New Year's Day (January)
MLK Jr. (January)
Presidents' Day (February)
Valentine's Day (February)--celebration, not really a holiday
St. Patrick's Day (March)--celebration, not really a holiday
Passover (March/April)--no days off from work
Easter (March/April)--a lot of Catholics I know take Good Friday off, but it's not really given
Mothers' Day (May)--not a holiday, but you'd better treat your mom/mother of your children right
Memorial Day (May)
Fathers' Day (June)--not a holiday; has always felt like a make-up for Mothers' Day, and kind of forced.
Juneteenth (June)
Independence Day (July)
Labor Day (September)
Jewish high holidays: Yom Kippur and Rosh Hashanah (Sept/Oct)--no days off from work
Columbus/Indigenous People's Day(October)--can't remember ever getting this off
Halloween (October)--not a holiday, but the best celebration
Veterans' Day (November)--rarely get this day off; can't remember the last time
Thanksgiving (November)
Chanukah (December)--no days off from work
Christmas (December)
On that basis, for me, it is
(1) January because there are two holidays--and New Year's Day is awesome thanks to college football and bad food. Having MLK day during a gloomy month is nice.
Then I go (2) December because even through Christmas is only technically one day off, I almost always get a couple days around it, plus my birthday is squeezed in there, and normally my litigation calendar isn't too busy. And the New Year's celebration starts in December.
(3) November because Thanksgiving is awesome, and a four-day weekend is always lovely. Plus Veterans' Day (though I never get it off, which annoys me).
(4) July: Independence Day feels like it often ends up more than just a day. Maybe I'm wrong, but it feels that way.
(5) May: Memorial Day is the civic holiday I care the most about, and it comes after what feels like a long stretch of no extra days off.
(6) February: Presidents' Day among a 28-day month makes the month go faster.
(7) September: because Labor Day is nice. BRAD, I laughed out loud about your communist remark. I don't think you need to be a commie to appreciate the middle class Americans that built this country...but maybe I'm wrong? Even though it comes a pretty long time after Independence Day, there are often summer vacations in there that make it seem not that long.
(8) June: Juneteenth comes pretty quick after Memorial Day, and shortly before Independence Day--it's nice to get the day off, but I would rather have it in...
(9) October: has a day that is a holiday for banks and maybe schools? But I never get it, so it pisses me off, regardless of its name, more often than not.
(10) April: because I think that's when Easter falls most often. No days off, but Good Friday is usually pretty chill at work, and we generally put some effort into a family gathering on Easter. Bonus points for aligning with Passover for people of that persuasion.
(11) March: sometimes gets Easter/Good Friday/Passover. Normally doesn't. St. Patty's Day isn't a holiday, it's just an excuse for amateurs to drink badly.
(12) August: no holidays, but summer vacation often bleeds into August, so it's ok.