Wife and I are racing 70.3 CDA this summer and turning it into a week long road trip with a few other stops. Looking for advice on anything cool to do, breweries, restaurants, or bike/run routes (bear in mind we will be in taper and recovery)

Day 1: Drive from East Bay to Bend. Looks to be 8 hr drive. We are staying at the Tudor Inn, so figure we arrive early evening. Probably looking for a light shakeout run and then hit a brewery and dinner
Day 2: Drive from Bend to CDA. Looks to be 7 hrs, but not in a rush. Might be nice to spin for 90 minutes and have breakfast in Bend, then plan to arrive in CDA closer to 6-7pm
Day 3 - Day 5: In CDA for race which is on Day 5. Thoughts on things to do away from the race in CDA?
Day 6: Drive from CDA to Walla Walla. Only 3.5 hour drive, but the goal is to hit wineries in Walla Walla, any recs on wine or food? Maybe a trail for a light shakeout run?
Day 7: Drive from Walla Walla to Crater Lake: 6.5 hour drive, so will want to get an early start to maximize time in the park. Planning to ride the perimeter, just not sure if we would do it in the evening or next am
Day 8: Drive from Crater Lake to East Bay. Another 6.5 hour drive, but we want to spend a few hours in the park in the am. Again, not sure if am is best time for a perimeter bike ride, or previous evening.

Thanks for any feedback