Boston Comedy Festival Comedy Contest Preliminary Round 3
Boston Comedy Festival Comedy Contest Preliminary Round 3 brings 12 stand-up comedians to City Winery Boston as they compete for a place in the semifinals. The broader competition features 96 comedians from across the United States and occasionally Canada, competing over eight preliminary rounds for 32 semifinal spots and a share of $7,000 in prize money. The lineup is designed to showcase both established performers and comedians who may be on the verge of a major breakthrough.
The show is hosted by Carolyn Plummer, whose comedy draws humor from everyday frustrations, awkward situations, and ordinary experiences. Special guest headliner Demetrius “Big D” Hullum is a Boston comedian with more than nine years of stand-up experience. He has been a finalist in the Boston Comedy Festival and Northwest Comedy Festival, performed at the Netflix Is a Joke Festival in Los Angeles, and hosted national headliners including Sam Jay at the Wilbur Theatre.
When: November 11, 2026
Showtime: 7:30 PM
Doors: 6:00 PM
Tickets: General admission is $25 in advance or $30 on the day of the show. Standing-room tickets are $30 in advance or $35 on the day of the show. The page lists tickets as starting at $30.
Lineup: Carolyn Plummer, host; Demetrius “Big D” Hullum, special guest headliner; plus 12 comedians competing for a place in the semifinals.
Competition: Eight preliminary rounds feature 12 comedians each. The competition awards $7,000 in prize money, with 32 comedians advancing to the semifinals.
Venue: Haymarket Lounge at City Winery Boston, 80 Beverly Street, Boston, MA 02114
Dining: Food and beverage service is available at tables during the show. Guests may also arrive early to dine in the restaurant, where reservations are encouraged through Resy beginning one month before the show.
Venue policy: A two-item food or beverage minimum is not required, but the venue strongly encourages each guest to purchase two items.
Tickets: Tickets are available through City Winery at https://tickets.citywinery.com/event/boston-comedy-festival-comedy-contest-preliminar-aj25p9