I feel as though we it would be helpful to narrow the parameters. Town size - maybe 1000-30,000. Smaller than that is really a village, larger than that, it's really a small city.
OP could run separate poll for small cities - say 30,000-100,000. But Reno has already captured the motto of that category - the Biggest Little City in the World.
There are a ton of picturesque small towns in the Pacific Northwest that could qualify, and many have gorgeous scenery to boot (think of North Bend (Twin Peaks locale)) BUT - winters are consistently very dark, and very damp. East of the Cascades, it's drier, but it can also be very cool to very cold during winter.
The Southeast has lots of small picturesque towns that could be very charming in the winter, but that 5 month season of unbearable heat and humidity is a no-go.
So, high-elevation towns of the southeast might be ok - places like Boone, NC, or Sparta, NC, or Dillard, Ga are cooler in summer, not too brutally cold in winter.
In the West, someplace like Sedona would be hard to beat for weather and scenery. Guerneville has its charms too, besides being a gay town. But it's very prone to flooding on the Russian River. I've never been there, but some people seem to find Bisbee, Az very charming. Julian, in the mountains outside of San Diego has a lovely climate and is very picturesque.
Most of these places are quite isolated geographically, so they would not be appealing to anyone who needs to be near a big city for the cultural offerings - of the MEN