Free from the clutches of the Durst house, the party explores the Village of Barovia, and learn that because only Vistani have the power to freely travel to and from Barovia, they control the region's economy; everything's expensive, there are very few choices, and everyone is miserable (it's basically an airport).
Tom buys a pastry from a old woman in the street and it takes him on an incredible trip. Once Thud slaps some sense into him, Grey buys a couple more pastries and kicks off an episode of CSI: Barovia with Brenna, who studies the pastries and determines that they are magical, not pharmaceutical, and that their trip-sending properties dissipate after 24 hours.
In The Blood of the Vine, a Vistani-owned tavern, the party meets Ismark Kolyanovich, the new Burgomaster of Barovia who inherited the title from his late father, Kolyan Indirovich. Kolyan died "from fright" after two visits from Count Strahd von Zarovich, who has taken a romantic interest in Ismark's younger sister, Ireena. Ismark is not well-liked in the community, and has been given the nickname "The Lesser". Given this, along with his father's recent death and the interest that "the devil" has taken in his sister, Ismark has been spending the past few weeks drinking instead of taking over his late father's Burgomasterly duties.
The party agrees to help Ireena and Ismark bury their father at the local church, but when they do they are set upon by (possessed) wolves, who attack everyone except Ireena. Just as it seems like the wolves have been driven back, a familiar black carriage arrives. Still pissed over last night's theft, Tom (with Thud in tow) attacks the driver, who nearly kills them with a look. Only a restraining hand from the man inside the carriage—almost certainly Strahd—keeps his driver from exploding everybody's heads. The party, along with Ireena, Ismark, and the village priest—a wild-eyed, sleep-deprived fellow named Donavich—barricade the church and wait for Strahd to leave.
Father Donavich tells the party that his son, Doru, was killed a year ago when he accompanied another outsider—a wizard—to Castle Ravenloft to kill Strahd. The wizard vanished in the assault and the villagers who accompanied him were slaughtered. Then two weeks ago, Doru returned as a vampire in Strahd's thrall. Donavich was able to trap his son in the church undercroft, but doesn't know what do to next and hasn't slept since (not surprisingly, this has not helped him think of a solution).
Once Strahd departs, Ireena and the party start the journey west to Vallaki, where Ismark believes that his sister may be able to hide from Strahd. Ireena insists that Ismark stay behind and start acting like a Burgomaster, which presumably means helping Father Donavich with his vampiric son, which the party concludes is a problem that can probably wait.
Shaken by his experiences in Barovia thus far, Tom starts firing sunbeams from his palms at anything that approaches the party during their journey. Mostly birds. When the party happens upon a corpse that bears a certain resemblance to both Grey and Ireena, they search it to find another glass orb filled with smoke. Thud—the only one strong enough to pry the orb from the corpse's grip—comes down with a case of the butter fingers, but Brenna is able to reassemble the shattered orb with ease.
Fearing another wolf attack if they camp alone, the party follows the sounds of an actual party to Tser Pool, where a band of Vistani are having a grand old time swapping stories and also bodily fluids. The party members all switch their wallets to their front pockets before joining in the festivities (to varying degrees).
Eventually, the party members are drawn away from the outdoor festivities by Madame Eva, the fortune teller that [[Gregor's family]] gave five stars to on Yelp. She tells the players that they are going to have to take on Strahd if they ever want to leave Barovia, and that she can help them in a vague, frustrating, deck-of-cards-based sort of way…
"This card tells of history. Knowledge of the ancient will help you better understand your enemy… The treasure you seek is hidden behind the sun in the house of a saint."
"This card tells of a powerful force for good and protection, a holy symbol of great hope… I see a sleeping prince, a servant of light and the brother of darkness. The treasure lies with him."
"This is a card of power and strength. It tells of a weapon of vengeance: a sword of sunlight… It is hidden in a small castle beneath a mountain, guarded by amber giants."
"This card sheds light on one who will help you greatly in the battle against darkness… Find the leader of the feathered ones who live among the vines. Though old, he has one more fight left in him."
"Your enemy is a creature of darkness, whose powers are beyond mortality. This card will lead you to him! I see a secret place—a vault of temptation hidden behind a woman of great beauty. The evil waits atop his tower of treasure."