this mountainous corner of northeastern Oregon. Most of the Hells Canyon Scenic Byway won’t be cleared of snow, yet. But we’ll explore the portions that are clear as well as hiking or even snowshoeing. Pedaling the rails with the Joesph Branch Railriders is also on the to do list. Following our philosophy of building relaxation into a trip, the Bronze Antler Bed & Breakfast will be the perfect place to kick back for an afternoon of doing absolutely nothing.

Day Ten:

Drive to our Montana headquarters in time to complete the final plans for the next road trip: a June ride on the Beartooth Highway!

Alan has purposely left the itinerary loose. Who knows what boomer adventures, scenic byways and food finds I’ll be writing about for the readers of My Itchy Travel Feet? In the meantime, as Internet and time allow, I’ll be sharing photos, videos and short reports at the My Itchy Travel Feet page on Facebook and Instagram. Hope you’ll follow along. I’m determined to master the art of Instagram stories and Facebook live reports (you’ll need to follow my profile for the FB Live videos).

A special thanks to Tim Bishop of Baker County Tourism who offered excellent advice on putting this trip together. And this is a boomer travel reminder on how valuable local and state tourism organizations can be for planning travel. Don’t forget to check them out when organizing your trip.

Do you have a favorite Oregon road trip? Come join the conversation at the My Itchy Travel Feet page on Facebook. Or send us an email with your thoughts.

Disclosure: Affiliate links are included for your convenience. However My Itchy Travel Feet receives a small percentage of the sale at no additional cost to you.

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