learning about the east coast

[aloha07]

I'm flying from Hawai'i to Chicago in October -- then to Wilmette and Winnetka, IL, on to Fort Knox, KY, then to Fort Monmouth, Red Bank, and Little Silver, New Jersey. I have a friend in Provincetown to visit, and don't want to miss a beautiful drive -- have a friend in Indiana and could go that route, or stop in Arlington, VA. I really know the West Coast well and Hawai'i and what not to miss there, but the East Coast has pretty much been an arrive in a plane and see the city experience. Thought I could return to Chicago via Niagara Falls...any ideas are welcome on this trip! I'm not used to big freeways, hoping for smaller ones and something lovely.

[AZBuck]

Welcome aboard the RoadTrip America Forums!

First of all, I think these 'family nostalgia' trips can be great fun, a great learning experience, and a great way to reconnect with your own history. I recently made a similar type of trip and had a wonderful time. The one constraint that might really limit you is the amount of time you have for this trip down memory lane. A loop from Chicago through Indiana, Kentucky, Virginia, New Jersey, Massachusetts, New York and back to Chicago, hitting all the places you have mentioned, would require about 2,700 miles of driving. So you'd need about two weeks or more if your intention was to spend at least as much time seeing old haunts and visiting with relatives and friends as you spend behind the wheel. Such a trip would, in fact, take you through some of the best of the northeast. What you now have to decide (or if you've already decided, to let us know) is how much time you have for this, what you were planning on spending (hopefully, enough!) and what your specific interests are. But basically, yes, this is a dream worth pursuing.

AZBuck

[aloha07]

I really appreciate what you have to share, as a friend just said less gently, "You're nuts! And you don't know how to drive in weather!" I have 10 days, so maybe it makes more sense to fly to Chicago to go to Wilmette, Winnetka and Indiana, then fly to New York to go to the rest of the places on my list. Don't know about Fort Knox... that may be a place to possibly drive to from Illinois and Indiana?
I'll check your link out, and again, thanks!
Deb

[Mark Sedenquist]

And you don't know how to drive in weather!"

October is often about the perfect month for roadtripping in the continental USA -- days are cooler and nights are still warm (relative to the deep freeze of February) -- snow is extremely unlikely -- but if you do get into the "white stuff" here are some things to think about. I like Fly and Drive road trips and you might find these tips useful.

Mark

[AZBuck]

There's a way to accomplish most of what you want. If you can leave off Fort Knox and Niagara Falls, then, yes, I think you can have quite a nice trip. Take three or four days in the Chicago area. Hopefully, your destination in Indiana is within range of a day trip from there. Then you have six to seven days for the east coast. A day in Arlington, a half day to drive to New Jersey, a day and a half in New Jersey, a half day to drive to Provincetown, and a day and a half in Provincetown would still leave you a day or two to drive back to the Washington area to catch a flight back to Chicago. I admit it would be very tight, but how often are you going to get to this area? Would such a jam-packed trip be better than not seeing these friends, family and personal historic sites? That's a call only you can make, but you're certainly not nuts for considering it.

As Mark points out, the weather in October will be quite conducive to driving, and the foliage colors in New England will be at peak somewhere. If you've never seen it, that's another reason to make this trip!

AZBuck

[jerseyprincess]

Red Bank is one of my favorite towns in Jersey. Shady tree lined streets, nice shopping district with an very "artsy" feel. Everything is a short walk to the waterfront, which is beautiful anytime of year. (I love the cold weather.)
It shouldn't take you long to explore Jersey, as it's a relatively small state. If I am ambitious enough and get up early, I can cruise a museum in New York City, go to Philly for a cheese steak, stop at my sister's house down the Jersey Shore and make it Atlantic City while the night is still young and not "rushing" at all. (I just debated this with my husband and he agrees this is totally do-able.)

HAVE FUN!