Piff the Magic Dragon
Piff the Magic Dragon brings his offbeat combination of stand-up comedy and magic to City Winery Boston for an evening of deadpan humor, visual illusions, and absurdist charm. Known for his signature dragon costume and appearances on *America’s Got Talent* and *Penn & Teller: Fool Us*, Piff has been recognized by *Variety* as one of its Top Ten Comics to Watch and has received Best Comedian, Best Magician, and Best Headliner honors at the Best of Las Vegas Awards.
The show also features Mr. Piffles, described as the world’s only magic-performing chihuahua, along with special guest Jade Simone. The performance is presented in City Winery’s intimate setting, with food and wine service available during the show.
When: November 13, 2026
Showtimes: Piff’s Private Party package begins at 5:00 PM. Doors open at 5:30 PM, and the main performance starts at 7:00 PM.
Venue: Main Stage, City Winery Boston, 80 Beverly Street, Boston, MA 02114
Tickets: Starting at $54.00
Lineup: Piff the Magic Dragon, Mr. Piffles, and special guest Jade Simone
Piff’s Private Party: The package includes a laminate and lanyard, wristband, signed poster, a photo opportunity with Piff, Mr. Piffles, and/or Jade, the chance to record a shout-out video from Piff, an opportunity to win a stuffed Mr. Piffles, and a one-on-one magic trick.
Dining: Food and beverages can be ordered at your table during the show. Guests may also arrive early for a meal in the restaurant, where reservations are encouraged through Resy beginning one month before the performance.
Wine service: Guests can reserve a preferred bottle in advance so it will be waiting at their table when they arrive.
Venue policy: City Winery does not require a two-item food or beverage minimum, but strongly encourages each guest to purchase two items to support the venue staff, service, artists, and production.
Membership: Vinofile members receive 48-hour early access to new shows, no ticket fees, and points that can be exchanged for complimentary tickets. Vinofile VIP+ members receive additional wine benefits.