The longest "road trips" I've ever been on were my trips back-and-forth between New Hampshire and North Carolina at the beginning and end of each school year when I was going to college. I'd typically leave at night so that there wouldn't be a whole lot of traffic in the New York/New Jersey portion of the drive, and just drive the entire distance in a single shot only stopping for gas.
I learned to never stop in Joppatowne, Maryland.
I stopped there on my very first trip to get gas and something to eat. While filling my tank I noticed there was a man walking from customer to customer. He was dressed relatively nicely (polo shirt, khakis, and expensive pair of sunglasses), and when he came up to me he gave me this big long speech about how he was taking his family on vacation, but there was some kind of screw up at his bank that was preventing him from using his debit card at the pump, and that he had no cash, and he really could use some help paying for a tank of gas. I pretty much immediately got some strong grifter vibes from the guy, so I lied and told him that I was pretty tight on cash myself and I couldn't afford to help him out.
After getting gas I stopped at a nearby Friendly's restaurant (it was the only thing right off the highway) to grab a quick bite to eat before continuing on my journey. As I was paying the bill for my meal, a woman approached me with another long speech about how she took her son to the restaurant for his birthday, and didn't have enough money to pay for the food, and how she really needed some help or else she'd be stuck washing dishes, and blah blah blah. Because of the odd time of day between meals, I was pretty much the only other person in the restaurant at the time other than a few elderly couples. There were no kids, there was no party. I lied to her too, same lie, then got right the fuck out of Joppatowne.
At the end of the year, this time driving home, I again needed gas and I just happened to be near Joppatowne again. AGAIN at the pump I was approached by another person looking for money for an equally shady-sounding reason. Got right the hell out ASAP.
At the start of my Sophomore year I was joking with my sister about the whole thing, and she noted that it'd be pretty funny if it happened a third time. So on my way back to North Carolina, I made it a point to stop in Joppatowne. This time I went to a completely different gas station. Sure enough though, while I was pumping a man approached me and gave another long-winded excuse for why he needed money for a tank of gas. I looked around and saw that my car was the only one at a pump, so I decided to test the guy. I agreed to help the guy out and asked him how much he needed. He gave me this huge shit-eating grin and told me that $20 should be enough gas to get him to his destination. I smiled back and asked him which pump his car was at. "What?" I repeated my question, and added that I didn't have cash on me and would need to pay for the gas by card. "Oh. Uh... nevermind, thanks anyway..."
So yeah... Joppatowne, Maryland. Grifter central, apparently.