East Coast Road Trip -- Need Advice

Two friends and I will be leaving from Indianapolis for a road trip this to the east coast. We plan on stopping in Pittsburgh, Philly, New York, and DC before making our way back. We are aware of the touristy things to do in each of these cities, but want to make the experience better by doing some off the wall things between locations or other fun things to make the drive easier. For example, we plan on stopping at Denny's Beer Barrel Pub in PA to take a hamburger challenge. We are also planning a stop in Atlantic City.

Does anyone have any suggestions/advice for what would make this trip better? We are all 22 year old college males looking for a good time. We have contacts in all cities and don't plan on paying for a hotel room the entire time. Any advice on what is going on in these cities from March 7 - 15 would also be appreciated.

Thanks in advance!