my dad's insistence on stopping at Fort Frederick in Maryland every time we went to visit my aunt who lived outside of DC.

As an adult, I really haven't taken many vacations outside of visiting relatives. So the vacations themselves have been good but the travel there and/or back was not always the best. In that regard, I'd say the time I drove to my parents' house in Erie, PA for Christmas and due to snow, I-90 was closed from Buffalo to the PA state line so I had to drive that stretch on Route 20, going about 20 miles per hour the whole time. An hour and a half drive ended up taking 4 hours. I could have stayed at a hotel right off of I-90 but I wasn't feeling tired yet so figured I'd try to drive a little bit further...get a little closer before stopping. Bad choice there as there were no places to stop once I got outside of the Buffalo area so I just kept driving.

"Dressed up like an evil villain dressed up like a soccer dad"