You have a great route picked out! There is so much to do in the outdoors in Oregon from Eugene through the southern part of the state. You’re going to love it. Here’s what not to miss:
If you go from Eugene to the coast, make your first stop Reedsport, to check out the amazing Oregon Dunes. This post will tell you a lot more about it. We like to camp nearby and play on the dunes, but it can be done as a day stop, too. Next, stop at Sunset Bay State Park (near Coos Bay), and hike the coast trail that goes from the park to Shore Acres (there are beautiful gardens there, and along the way, great cliff sea views). As you make your way down the coast, the towns of Bandon and Gold Beach are worth poking into as well.
At Brookings, take the time to explore the redwoods, detouring east up the Chetco River to see beautiful Alfred Loeb State Park and, just a bit farther, the Redwood Nature Trail. Then head toward Grants Pass on the Redwood Highway (199), stopping at additional redwood groves. I recommend the Simpson Reed Grove Trail, right off the highway, for a short hike, or the Boy Scout Trail (off 199 on Elk Valley Road) for a longer hike.
Continue on 199 toward Grants Pass, but stop in the little town of Cave Junction to check out Oregon Caves National Monument (the tour is about 1.5 hours, and it will take you about 30 minutes to get there from Cave Junction). There’s also an excellent natural grocery store in town that has a deli counter serving many vegan foods. It’s called Diggin Livin Natural Foods.
In Grants Pass, head south on I-5 toward Ashland. Now you’re in wine country, and you’ll want to make some stops (or backtrack from accommodations in Ashland). Try the Applegate Wine Trail and/or the Upper Rogue Wine Trail (info here). Some of my favorites are Kriselle (great views of Table Rock), Red Lily (creek front in Applegate Valley), Dancin’ (beautiful site in Jacksonville), and 2 Hawk (in Medford). You can’t go wrong! All southern Oregon wineries are casual and friendly and bottling great wine!
In Ashland, you have a number of excellent restaurants to choose from, most of which serve some vegan foods. You should also check out the Ashland Co-op, which has a wonderful deli counter with vegan offerings. We also love Sesame, Amuse, Mix, Flip (great mushroom burgers), and Sauce (rice bowls).
Enjoy your time!