October is definitely Sweater and jacket season around here.

I would recommend maybe looking into checking out a sporting event. Baseball season is pretty much over, but hockey season is starting up soon. The atmosphere at a Capitals game is the best sports options in DC, I think most people who live here would agree. They are very kid friendly as well, my parents took me to caps games when I was your sons age and I’m a fan for life because of it. I would highly suggest looking into one.

Football season is in full swing as well. I’m a bit biased towards the Ravens who are in Baltimore, maybe looking into one of their games. It may take a bit more planning since teams only play once a week; but watching an American football game is definitely one of the big traditions around here.

As far as food, the options you mentioned (Taco Bell, Wendy’s, Panera, etc.) those options are fine if you’re in a more rural or suburban area, but if you’re in DC and you’re going to be in New York, those are two of the richest food cities in the country. As far as kid friendly options, good stuff eatery maybe a good option if you want a burger and fries.

Also, As a native Marylander, trying crab is a must in my opinion. I’m not sure what the best DC option is, if you do make it to Baltimore though, look into Jimmys seafood or Koopers Tavern. Those are my favorite crab cakes in Baltimore.