In 2022, well into the explosion of online Table Top RPGs, and just after things had started to open up again post-pandemic, one of our local-ish theatre companies, Driftwood, did a combined live and streamed Dungeons & Dragons game as a fundraiser. It was a ton of fun to attend, and hilarious to watch a bunch of actors (only about half of whom seemed to have played D&D before) play an adventure based on some of The Bard’s most amusing bits.

The Dungeon Master for the game was Jeremy Smith, Driftwood’s Artistic Director. He put together a one-shot adventure that was at least as entertaining to watch as it must have been to play. But that’s not really what this post is about. At that time, Jeremy and his wife were the proud new owners of the Gillespie House B&B in Picton, busy renovating and planning their new adventure. They put up a weekend of D&D at their new B&B in the fundraiser auction that accompanied the event. My parter an I had to get that weekend, and so bid appropriately. This past February we finally scheduled the weekend away, and invited along some friends of ours that also play.

Given that he put up a weekend of gaming in an auction, it should come as no surprise that Jeremy is a long-time D&D player. Nor should it be a surprise that his gaming and theatre experience should compliment each other. As a result, we had a fantastic weekend playing an original adventure Jeremy had written specifically for his B&B guests.

The pre-made characters he gave us to choose from were all interesting, and complimentary, and had a few details left for us to fill in to make them our own. The story was clever, with well placed beats, and it became clear discussing the game with him later that he was tailoring the balance of combat and role playing to our group’s play style.

The B&B weekend itself was also fantastic. Their house is beautiful and comfortable, the meals were fantastic, and our game sessions were well supplied with snacks and treats.

As of this past summer, Gillespie House is now open to the public again, and their D&D B&B add-on available to guests. We’ll be there again this coming winter, sometime when we need a weekend away.

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