As someone mentioned earlier, Pittsburgh is great - more 'overlooked' perhaps than small, though, especially by non-Americans. I'm British and hadn't really considered it before I had the opportunity to go.

I went last year to see Bruce Springsteen and spent a couple of days, it's a great place to walk round, and it's in such a lovely setting with the rivers on two sides and all those bridges make for some great photo ops, as does the view from the top of the inclines.

Pt II
 

Let me add a few more votes for some that were already mentioned;

Hilton Head, SC: (stay at the Marina)
Naples, FL: great food and beaches
Boise, ID: skiing, golf, good food
Eugene, OR: wine and food haven
Bellingham, WA: (check out Fairhaven and consider taking the Alaska Ferry north)
Bishop, CA: the majestic Sierras...
Vancouver, BC: big, but should be on everyone's list
Park City, UT interesting old mining town, touristy but better than some IMO
Walla Walla WA, wine, wine wine...gonna be the next Napa in another 15 years or so

And add this for you who want to ski in the AM and play golf in the PM:
Wenatchee, WA it's hard to get to but a ski bum town in the making.

also:
Kelowna, BC:skiing, golf, BC wine country
Cannon Beach, OR (the NW version of a CA beach town)
Telluride, CO winter skiing but summer is cheaper and you can get into some serious hiking....

Naples, FL is pretty boring for me...

Juneau, AK and its environs are pretty freakin' awesome. It's what the Alaskans call a "big" city, but it's pretty small population wise...The city limits covers quite a bit of the wilderness though.

Any big university town @ homecoming weekend...priceless.

I was planning for MS but I guess I am going to miss all this. :(

I spend a heap of time in Spokane - where one of my biggest clients is headquartered. I really don't care all that much for MOST of the city, though downtown has, indeed, come back to life. Auntie's Bookstore is great. The Davenport Hotel. The river area (aside from the dead of winter, which really is both "dead" and "winter".) Some good restaurants too. The bus system is great.

I live in a big, cosmopolitan city(Chicago) and these are the smaller towns that keep my partner and I going back over and over:

Louisville
Austin
Asheville
Aspen
Savannah
Santa Barbara
New Orleans
Thomasville,GA
Paducah, KY

Tahoe is another good one for ski AM golf PM, although typically we've driven down into the desert (maybe 45 min away) for the golf.

Excellent March Madness destination...usually great snow up on the mountain and warm temps down in the desert.

How about medium to tiny?

Charleston, SC (with a sidetrip to Bull Island)
Beaufort, SC (with a side trip to Hunting Island)
Asheville, NC
St, Augustine, FL
Fredricksburg, TX (with a side trip to Enchanted Rock)
Bisbee, AZ

Probably all repeats here:

Austin, TX
Colorado Springs, CO
New Orleans, LA
Huntsville, AL
Chattanooga, TN,
Knoxville, TN
Savannah, GA
Asheville, NC
Portland, ME

I like living in medium sized cities too; 50-150K populations seems about right.

More than corn...
 

Longtime flyertalk lurker, but what a better reason to post than to talk up my city.

I could give you a thousand reasons why Indianapolis is one of the best small-big cities in the country. It's always overlooked or pegged as a racing/basketball town, but there's so much more here.

If you like the arts, hitting Symphony on the Prairie in the summer is an awesome time. The ticket price pays for itself because you can take your dinner and have a wonderful picnic before the show. Bring a few bottles of wine and make friends with the people around you. The Indianapolis Symphony is actually pretty awesome altogether and has recently announced a new (young) maestro that will bring a lot to the table in 2012: http://www.indianapolissymphony.org/index.aspx

Our art museum is free and absolutely stunning with newly renovated grounds with amazing installations throughout and wonderful gardens: http://www.imamuseum.org/100acres

They also do outdoor movies on Friday evenings in the summer where you can picnic and watch Goonies, Casablanca, the original King Kong...they always pick fun options.

We're known as the amateur sports capital of the country: we house the NCAA headquarters and museum, have one of the top-ranked minor league baseball stadiums (http://indianapolis.indians.milb.com) in Victory Field, and play host to a lot of the NCAA events (and a lot of Olympic swimming at the IUPUI Natatorium). That's not even mentioning our Colts or (God help 'em) Pacers.

You could walk down Mass Ave and eat at a great restaurant, browse several art galleries, see a play at the Murat (now AWFULLY named the Old National theater or some such atrocity) or a concert at the Rathskellar's Biergarten, and then find plenty of late night places for a drink or tapas. And park for free while doing it!

If you wanted to see some small town living, hit Zionsville or (my personal paradise) Bloomington, IN which is home to Indiana University. Stop by the Oliver Winery on your way down and grab a bottle to drink near the lake and then head into Bloomington to see the much-acclaimed shows at the Jacobs School of Music or eat at some of the top eateries in the state at Farm or Restaurant Tallent. Then hit the Bluebird or the Video Saloon to get a little grungy with the college crowd. Taking a walk through IU's campus is not to be missed either if you're into campuses like I am.

If you EVER have questions about Indianapolis, please don't hesitate to PM me. I love talking up our little city and there's PLENTY to keep you happy and entertaned here. I promise :)

Yes, you're jaded.

I haven't heard anything about Boulder.

Welcome to FlyerTalk ndcollin. :D

+1 all very interesting and quite scenic in places, went for the Warhol museum and stayed to see the rest of the museums as well