Oregon- Help or Advice
 

My wife is attending a 3-day conference in Portland and we have decided to make a family vacation out of it. The two of us plus our 15 yr old son arrive very late on Sat. July 23rd. Her conference is July 26,27,28 and we depart Portland on Sun. July 31st at 150pm.
The issue is that we would like to see a number of sights, but for 3 days my son and I can only take day trips out of Portland (interested more in nature than city). In the evening, my wife could go with us if it's not too far from Portland.

I would like to squeeze in:
a portion of the Columbia River Gorge and Multnomah Falls
some short hikes (5 miles or so)
Mt St Helens in WA
a section of "classic" OR coast
Crater Lake Ntl Park

Any help would be appreciated!!! THANKS!

Will you be flying into PDX and renting a car?
Depending on where the conference is in Portland, you might want to ride the light rail into the city and rent a car from downtown when you need it. The TriMet light rail Red line is right outside baggage claim at PDX. If you rent at the airport, head east on I-84 and then get on the old Columbia Gorge highway (old US 30) to get to Multnomah Falls.
There is a good paved trail with steps up to the top of Multnomah Falls. East of M. Falls there are other falls with trailheads off the old highway. There is one that I remember that the trail goes in behind the waterfall.
I would choose a day going around Mt. Hood instead of the long drive out to see Mt. St. Helens with the long drive back to I-5.
For your trip over to the coast, take US 26 west to US 101 and drive north to Astoria to see the Astoria Column and the docks.
Drive 101 south to Cannon Beach and Haystack Rock. Drive to the Tillamook cheese factory for the self guided tour and get some free samples before buying some cheese and/or ice cream. See Cape Meares and then head back to Portland on Rt. 6 from Tillamook connecting back to US 26 west of the city.
I'm thinking that Crater Lake is a bit too far for a 2.5 day trip from Portland.
The Evergreen Aviation Museum has been having some financial trouble. I hope that they are still open this summer so you could go and see the "Spruce Goose" and the rest of their collection near McMinnville.

With so little time, I would not waste any on the cheese factory. Tillamook cheese is available in many parts of the country.

If you are going to drive as far as Astoria and then south you might at least consider the short detour over to Cape Disappointment in Washington. The lighthouse and setting are certainly iconic and have appeared on so many calendars over the years we felt we simply had to see it on our drive from Seattle top Cannon Beach.

I am NOT saying it is a so-called "must" but you might want to check out that possibility before making any final route decisions.

Haystack Rock is, AFAIK, about as "Oregon Coast Symbolic" or at least one symbol as it gets. There are other haystack rocks but if you are going to see one of them, this may be "the" one.

I'm confused. Are you considering Crater Lake as a day trip or are you thinking of going there after your wife's conference ends? It's too long of a trip for a day trip and, honestly, I'm not sure I'd travel that distance for the remaining time you between her conference ending and your flight home either. I think the coast is a better option for those days.

In the time you have, I would focus on the Columbia River Gorge and the Oregon Coast.

Investigate the gorge as far as Maryhill, WA, including the stretch of WA-14 from Maryhill to Bingen.

Travel the coast from Cannon Beach to Florence, including Ecola State Park just north of Cannon Beach and Cape Perpetua.

Book rooms well ahead. You will be in these areas on busy holiday weekends.

Crater Lake is not a reasonable destination in the time you have.

As unlikely as it may seem, it takes longer to drive from Portland to the visitor center at Mt. Saint Helens than it does to drive to Paradise at Mt. Rainier, and Mt. Rainier is a much more impressive destination.

HTtY

For the 2.5 days after the conference, I would do the coast trip or the trip out to Mt. St. Helens or maybe Mr. Rainier.
Whether you stop at the cheese factory or not, be sure to go at least as far south as Cape Meares. You might have time to go as far south as the Oregon Coast Aquarium south of Newport.
I know you can get Tillamook cheese in many states. You can get wine in most grocery stores so why would you "waste your time" going to a winery?
The cheese factory is the only place I ever bought Tillamook cheese curds.
Their ice cream is great and it is not widely available.
The Haystack Rock at Cannon Beach I am told is the most photographed spot in Oregon.
Oregon has a beautiful state capitol building in Salem.

You have two full + days on each end of the conference. Your wife will not want to miss the coast or the gorge, so try to do those on the days she has free. Then on the conference days, I would stick closer to Portland.

For the coast, summer is high season and the hotels book far in advance and around Seaside and Cannon Beach, most places require 2-3 night minimums, so I would get that portion booked asap. You could do a nice loop heading west on 26 from Portland and head over to Cannon Beach. That takes about 90 minutes on a typical day. Two must do's there are Ecola State Park on the north end of town, and then Haystack Rock. If you decide to do this and need hotel suggestions, just ask. We head over there often and have for many years. Then head down 101 and take highway 6 back towards Portland. It will connect with 26. Highway 6 goes along the Wilson River and is quite scenic.

For the gorge, you could do it while based in Portland, but I would opt for at least one overnight there. Head east on I-84 and get off at either exit 17 or 22 and get onto the old scenic highway. It parallels 84, but this is the road that has all the scenic stops. Must stops include Portland Woman's Forum (odd name, great views), Crown Point Vista House, and Multnomah Falls. MF gets very busy, so I would head out of Portland early to get a jump on the day. There is a one mile trail to the top of MF, and it is paved for a bit of it, but not all the way. It is fine, but not near as exciting as most of the other trails in the area. There is a platform at the top to look over the falls, but it sounds more exciting than it is.

Then keep going, stopping as you like, until Hood River. Fantastic town with breweries and good food. After this you can take a detour to highway 35 to 26 and go to Timberline Lodge on Mt Hood, or do this on a day without your wife if she doesn't mind.

I would continue back on I-84 then past The Dalles to Biggs Junction and cross the bridge there. Stop at the Stonehenge replica, then head back west on highway 14 which follows the river back to Portland. Stop at Maryhill Museum, Horsethief Butte which is a rock climbers paradise and is just really cool with great views, and then maybe stop at Columbia Hills State Park to see the petroglyphs. You can cross back over to the WA side at a few spots along the way.

As for hiking, we do a lot of that in the gorge but there are so many great ones that I hate to make recommendations without knowing what you like for elevation.

Mt St Helens is wonderful! That would make a good day trip if your wife doesn't mind missing it. It is only an hour from Portland to the exit 49 off I-5 north. From there, you get onto the road up to the mountain, which is 50 miles and is a slow road. Stop at all the visitors centers along the way as each has a difference focus. That said, definitely allow time for the best, which is at the end of the road, Johnston Ridge Observatory. There is a short film there that is a must! You can also do some hiking from there. Go to the far end of the parking lot and you will see a trailhead.

Another good day trip from Portland is to head south towards Salem to Silver Falls State Park. There is a nice trail there called the Trail of 10 falls, anti is about 7 miles long. Not difficult at all. The first falls are huge, and you walk under and around them. If it is a hot day, you can go down to the bottom and cool off in the water.

Unfortunately you really need more time for Crater Lake. From Portland you are looking at about 6 hours each way just to get there. It is great, but I would keep that for another trip unless you can add a day or so to your trip.

THANKS for all the great information.
To answer a couple of questions: yes, we are flying in and out of PDX and we will have a car rental for the entire time.

My son and I could do a day trip to Mt. St. Helens without my wife, because that's something that is a "must see" just for the two of us. I think we'll do the Silver Falls Trail and Mt Hood while she's at the conference. I must get to the Timberline Lodge just to check it out.

I was really hoping to get to see Crater Lake and was willing to do the 5-6 hr drive to get there. But it would require an an overnight and I see how I would need to give up the Coast or the Columbia River Gorge. I can change my Southwest flights to Monday for no fee to add one more night if Crater Lake is worth the effort. Her conference ends at noon on Thursday so we have part of Thursday, all of Friday and Sat and have to be at the airport by 11 am or so on Sunday.

Is Crater Lake worth the extra effort? I don't think we will get back there if we don't do it now.

Silver Falls hike is one of my favorites. If you park at the South Falls, there is a visitors center where you can get a trail map. There is also a concession stand where you can get snacks before or after the hike.

Crater Lake- it is beautiful but it's a long drive unless you plan to do some other things
Hwy 138 between Roseburg and the lake has numerous hikes- some just a short walk from parking lot, some longer. My favorite is Watson Falls and Susan Falls.

With a 15 year old son, you might enjoy the Bend area more, lots of hiking, biking, rafting. Maybe a gondola ride to the top of Mt Bachelor.

Sun River is a great resort to stay at. Bike rentals, lots of trails, horseback riding, kayak rentals- short drive into Bend.

If you can add a day, then do:) I definitely think Crater Lake is worth it! You could leave Thursday when she is done and be down at Sunriver by 4ish. Sunbum mentioned Sunriver, and that is where we always stay. Fantastic place! Crater Lake is only 90 minutes from there. Go early on Friday and do the boat tour. That is a must IMO! I think you can buy tickets online now, but we have always just shown up very early and bought them the day of, but if you can do online I would do that to secure spots. The hike from Cleetwood Cove down to the boat docks is about a mile and 700 ft elevation loss. We have done it with little kids and older family and everyone was happy they did. Sometimes people get winded on the way back up, but there are benches if you need.

You can also drive all the way around the rim, or take the trolley ride.

You can do all that in one day.

I would then do the gorge on your way back up to Portland, taking 97 to 26 to 35 to 84.