For classical music and art I'd put Cincinnati up against any city in the US. Professionally you have The Cincinnati Symphony and the Cincinnati Opera. You also have the University of Cincinnati's College Conservatory of Music and the School for Performing Arts. The Art Museum and Taft Museum are both worth a visit.

A visit to the Santa Fe Opera coupled with museums, history and fabulous scenery could be a real treat for you.

Happy travels!

Cleveland is also great on classical music and art with the Cleveland Orchestra and the Cleveland Museum of Art. Great ethnic neighborhoods, too. And some very, very good restaurants.

LOL I like Cincy just fine, but that statement is crazy. The mayor of Cincy wouldn't argue that Cincy could rival NYC in terms of classical music and art.

Nor would I. The OP was asking about small or medium size cities.

Hmmm...an interesting thread here.

These are places that we have been to and want to return to in our travels (some may be smaller than wished):

Bend, OR-- beer, whitewater, fly fishing, skiing and some pretty good eats.
Santa Fe NM-- four visits and we never get enough time there.
Bozeman, MT: outdoor sports, beer, not just a college town.
Tacoma, WA: glass museum, interesting DT and a big park (Pt. Defiance)
Bakersfield, CA: Hispanic meets cowboy, sprawled out but intriguing.
Flagstaff, AZ; old west, Grand Canyon
Tucson, AZ, not just a college town and not very small
Albuequerqe, NM, great food, used bookstores and a nice museum or two
Spokane, WA; food, four seasons, nice older downtown
Sandpoint, ID; food, setting & some very nice locals
Key West, FL, go when the cruise ships don't dock there

I like Des Moines, Iowa. The Court Ave district has some nice restaurants and brewpubs, plus there are running and biking trails, and a very nice art museum.

one can look for Omaha and Milwaukee

This thread got me to start thinking about all the cities I've been to. My short list that I would go back to are:

Medium:
Portland, OR
Victoria, BC
Charleston, SC
Savannah, GA
Spokane, WA

Small:
Walla Walla, WA
Dayton, OH
Cheyenne, WY
Halifax, NS (or is it medium.. I don't care, I'd go back!)
Estes Park, CO (it's a bit of a drive from Denver, but if you go to the Scottish Festival it is awesome!)

Reno/Lake Tahoe
Boulder, CO
Ann Arbor, MI

santa cruz, ca

Eugene Oregon

Ottawa Canada

Really? Boulder?! Sure it has it's charm, but it's also full of bums and burnt out hippies waiting for the magic peace bus to take them to the promised lands. Of course I live 14 miles outside of the city, so maybe I'm jaded.

I agree with the poster above the MKE is probably more exciting than MSN, but timing is everything. If you could make it during a football game things are much more lively in Madison (a nice saturday would be spent at the farmer's market at the capitol early in the day, the football game later in the day and the bars at night). That being said, Milwaukee, being a larger city, has more culture, much better museums, and more interesting neighborhoods.

Some other cities I'd recommend:

Santa Fe, NM
Portland, OR
anywhere in Vermont (though any city would be on the small side)
Memphis, TN can be pretty fun
Ottawa, Canada
Quebec City, Canada

Interesting and great suggestions. I think the ones that jump out at me the most that I've seen mentioned multiple times are Kansas City, Halifax, and Portland ME, so that should be a great start.

I was surprised to see Spokane mentioned a few times - it's a city I've never really paid much attention to. The last time I was there I was about 13 years old and we just spent the night at some cheap hotel. I don't remember being particularly impressed - but what 13-year old can be impressed?

Is there a penance I can do for saying the best barbecue I've had was in St. Louis? I did have some great barbecue in Nashville a few years ago...

13 years ago Spokane was a dump, but they have really turned themselves around. Downtown is very nice and the river walk is wonderful, especially the bridge overlooking the falls. There are some great small hotels there, so I wouldn't ever recommend a chain hotel. I loved the Hotel Lusso and there is another whose name escapes me on the opposite corner.

I think in penance for saying the best barbecue was in St Louis you should do a MR to all the barbecue hot spots. So, you are sentenced to fly to Memphis, Kansas City, Columbia, SC, Dallas, and.... I think I need some others to chime in. Anyway, you must go to all of them and eat barbecue in each city at a famous location.