My best friend Julie and I took a road trip through time on Route 66 (in Arizona it's called I-40 now).
Route 66 is perhaps the single greatest road trip for baby boomers. At a time when the cross-country interstate was in its heyday, families in the 50s and 60s were road tripping in their big cars with kids on board, staying at motels with quaint swimming pools and quarter machines for vibrating beds.
Our trek took us through Flagstaff, Arizona east to Holbrook and down the Mogollon Rim. And what an amazing trek just for that one portion! We plan to do the western portion from Flagstaff to Lake Havasu next springtime.
Although much of this has become derelict and abandoned, the nostalgic content is a potent one -
Road trips - the family standard of our upbringing. Consider updating this practice with a cooler of bottled iced teas, some ranch dressing/buffalo sauce/turkey/shredded celery and carrot in a roll up tortilla, some brownies. Instead of packing the kids in the back, find some friends who want to brave the open road and go back in time. Be sure to book motels that have that vintage mid-century feel. Stop at every cheesy gift shop. This is your trip - your way!
Here's a great resource for planning -
Route 66 planner