After 3 years of planning, I am riding Route 66 starting June 8

[tntnj]

+1 on weather for temperature in the deserts. We left Flagstaff, AZ, in late June: it was lower 50's. By the time we reached the Colorado River, crossing on I40 down the mountain from Kingman, AZ, that day, it was 110°F! At 200-300 miles a day, you should be able to avoid mid-day riding.

Have an enjoyable and memorable adventure!

I am aw

NJ to the head of Rt66 in Chicago is ~12-14 hours (800 mi) of saddle time.
It is doable in 1 day but your pace looks like you may need to plan a 2nd day to Chitown.
BTW, I have that route all mapped in GPX segments if interested. You can drop in your POIs along the way.

I am thinking of driving to South Bend -Gary IN for the first stop Then to Chicago the second day.
I think you sent me those but I could not get base camp to load and view on the Garmin GPS

 

[racoon]

I think you sent me those but I could not get base camp to load and view on the Garmin GPS

I still have Basecamp installed on my computer but gave up on it.
I asked Google how to import a GPX file into a Garmin 396 and it said:

• Computer (Recommended):
  1. Connect the Garmin 396 to your computer via USB cable.
  2. Open the device drive (labeled Garmin or zumo).
  3. Copy and paste your .gpx file into the Garmin/GPX folder.
  4. Disconnect safely and restart the GPS.
  5. On the GPS, go to Apps > Trip Planner > Menu (three lines) > Import to make the route active.

There was also a section on using Basecamp and one on using the Garmin Explore App on a smart phone.

 

[RayBJ]

I plug my 595 into my PC, run Basecamp, and once the PC 'sees' the 595, I drag & drop my routes directly to the 595 'user data' folder that (should be) listed on the left border library. I don't know what the 396 connect capabilities are. Basecamp is at end of life but I still use it a lot.
If the 396 has a removable SD card, you can copy the files to the /garmin/gpx/ folder on the SD card.