Boston Comedy Festival Comedy Contest Preliminary Round 5
Boston Comedy Festival Comedy Contest Preliminary Round 5 brings 12 comedians to City Winery Boston as part of a national stand-up competition featuring 96 performers over eight preliminary rounds. Contestants are competing for 32 semifinal places and a share of $7,000 in prize money, giving audiences a chance to discover comedians before they become widely known.
The evening is hosted by Boston comedy veteran Steve Bjork and features nationally touring comedian Orlando Baxter as the special guest headliner. Baxter has appeared on *Conan*, Comedy Central, and BET, performed at major comedy festivals, and toured with the Bored Teachers Comedy Tour. His material draws on his experiences as a former high school teacher, as well as stories about family and everyday life.
When: November 12, 2026
Showtime: 7:00 PM. Doors open at 6:00 PM.
Venue: Haymarket Lounge at City Winery Boston, 80 Beverly Street, Boston, MA 02114
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 also lists tickets starting at $30.
Contest: Twelve comedians compete for one of 32 spots in the semifinals. The larger competition includes 96 comedians from across the United States and occasionally Canada, divided among eight preliminary rounds.
Host: Steve Bjork, a longtime Boston comedy performer who has also appeared at comedy clubs, casinos, and theaters around the country.
Special guest headliner: Orlando Baxter, a nationally touring comedian and former high school teacher known for appearances on *Conan*, Comedy Central, and BET, as well as the Bored Teachers Comedy Tour.
Dining: Food and beverages can be ordered at the table during the show. Guests may also arrive early for a meal in City Winery’s restaurant; reservations are encouraged through Resy beginning one month before the show.
Venue note: City Winery strongly encourages each guest to purchase two food or beverage items, although a two-item minimum is not required.