September 14th we are leaving Crescent City, after visiting the Redwood Forest area. On September 17th we fly out of Portland airport. Around 1pm flight. We are looking for things to do on way to Portland. One thing for sure is visit a winery and stay in area. I see many Wine areas on the Map. Can I get some recommendations on city's, wine areas and other ideas on places we need to see on way back?

You will get off US 199 near Grants Pass. Head south on I-5 toward Medford. Between Medford and Ashland, visit Roxy Ann
http://www.yelp.com/biz/roxyann-winery-medford
You might be lucky enough to see a play in Ashland.
See Crater Lake on the way to Bend for 1 night.
Enter Crater Lake NP using the south entrance off Rt. 61 and exit by the north entrance onto Rt. 138. Bend is 90 miles or 1:45 from the north entrance.

Highway 101 up the Oregon Coast is a very scenic drive, and there are many wineries in the Willamette Valley near Portland.

HTtY

Yes, we have over 400 wineries in the Willamette Valley AVA alone Pinot Noir is what this region is known for, but you will find other varietals as well. Take a look at the McMinnville to Newberg stretch as that is where the bulk of the wineries are.

Thanks, we are driving the Oregon coast on way to Redwoods so would have seen that.

A few weeks ago we drove from Astoria to Florence and back again. It was beautiful both ways--a much better option than I-5.

HTtY

We are thinking of skipping Crater Lake. We definitely want to see the wine fields. We love trails and outdoors so if there are any stops we should make, please mention them.

Even if you skip Crater Lake NP, try to come through Bend and then head for The Dalles and the Columbia Gorge wineries.
http://www.columbiagorgewine.com/wineriesvineyards.html
There are a few good trails at the great waterfalls on the Oregon side of the Gorge.
Multnomah Falls (Oregon's tallest) has a great paved path and steps up to the top. The view is great from up there.
Skipping Crater Lake would mean taking I-5 north to Roseburg and then Rt. 138 east up the Umpqua River which has some great hikes as well.