Hosting a Festival
Why would holidays be important in D&D? What purpose could they possibly serve in the campaign? As a DM, why bother putting work in something like that when you have this huge story and world and all you really want is to have the party finally face the big bad you spent sooooo long creating?
Because Dungeon Crawls are Exhausting
I’ve played in tabletop games that were just constant dungeon crawls and battles and, well, they’re exhausting. Not just to the characters, but to the players too. I remember stuffing my PHB into my backpack and making sure I had my dice and wondering if it would really matter if I even showed up because I didn’t want to do the same thing the party had been doing for the last 3 games. Dungeon crawls are long and rough and sometimes the characters can’t rest and therefore the magic users run out of magic and cannot recharge. Hit points get low and can’t be replenished. When you come out the other side, victorious and bedraggled, with your loot and XP, looking forward to leveling up, do you want to go straight into another fight? Or do you want to let your character rest? Maybe read a tome you found that will increase your intelligence, attune to a magical weapon, get those darn hit points back. Update your character sheet because you just leveled up. Or party.
Decompression
As a DM, I find one of the best things I can present to my players as a way for characters to decompress, is holiday or a festival. I make up most of them based on pagan holidays because they’re easy. Winter and summer solstice and all that. In the campaign I’m running right now, I’ve based it off my own world with my own pantheon so I’ve created holidays and festivals honoring those gods, as well as harvest and spring festivals. Sometimes I throw in something new and fresh in a small town or village that’s specific to the area/region. It gives players the opportunity to relax, get a little R&R. If a player wants to spend time updating their character sheet, they can, if they want to go buy stuff from a local shop to replenish their stock of healing potions, they can, if they want to use their skills to bob for apples, race, throw logs, or enter archery contests, they can. It gives them time away from each other and the DM has the opportunity to focus on character’s personal growth, as well as pull in elements from their backgrounds. It’s also the perfect setting to throw in a side-quest.
A Perfect Setting for Disasters
The other thing holidays and festivals are good for in game… disasters. Tragedy is always worse and harder if it happens on a holiday. A life lost is tragic, but a life lost on a holiday will make the news. The news is sadistic like that, isn’t it? On another note, that holiday is forever ruined for the loved ones of the person lost. This is no different in a game. A village attacked is awful, but the worst is when a party comes upon a slaughter and see the maypoles or giving trees. Or blood and bodies among the now cold feast still set upon the tables. I ran a game for my sister and her friends one summer (all girl game) I could NOT get those girls out of the darn town to adventure. Mind you these were 8th ad 9th graders, a few of which were cheerleaders (seriously, not kidding. It was weird). All they wanted to know was how cute the town guards were and whether or not they had a chance to go on dates with them. So I threw together a festival and they had dates with some cute guards. And at night, while a parade was marching down the streets and sweets were being thrown to children, the town was attacked by orks. Much of the town burned to the ground. People were slaughtered and enslaved, the cute guards who the girls had spent so much time trying to dazzle were killed defending the people. And if THAT didn’t send those girls on a rampage… They became the harbingers of death, even taking their vengeance to levels I hadn’t expected at all from a bunch of high school girls.
Cute blonde still in her pleated cheer skirt because she was gaming after practice: “I dig his eyeball out of his head with a dull butter knife!”
Me: “Wait… really?”
My sister: “Yeah, do it. He’ll give us a better price on armor then. We need it to go after the hoard.”
The sweet one of the group: “Oh! I’ll cut off his toes!”
Me: “Girls! He’s a shopkeeper!”
Cheerleader: “Shouldn’t have thought he could take advantage of us because we’re girls.”
Me: “Those are standard prices for masterwork armor!”
Players: “…”
Me: “…”
Cheerleader: “Please forgive us, kind shopkeeper, our town was destroyed not long ago by orks, during the Festival of Harvests. All of our boyfriends were killed. We are on edge.”
The sweet one: “So… we’re not torturing him for better prices?” (Said with her dagger poised above the shop keepers toes)
Seriously, nothing gets a party to work together and/or adventure quite like tragedy on a holiday
Four Seasons of Epic Fantasy 