Need Ideas

You could fly down to HSV, we have the US Space and Rocket Center here. Get enough time and you could hit BNA and CHA at the same time. You can't camp at HSV but look up Moontown close by and you should be able to camp there.
 
If you're a fan of AOPA and/or aircraft museums, I'd suggest Northern Virginia. AOPA is headquartered at FDK, they'll give you a free tour of the place and introduce you to the president of AOPA. The Udvar-Hazy Museum is located at IAD (Dulles). http://www.nasm.si.edu/udvarhazy/ If you're not in the mood to land at a Class B airport, land a few miles away at Leesburg, Va(JYO). Both JYO and IAD are within the SFRA, but the FAA online course will give you all the info you need to navigate it properly. Also, you can drop me a line. I instruct at JYO, and I'm good for a ride to the museum.
 
So, I have this 100 hr block of time that I'm flying in a Cessna 150. I've flown about 25 hours of the 100 now and there is really nowhere that sounds appealing to fly to around here now. Does anyone have recommendations on fun airports/stuff to do near the airport within the circle on the map? The closer to TOL, the better because it's hard for me to get time off of work right now. The most time off I have is two days back to back. The edge of the circle is about 5.5 hours flying time, so I'd probably have to spend the night if I wanted to do anything.
I've been to ORD (not at peak) and MDW, both really easy. Going into IND I was vectored like 30 NE for the ILS but BHM and BNA are easy ones.
Panama City, before it closes!
Great bars on the beach too!
 
As in the 3 in the FRZ? College park, Potomac and Hyde. I believe they allow transient traffic now, however you have to apply for a PIN and pay for a background check through one of the FSDOs down that way, and I believe sit in on a class. Its probably not an option for someone thats only going down there once, although I could be wrong.

There is the Udvar-Hazy museum at IAD.
You can walk to the Rock and Roll Hall from BKL.
Fly over Niagara falls maybe
BKL and IAG are great!
 
Head east over NY, overfly Niagra Falls, then head to NYC to fly the corridor. I'm not sure when Old Rhinebeck starts their airshows (WWI reenactments) somewhere northwest of NYC. There's a resort/airport somewhere in NJ I think it's Flying W you could stay at, then come back west.
Maybe check out adventurepilot.com for ideas as well.
 
Thanks for all of the great info. I'm gonna try the Waco Museum, IAD for the Smithsonian, MDW/ORD for pizza and Mackinaw.
 
The restaurant at FTY (Fulton County northwest of Atlanta) has fried green tomatos on tuesdays.
 
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