I'm assuming you already tried Google Maps? If I zoom out to show a square box of 50 miles, I see most of the county and town names.

Yes, I use Google maps all the time, but doesn't really have the scale I'm looking for.
You can figure out the distance using the scale given ( one inch=10 miles, or whatever) but you can't really "set" it and then have circle drawn around it.
This is the type of thing I have in mind,
http://www.maps.com/radiusmaps.aspx
but FREE, and with greater details so that the area you want would be a full screen

Hmmmm. What about Google Earth? Not sure if that has it, but it is a very worthwhile download.

Google Earth is good for many things, but no so much for my purposes here.
I really am looking for something that might work with Google Maps, or Mapquest, or some other mapping service that already exits but has this extra functionality.

Maybe we should invent it!

Could buy an atlas and a circle template and do it the old-fashioned way...

I definitely agree that it would be a great addition to the online maps.

Actually, I have done this with a printed map and atlas, and for NYC at least, you can buy 50 mile and 75 radius maps ( I think they're Rand McNally)

I think a website would be really handy when I don't have the forethought to do this manually

Are you looking for a map, or places to visit in certain area?

If for a map, Google Map, click on Print - to get a bigger map in another window, then increase or decrease as you like. Printing is optional.

If for places to visit, "destinations" area on any major travel website like Fodor's or Frommer's. Some of them have samples of travel if you have 1 day, 3 days, 5 days.

Maybe the ostensible reason for this map is the old, "Son/Daughter, I'll put you through college, but not outside this circle."

Ha, ha (gulp).

Hey nstevey--That might be another way to market it! A very practical application...

Dayenu, I'm thinking of several uses that I mentioned in my original post
It would be handy for daytrips, overnight trips, looking for alternative airports, stops along the way for road trips etc.

If I'm doing a road trip,and decide I want to drive another hour or 2 or 5 (50/100/250 miles) I could easily see how far I'd get and where I should look for a place to stay.
Or, if I'm on vacation or a business trip somewhere but I want to get "out of town" one day--say an hour or 2 distance , then it would come in handy.

I know that each of those things can be done with some planning, but I think it would be cool to be able to say
"Here I am--what's within 100 miles that I might not have thought of?"

I hate to beat a dead horse, but I guess the hotels, food or tourist spots that the Google Maps search box returns for a particular zoom isn't good enough, you need more details?

When I'm on a road trip in the US, I use Google maps all the time to find hotels, food and retail stores. It works pretty well for me.

Not sure if it is really free but it came with my computer, Microsoft Streets & Trips allows me to find nearby places and then I enter the number of miles and it draws a circle on the map and then lists all of the different categories (airports, trains, restaurants, etc.) for more information.

This works pretty good: zip-codes.com/zip-code-radius-finder.asp?

If your looking for a wider radius at once, there was another good site, but I forgot it. The site was a home buyer site, so it might have been something like: homebuyer.com type of site, but not that one, it gave you the option to list all towns within a certain radius.