I'm like you - don't play often, been DMing CoS for two years, I used the entries for "Rictavio's Journal" on page 102 as inspiration for strange tales from lands afar. Other suggestions may include drawing on Forgotten Realms, Dragonlance and Greyhawk novels, the works of Tolkien and even possibly Greek Mythology? What about some randomly generated inspirations from pages 72-75 of the DMG?
My Rictavio is an orator as well, with a strange, uncomfortable manner and a wacky sense of humor. I saw the character as an opportunity to break the tension at key points, per the "Marks of Horror" notes on page 7 - the sentence that "There are no stranger bedfellows than horror and humour", really struck a chord with me. I had him be the center stage act during the opening for the Festival of the White Sun which (following Izek's elimination at the hands of the PCs a day earlier) was followed by a coup by Fiona Wachter and her mob of cultists. For your reading pleasure, a lot here borrowed from other comedic sources, lets just say the PCs were getting increasingly nervous as the act progressed:
The Carnival:
The doors to the carnival wagon abutting the stage burst open and the colourfully dressed half-elf bard emerges with the fanfare of a trained performer.
“Well met, oh wonderful people of Vallaki. I welcome you with much pleasure to Rictavio’s Carnival of Wonders. I, of course am your humble but most jovial host, Rictavio! Before this show begins, allow me to take this opportunity to thank you, the people of Vallaki for allowing me to live among you, to share your food, your wine and your hospitality. And I would most of all, like to thank your wise and joy-driven Burgomaster, the Baron Vargas Vallakovich and his cheerfully captivating wife, the Baroness Lydia Petrovna, for inviting me to perform here today and spread joy to your hearts."
Rictavio claps twice and a high pitched animalistic screech sounds out as a small monkey wearing a pink ballerina tutu hops from shoulder to shoulder of unsuspecting townsfolk before leaping onto the stage and climbing up to the half-elf entertainer's outstretched arm. The bard bellows joyfully,
"Allow me to introduce my trusted assistant, Piccolo! He is a very friendly fellow and exceptionally clever, having accompanied me on many adventures in distant lands."
Rictavio moves back towards the wagon and retrieves a tall stool and a small drum which he sets near the front of the stage. Piccolo leaps to the stool, raises his hands over the drum and turns to watch his master in anticipation.
"Much like the Baron and Baroness, I hold the greatest hope that for every man, woman and child in this unique town, All will be well! I say this town is unique for I have travelled many distant lands yet never found it’s like. I was in the Village of Barovia last week when I heard the priest there had recently opened a new cemetery. People are just dying to get in!"
Piccolo thumps the drum twice and screeches joyfully. Rictavio lets out a gleeful giggle and resumes,
"The undertaker in Barovia had to take a break last night. He couldn’t stop coffin!"
On cue, Piccolo thumps his drum again and the audience appears more bewildered than entertained.
"Their tavern is such a strange place. I was watching two married vampires having a drink when the husband points at the bar keep and asks his wife, “are you going to finish that?”
Piccolo's drums and screeches are drowned out by a single outburst of outlandishly loud laughter from the Baron seated on his make-shift throne. The Baroness joins in after a short pause, her mirth unpersuasively mimicking that of her husband. Rictavio bows to the Baron and continues,
"Close by there was a skeleton waiting to be served. and the bar keep asked him “what can I get you?” To which the skeleton replied, “a mug of ale and a mop please”.
Then a zombie walked into the bar... and into a chair and a table."
The Baron stands in an attempt to amplify his laughter, his wife following suit. He notices the lack of participation from the rest of the crowd and turns to face them, at which point the townsfolk begin to forcibly chortle and snigger. Rictavio spurs the audience and carries on,
"On my way back to Vallaki my wagon broke an axle. I was trying to fix it when the same zombie stumbled out of the forest and offered to help. So it gave me a hand... and an arm and a leg.
Yes the roads are rather dangerous here. A short while later I was accosted by bandits. And before they mugged me, they said “Tell us a joke”. To which I replied, “No thank you, I don’t like tough crowds”.
I arrived at the gates of this brightly joyful town and was greeted by wolf heads on pikes. They looked receptive so I told them some jokes and they giggled a little. Oh I’m just being modest, they loved me! I actually had them howling all night!!
I must say I adore the Inn here. I found out it was haunted until recently when the resident ghost left quite suddenly. Apparently it went looking for stronger spirits!
The guest in the room next to mine is a flesh golem. He thinks I’m hilarious. I can tell - he’s always in stitches!
But at least we appear to be safe from Count Strahd here in Vallaki, I’ve heard he can be a real pain in the neck!"
The Baron's laughter comes to an abrupt end. The townsfolk follow suit. Only the Baroness continues her meek giggle, seemingly oblivious to the sound of her own foolishness. Rictavio appears unfazed,
"I feel rather sorry for the Dark Lord actually, being a vampire wasn’t his first vocation of choice, I heard he wanted to be a theatre actor. But he just couldn’t find a role he could really sink his teeth into.
I’ve also heard he considers himself a great artist. Yes, apparently he likes to draw blood!
I actually met him once you know. On reflection, he doesn’t seem that frightening."
Lightning strikes some distance out of town and thunder resounds across the valley, whilst the crowd grows increasingly uneasy. Rictavio pauses momentarily then declares,
"Oooh, that sounded rather close! Let’s hope the weather holds out a little longer. The fog is so thick here they say you can grab it with your bare hands. I tried yesterday but I mist.
But enough about me, you’re a wonderful audience so let’s make this worth your while. Let’s get on with the show!"
The Baron resumes his laughter and applause with his wife and the townsfolk joining him in a half-hearted wave of mock-laughter and clapping.
"For my first act, I'm going to need a volunteer."
<Insert acts in sequence involving the PCs. A little while later...>
A soft drizzle starts to fall and the Baron stands, then moves to mount his horse. He scans the crowd nervously before motioning to one of the guards to hand him a lit torch with a long handle.
"People of Vallaki, the time has come to set the sun ablaze!".
He moves his horse through the crowd with little consideration as to whether the citizens are parting quickly enough before him. Grunts of discontent sift through the townsfolk as the Baron spurs his horse onward, heading for the tower of timber and wicker. Before the makeshift sun can be set ablaze, the sky tears open in a sudden downpour.
“All will be well!”
The Burgomaster cries out with vigil as he brandishes his long, sputtering torch and marches defiantly through the rain towards the wicker ball, only to have his torch go out as he thrusts it into the sphere. A singular laugh erupts from the crowd, drawing the Burgomaster’s fiery gaze as well as gasps from the townsfolk...
Hope you enjoyed reading that as much as I enjoyed role playing it.