Its definitely November.
Yes January and February suck, but the days are starting to get longer and you can do the outdoor winter stuff like skating and skiing. November literally has nothing going for it.
For me it's as follows:
1. November - see above
2. March - no winter activities, no holidays, just cold or slush every day.
3. January - coming down the holiday high, no holidays other than new year, but at least you're well rested and can go skating outside.
4. February - similar to January, but at least its short, the days are getting longer and theres a holiday in the middle of it.
5. December - Christmas makes it tolerable and winter is in full swing. Its a pretty fun month.
6. August - usually too hot and smoky most days. Its summer though, and the cooler evenings make August amazing when the smoke lets up.
7. April - weather is on and off, but the days are exactly the right length at this point. The +20 degree days that can come in the second half are incredible.
8. June - summer is more or less in full swing, however, the rain for most of the month puts a damper on things. Still, the grass is green, the days are long (probably too long) and everything feels alive.
9. May - the first half is typically just a carry over of April, but the second half usually has the most glorious weather of the year. Long days, crab apple blossoms, green grass ,birds chirping, temps in the mid to high 20s.
10. October - fall is in full swing, Halloween is a blast and the weather is usually decent, especially the first half.
11. July - this is peak summer in Calgary. Super long days, Canada day, stampede, green grass, smoke usually hasn't gotten bad yet.
12. September - temperatures are perfect. Days are the right length. Autumn foliage is at its peak, smoke is usually finished.
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