Running a long-form Dungeons & Dragons campaign means constantly balancing tone. Some nights lean into eerie mysteries, others into laughter, and every so often the table walks a fine line between both. Session 17 of our Waterdeep: Dragon Heist campaign — “Orchard of Masks” — was exactly that: the first steps into the Emerald Enclave’s Dark Harvest quest, with equal parts farce, tension, and foreboding.

Setting Out from Trollskull Manor

The morning began in classic Trollskull fashion: Doc and Maple bickering over orange juice “quality control,” Clover tuning strings upstairs, and Raven reminding everyone that, no, they did not need a dog — they already had three children under their care.

Eventually Kiril gathered the group and steered them toward business. The Emerald Enclave had reported trouble with scarecrows in the farmlands south of the city. So, while Raven and Clover stayed behind, Doc, Maple, and Kiril made their way through Waterdeep’s bustling southern wards, bound for the River Gate.

Passing out of the city stirred old memories for Doc, but no one stopped them. The air changed from city smoke to vineyard wind as the skyline gave way to open farmland. A crossroads presented three names: Snobeedle Orchard & Meadery, Stoutfellow Farm, and Amendsfarm. The players put the pieces together: the Stoutfellows were new money, rising fast; the Snobeedles, old roots with polish. Either could be tied to the scarecrow stories. But the dice — and Doc’s gut — pointed them to the Snobeedles first.

A Wagon in the Mud

On the road they encountered a wagon bogged down in muck. The driver looked ready to be stuck all day. After Doc’s characteristic attempt to barter help for a dog, the group pushed, pulled, and freed the wagon. The driver muttered gratitude, then offered a pointed comment: the Snobeedles were “a nasty bunch of halflings.”

Doc noticed the barrels bore Stoutfellow Farm branding. Bias, then. Interesting. If anything, it cemented the party’s choice to see the Snobeedles for themselves.

The Orchard Too Perfect

The Snobeedle Orchard was immaculate. Rows of fruit trees stood in sharp, geometric precision. Whitewashed walls gleamed. A gilded sign swung without a squeak. Even the scarecrows had scarves tied in fashionable knots. It was beauty curated into something uncanny — as if the orchard were performing wealth rather than living it.

The meadery inside carried the same veneer: trophy bottles lined up like prizes, attendants moving with rehearsed precision. The party was offered drinks, and for a moment it seemed they would slip easily into polite conversation.

Dogs and Crossbows

Then Doc asked if he could have one of the Snobeedle dogs.

Not buy one. Not adopt one. Just take one.

The bartender stiffened, hand drifting to a crossbow beneath the counter. Maple tried diplomacy, Kiril tested dry humor, but Doc doubled down, eyeing the dogs like he was choosing cuts at a butcher’s stall.

The room tilted toward violence. A bolt was notched, and when Kiril told the bartender to go ahead and make Doc into a pincushion, she very nearly did. The bolt flew, missing Doc, but enough to set every player at the table straight in their chairs.

To their credit, Maple and Kiril pulled the mood back from the edge. Charm, patience, and a few high rolls calmed the Snobeedle attendant, who put the crossbow away as if nothing had happened and smoothly returned to offering drinks. Doc, muttering about injustice and dogs, stormed off toward Waterdeep, leaving his companions to continue the investigation without him.

Closing Thoughts

This session pushed the group deeper into Dark Harvest while reminding us how unpredictable the path can be. What began with laughter about juice ended with a crossbow quarrel in a gilded meadery. And beneath it all, the players are beginning to feel the tension: why are scarecrows walking in Undercliff? Why do the Snobeedles polish their orchard into a mask? And what secrets lie in the fields beyond?

Next time, those questions may find sharper answers.