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It is very difficult to predict what your experience will be like. Mostly it depends on what you're wanting to see.
Our winter season generally begins around the beginning of November (usually by the time October 31 rolls around we start seeing frost or light snow on the ground at night)
Our winter season is never dominated by unending snow, and that's why it's difficult to predict what it will be like. Throughout the winter, it's possible to have a bright and sunny 60+ degree day followed by a snowfall the next morning. Our snow tends to melt pretty quickly after it falls, though.
Higher elevations may be more difficult in the winter. For example, if there are snow warnings on TV and you are not used to driving in snow, do not attempt to make the trip between Colorado Springs and Denver.
If you want to come, feel free! You'll probably have a great time no matter what time of the year you come. If you have enough time to stay, you should probably have plenty of hours throughout most days to do sightseeing. Keep in mind that Colorado Springs receives 300 days of sunshine a year, and we often have plenty of sunny days in the winter.
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