As I’m planning my Oregon road trip, I feel like I’m planning three separate vacations. First, I have four nights to spend along the coast. Then I have four nights in Ashland for the Oregon Shakespeare Festival. Finally, I have six or seven nights to meander back north through central Oregon.

This map shows my current thinking of how I want to spend my time.
B: Cannon Beach (2 nights)
C: Myrtle Point (2 nights)
D: Ashland (4 nights)
E: Bend (3 nights)
F: Fossil (3 nights)

Each of these mini-vacations requires separate planning. Since Ashland required buying theatre tickets, I did that first. The dates and details are all settled. I’m arriving on Wednesday, September 25, and staying four nights at an apartment in the heart of Ashland.

My friend Mary is going to come down to Ashland and we’re going to see five performances over four days.

  • Cymbeline (Wednesday evening)
  • My Fair Lady (Thursday afternoon)
  • The Heart of Robin Hood (Thursday evening)
  • A Midsummer Night’s Dream (Friday evening)
  • The Unfortunates (Saturday evening)

That gives us Thursday morning as well as most of the day Friday and Saturday for leisure time in Ashland.

For the coastal part of my trip, I have four nights. I’m looking at spending the first two nights around Cannon Beach or Seaside. Then I’ll head south along Highway 101. And I’ve booked two nights at a farm in Myrtle Point.

The third itinerary is the one I’m struggling with the most. My original plan was to head to Crater Lake, maybe stay in that area for a night or two, then Bend for three or four nights, then maybe a night in Portland before heading home. But I’ve gotten some advice from a number of different sources that are making me think of dividing the time up differently over the second week of my trip.

I posted a query on Thorn Tree Forum, and those who’ve responded are urging me to make Crater Lake a quick stop, skip or at least cut back on my time in Bend, and head to Fossil for a few nights at Wilson Ranches Retreat, and then to Timberline.

I’m still thinking this all through, and I’ll post more about these different options and what I decide once I do decide.

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