I enjoy reading your posts - esp. about how short the weekend is.
I market "Day Stretchers" tm - for people with everything except enough time.
I suspect you will find the empty blocks of time and space on your trip delicious.
I don't listen to music or fixate on my gps maps or keep the gears in my head spinning.
I just pedal and look at things around me.
If you are flying into Portland without vehicle support at first - the Westport will be hard to get to.
The easiest places to reach on the coast are either Astoria or Tillamook.
How do you plan to get out to the coast - do you have a friend who might ferry you?
Otherwise there are morning & evening buses to both from downtown.
Also, I find it easier to ship my bike to a bike shop right on the coast -
Rather than schlep it through airports, trains, buses & taxis.
Sometimes it is cheaper to ship than to pay the airline bike fee, too.
Astoria would probably be the easiest to get to - plus they have a great bike shop.
Link to bus connection - http://oregon-point.com/northwest-point/
There's a scenic old shipwreck at Fort Stevens State Park.
What that means is that the initial ride will be busier and hillier than the Westport route.
Even though you may be following the Columbia River - there are high bluffs to cross.
I would suggest the first 30 miles on the Oregon side on US 30 -
Then take the Cathlamet Ferry to Wash and do 30 scenic miles on WA 4 to Longview.
There's camping in Cathlamet - plus an old historic hotel. It's a charming old river town.
Would you be camping or moteling it the first two weeks before your husband arrives?
Cathlamet would make a short 1st day with time for a slow start and not overdoing it.
2nd night could be up near Toledo and then onto US 12.
If you really want to stick with Westport as a starting point - it will take some work.
Snow by mid-June in western Wash/Oregon - nope.
Although there might be some still on the ground at higher elevations.
Care must be used with RidewithGPS and other Google maps.
Google is not necessarily our friend. Esp. in the West - if you pick the bicycle option -
it will send you on all kinds of dirt, private, closed, even nonexistent roads.
If there are no bike trails, sometimes it is better to use the auto option.
Have a nice week.
Pic - Cathlamet Waterfront (Not French like Cath-lam-MAY, but Chinook Cath-LAMM-it)