We are a family of four (2 adults, 2 kids 5 and 8). Wanted to get thoughts on our itinerary and suggestions for Family Friendly Activities in each destination.

Portland (4 nights, vrbo) - suggestions of must do activities? Restaurants?

Cannon Beach (3 nights, rented a lodge)- want to do ecola State Park for sure and Haystack. What else? favorite ice cream shops and places to eat?

Portland (1 night, hotel)

Heading Toward Bend but don’t have a plan until we need to get to a motel just north of Crater Lake two nights later. Any ideas? Where should we stay?

Motel just North of Crater Lake (1 night)
What should we actually do at Crater Lake other than drive around the Rim? Do we need to book in advance? Should we book a dinner in the dining room at the Lodge?

Leave Crater Lake and Drive to Medford. Fly home 5 am from medford the next morning.

Thanks all!

We had a great breakfast at Lazy Susan Cafe in Cannon Beach. The Harding Trading Company had excellent coffee.

We rather enjoyed our day trip to Astoria from our Cannon Beach base.

Loved, loved, loved Bend. Our kind of place.

Yes the LazySusan is probably the best breakfast place in Cannon Beach. CB has been a family favorite of mine since I was a child. Definitely go yoPublic Coast Brewery. Not just for the beer, which is excellent, but also very good good. Pelican Pub is good too. Wayfarer is good but a bit nicer. Bruce’s Candy shop is not to be missed.

Bend has so much to offer. We always stay just south of there a few minutes at Sunriver Resort. Such a great place especially with kids!

At Crater Lake be sure to do the boat tour! If there are spots, getboff at Wizard Island to hike and they will come back for you later.

When will this take place?

Thanks everyone! Early August

many of the Crater Lake options are booked already!

A few places to check in Crater Lake area- not necessarily north of CL.
There is Steamboat Inn, Diamond Lake Resort, Dogwood Motel on HWY 138 and Prospect Inn in the tiny town of Prospect. Steamboat Inn would be the most plush of the suggestions, The Dogwood is a pretty basic motel, Diamond Lake is rustic but has lots of things for kids to do, the Prospect is an old stagecoach inn, not much to do there but decent place to stay and great meals.

Hwy 138 has a lot of wonderful waterfall hikes- some are very short walks, others longer. Watson Falls and Susan Falls are a couple of favorites. Bring insect repellent.

In Portland, The Spaghetti Factory is kid friendly but also nice for the adults. Then take the Aerial Tram up to the observation deck of the hospital Great view of the city. The zoo is also very nice. All are accessible with public transportation.

We stayed at the Embassy Suites on 3rd and Pine. Very nice and accessible to anywhere.

Given the distance, the heat (could easily be in the 100s), the lack of accommodations and the (probably) very high one-way car rental surcharge or drop fee, if it was me I'd just shelve the Bend/Crater Lake part for now and do it on a future trip, perhaps one where you could include the southern Oregon coast (IMO the nicest part) and the California redwoods.

Instead, if it was me - and it's certainly NOT - I'd extend my time on the coast, visiting Cape Disappointment across the mouth of the Columbia, and possibly head as far south as Yachats ("ya-hots".) I'd use the remaining days around the Hood River Valley and Mount Hood. There are tons of family-friendly things to do around there; google these places: Lost Lake, Maryhill Museum, Hood River fruit loop, Bonneville hatchery and Herman the Sturgeon, Flying L Ranch, Timberline Lodge... just for starts.

That way you could return the car to Portland and (probably) save a ton of money by not paying for a one-way rental.

Yachats is lovely. I agree with more time on the coast. While lots of people love Bend it's gonna be HOT in August!

We got a pretty decent price on the car and booked miles tickets out of Medford. So, can't really change the itinerary now but really appreciate your comments.

I would take mms advice and stay at Sunriver if you can find a place. So much to do there for kids and adults they might not want to leave.
There are many ways to make reservations at SR as most places are privately owned - there are property management companies, Flipkey, VRBO etc etc

Agree on Sunriver. But I think your priority is Crater Lake reservation first.

Call all the places Sunbum suggested for Crater Lake for a reservation, plus the lodge for cancellations. Don't just look online, some of these places are little and their websites may not be updated. Call. When you're calling, ask if they have one night earlier available instead. I have an idea for you on that. below.

Once you have a reservation for near Crater Lake... here's what to do next: For Crater Lake itself, if your kids are up for a hike down to the water from the rim, you can do the boat ride. This should be reserved ahead. It was so much fun for my family. One of our favorite days. Getting off on the island and then getting back on the next boat was a highlight. Their dad jumping into the cold, cold lake was another.

Spend that night in Medford or near it.

The day before you fly out, visit Ashland in the morning. Try on costumes at the museum, visit Lithia Park and the shops. Then go up to Grants Pass on the Rogue River for an afternoon jetboat ride (which you will also need to reserve). These are so much fun, and even more so when it's hot out. Wear swimsuits. It was 106 degrees when we did it and the animals were all down by the water even though it was middle of the day.

Another night in Medford and then home.

Thank you all for the suggestion