I'm currently working on an addon to Wet and Cold for my last mod for Skyrim which features lore-friendly holidays that follow the in-game calendar.
Current holidays planned from my messy brainstorming notepad:
Spoiler
New Life Festival - Morning Star 1st
Food
South Winds Prayer - Morning Star 15th
More people in temples
Festival of Lights - Morning Star 16th
Lights in Dawnstar
Feast of the Dead - Sun's Dawn 13th
Food in Windhelm
Heart's Day - Sun's Dawn 16th
Inns free, more people in inns? heart decorations?
First Planting - First Seed 7th
More crop supplies, more people in temples
Second Planting - Second Seed 9th
" "
Mid Year Celebration - Mid Year 16th
More people in temples. people in dungeons?
Merchant's Festival - Sun's Height 10th
More people in shops, prices half off (possible?)
Sun's Rest - Sun's Height 20th
All shops closed
Harvest's End - Last Seed 27th
Food everywhere, free drinks in inns
Tales and Tallows - Hearth Fire 3rd
Dead walk at night
Witches Festival - Frostfall 13th
Demonologists, conjurors, lamias, warlocks, and thaumaturgists meet in the wilderness outside, summons
Warriors Festival - Sun's Dusk 20th
Warriors, spellswords, rogues go to equipment stores and blacksmiths. All weapons half off (possible?). Kids with swords.
North Winds Prayer - Evening Star 15th
More people in temples
Old Life Festival - Evening Star 30th/31st
More people in temples, taverns
Alduin's Defeat
Date set when you defeat Alduin
Liberation/Reunification of Skyrim
Date set when the civil war ends
Most of the holidays will have basic decorations set up on the day such as lanterns and candles. I'm going to avoid adding NPCs and instead use the method from Wet and Cold/Run For Your Lives to move already present NPCs to appropriate locations. Mods which populate Skyrim with NPCs will be recommended. I may also use the equipment switching from Wet and Cold to modify outfits (such as festive hats, toy swords).
I currently have non-merchant NPCs crowding into temples throughout the day and it works fine. After 5pm the rest close their shops early and join them, which is pretty neat. I thought I'd have more trouble setting that up but it works well. As usual compatibility shouldn't be too much of an issue as I won't be modifying NPCs directly and unless a city/village mod is moving buildings around, there shouldn't be many issues with decorations either.
Anyways I'm posting this to gather feedback, ideas, city-specific lore stuff I may not be aware of. Everything I posted is subject to change. The plan was to get this released before the holidays but I'm not sure if that will happen as I prefer to release my mods fully fleshed out.