So, some info of what is going on.

For the last two weeks on a daily basis with a group of friends on Discord and Roll20, that i convinced to play D&D ( and that they enjoy it very much) we're running Curse of Strahd, i'm Dming it, since i was the only one that had the most recent experience in DMing( was doing some Pathfinder Dming and some 4th Ed Dming before).

Now the band as, because of me messing up with the order of things, gone to Argynvostholt, even though they're only lvl5, now there is 6 characters( and thats counting once NPC that i control, that serves as the tank, since the real tank guy is absent since last week, and another dude that made a character, but still couldn't find the time to join), so while i was concerned, they're fine for now( plus when i try to hit them with the mobs, i have a hit% of like 15%...).

But knowing them, i know for certainty that they will never go to Stradh castle until they're at least lvl 9 or above, so the whole arc with Argynvost skull is going down the drain kinda.

So i had this idea, and its something that i saw somepoeple do, to have them figth a raised Argynvost.

Now, some of those that i saw, simply put the Dragon someplace in the wilds or guarding a place...

I had another idea, since they still have to go back to Vallaki for the festival( they started as a traveling band of Jesters, musicians and Carnival, so of course they where invited by Vallaki Burgomester to participate in the festival event), and even though they resolved the St Andrals relics quest, i kinda tweeked it, since the room in wich the Relic was was bombarded with Fireball spells by the Draconic Sorceror because of the Vampire spawns( after they scattered because of the turn Undead of the Cleric) i kinda decided that the Relic was badly dammaged, but they still brough it back.

And since there was still no occasion where they've met Strahd, i thouhg that the St Andrals feast event was the perfect spot for this plan of mine.

Since the Relic of St Andral's is badly damaged, its power is greatly diminished, at best it can cast a 20feet sphere perpetual sanctuary around it.

During the event, Strahd will of couree appear as it is supposed to be, but as a taunt, he will come with Argynvost skull, talking about their visit to the Mansion, then use is animate Dead to raise a Skeleton Dragon( used a young Silver Dragon profile with Dracolich resistances and immunities)

WHile the City guards will be occupied with the Wolves and Vampire Spawns, the party will have to deal with the Skeleton Dragon,also i added a "boss fight" mecanic, that when the Dragon is reduced to 100 hp he summons 1D4 Flameskulls( i've toned them down a bit, only 20Hp, no rejuvenation and spellcasting trait) and another 1D4 when he's donw to 50hp.

I hope it will give them an interesting fight, and make them soil their pants a bit, since the start of the module they din't had an hard enough time to the point where none of them ever felt unconcious( well 6-7 people in a module made for 4-5, kinda mitigate things, and they're pretty good to come up with tactics).

It will also establish Strahd as the BBeG that he is to the party, since they've only heard about him.

So any advice? i plan on the fight to first take place in the church, with the Dragon busting his way through the walls, and maybe when the Dragon hits a certain HP treshold having him fly up and devastate some of the city's houses and fly by Smaug style in the Hobbit, before finishing the fight in the city streets.

Or the other way around, having the Dragon wreck havocs around town, having them fight off a small group of Vampire spawns, then having the Dragon land on top of the church, busting his way through and them facing it.

Yeah i think it works best like this, more climatic, i also have some audio files ready to really amp things up, some jurrasic park Trex roars for the dragon, Vincent Price laughing from Thriller when Strahd comes and go and more...( since the geek levels are high, we use the FF7 fanfare when they finish a fight...)

Dragon profil; https://www.dndbeyond.com/monsters/151649-skeleton-dragon

Seems like an okay monster.

I see your points, now on the power level of the group, to put it simply the 6 Vampire spawns from the Coffin maker shop, was hardly a fight for them, it just took long because the rogue of the party tried to go solo and do some stuff on his own in another part of the house and he has a tendency to flee combat and leave the others.

Even so, they where rarely in any danger, Heck they even wiped the floor with the Revenants from Argynvostholt and 3 of them allready has silvered weapons( since you can loot a couple in some places of the module and since there was nothing about it, i allowed the fighter to silver his longsword at the weaponsmith)

And the others use extensivly magical attacks and one of them is an Hexblade warlock with improved pact blade, so in regards to magical resistance, they're set...

Also since they've looted the Vampire slayer kit from Rictavio's wagon, they have 4-6 vials of holy water, and there is one paladin and one cleric, so that not really a problem for them...

Also like i said, i watered down the Flameskulls, so that they only have 20hp, and they don't have the rejuvenation and spellcasting traits, so no need for holy water to destroy them.

St Andrals feast will be the very first time where the party encounter Strahd, while they won't fight him this time, it will be sure to encounter them on more occasions in the futur, this will only be the first time they get to see him, not the last.

Yeah the Weaponsmith is my mistake, when they asked if there was one, it seemed like a natural thing, only by a logical stand point, since the poeple in town will need iron tools for some of their daily routine.

And someone would be in charge to make the weapons and gear for the City Guards, so when they asked about it i "went yeah sure, let me check a sec....*under my breath* oh crap..."

Then i just went with it, thinking "oh what the heck..." now to avoid too much the smith only had enough silver that could be used for 2 weapons at 3 times the price.

They've found a silvered shortsword in Rictario's wagon cache, with the "vampire slayer kit", so on a party of 6, 4 of them have silvered weapons, one has an improved pact weapon( hexblade) and another one is a Draconic sorceror so he doesn't really care for melee weapons and just fire blast away at anything...

The Flameskull was more to stay on the "Bone" theme of the whole fight, and i wanted something that could force them to change tactics then simply "run up to the dragon and smack it".

Wich in the end worked wonders.

So i'll make it short, the Fight was intense, 2 of them fell unconcious but they managed to get them up, 1 nearly died, the rogue who had the habit of leaving everyone fighting and just go on his merry way doing something else, had to deal with the Flameskulls and actually contribute to the fight for a change.

They've loved the fight, though it was pretty cool, but nerve wracking.

Things went down like this, after they encountered Vladimir in Argynvosyholt and found the piece of Argynvost journal, they came back to town, took some time to make some stuff here and there then took a long rest.

They where waken up by sounds of alarm and people panicking, someone yelling something about Vampires attacking the church.

They went straight to the church, seeing the guards fighting off wolves and bat swarms in the streets and helping the civilians to escape.

They arrived at the church, saw the place with Vampire spawns all around, made a break through, to see the figure of Strahd hovering above where the priest and some civilians took refuge in the 25ft bubble cast by the remains of the Relic.

Strahd greeted them, saying that they gave him much enjoyement, i had him talk about events "he witnesed" them do and found it amusing in this boring land.

Then He spoke about their visite to Argynvostholt, asked how that Old sack of worms and flesh Vladimir was doing, then spoke of Argynvost skull, where he pulled the Skull out of thin air, hovering in his hand and asked them with a taunt " Are you looking for this perhaps?" he then throwed the Skull in the cemetary and cast Animate Dead( i know its not exactly how its supposed to work, but it was just for this), and they saw all the bones in the graveyard burst out of the tombs and aggregate with the dragon skull to form the Skeleton dragon.

The Dragon then proceeds to make damage to the city and the party went after it.

Once they'de attacked the dragon at range for enough dmg, the Dragon landed and released his Breath attack, wich made the Party really wary of the Beast power.

Once they've defeated the Dragon, they rushed back to the church, to find Strahd trying to force its way through the shield of light from the relic, seeing them beaten but still alive he found it amusing, saying something like" maybe you'll proof yourselfs usefull after all,...you amuse me, your pitifull efforts are worth the laugh" at wich point the Goliath fighter of the party charged Strahd and managed to land a DOUBLE crit with dual wielding, wich Strahd found "invigorating" and then told them that for this time he will take his leave, but that they're invited to his Castle if they want to drop by, laughing in teh Shadows( used Vincent Price laughing audio) and dissapearing in a Swarm of Bats.

And thats where we ended the session, tommorow they'll have to deal with the after math of the battle.

While in the module the poeple revolt and stone to death the Burgomester, i think i'll let them the chance to talk the crowd out of it with conditions, and let the festival happen, since they're looking forward to it to make their show( they plan to make a theatrical retelling of their adventures from the House of Death to the Oldbone grinder, with musical acts from the Bard and some pyrotechnics from the sorceror)

In the end the Dragon was on the right powerlevel, the Flameskull Adds worked great to put some pressure on them and make them think outside the box, wich was rewarding not only for them but also for me.

The fight took a good 2h30 to resolve, wich i feel is long enough for a Boss fight, and with this boss fight and the acquisition of the Skull they had enough XP to go up to lvl6, so they're quite happy with how things went.

This sounds awesome well done.