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Comedy Weekend

Two Nights of Gut-Busting Comedy

Feb. 20 & 21, 2026 ~ Two Shows Per Night!

Travelers and locals to the Charlottesville area looking for a laugh can join us for our annual LOL! Comedy Weekend. Welcoming professional jokers from all around, this will be a festive weekend of comedy shows in Charlottesville, VA, accompanied by a fully stocked cash bar to get everyone primed and ready for the show.

With a full two nights of gut-busting performances, Boar’s Head has a jam-packed weekend of funny business lined up.


Food, Drink & Show Times

A bar will be available at the event with drinks for purchase for guests of all ages. Light fare such as charcuterie boards, wings and cookies will be available for purchase.

Show times each night are at 6 p.m. and 9 p.m., and doors open 30 minutes prior to each show. 

If you bring a larger appetite, our 4-diamond Mill Room Restaurant is now taking dinner reservations for before and after the show.

Ticket Information

Book your tickets now because these masters of comedy are sure to fill the house quickly. There are two shows per night. The early shows recommended for an 18+ audience, and the later shows are for adults 21 or older.

VIP Tickets

Upgrade your experience with a VIP table! Each VIP table includes:

  • Tickets and a reserved table for four or eight near the stage
  • One charcuterie board for a table of four / Two charcuterie boards for a table of eight
  • Four drink tickets (valid for one beer, one glass of wine, one cocktail each) for a table of four / Eight drink tickets for a table of eight

View Ticket Info

Overnight Stay Package

Experience all that Boar's Head has to offer with a discounted overnight stay package that includes tickets for both nights of the LOL! Comedy Weekend.

View Overnight Package

Mill Room Dinner

Pair your comedy show with an elegant dinner at the legendary Mill Room Restaurant. Reservations are strongly recommended.

Mill Room Info

Matt Bergman

Emcee for Feb. 20 and 21

Matt Bergman realized his love for comedy in his last year of college where he was pursuing a degree in criminal justice. After graduating he realized he was afraid of criminals and decided stand-up comedy was the way to go. It was a wise move. Bergman is easily relatable and versatile, a skillset that has opened the door to TV appearances on Gotham Comedy Live, Comedy Central Live and a Dry Bar Comedy Special. 

His recently released album, Mostly Nice, was called “really tough to purchase” by his mother. It was released on Rhizome Records and can be heard on Sirius/XM. 

Take a Listen!

Paul Snyder

Headliner for Friday, Feb. 20

Paul Snyder is a must-see in the world of comedy, known for his unique blend of humor and relatable storytelling. A regular performer at clubs and theaters nationwide, Paul released his debut Dry Bar Comedy special, “I Left the House for This”, in August 2024. The special’s first clip has already garnered over 2 million views on YouTube. His comedy offers a mix of personal anecdotes and observational humor that resonates with audiences of all ages. With a laid-back delivery and a knack for making even the smallest crowds feel like old friends, Paul’s performances are consistently warm, engaging, and entertaining

Watch A Clip

Robert Mac

Headliner for Saturday, Feb. 21

Robert Mac is an award-winning comedian (Comedy Central’s national stand-up competition) a non-award-winning Master of Ceremonies, and a fake motivational speaker, among other things. His act is clever, clean, and ideal for audiences wanting something a little more cerebral. It’s brainy and deadpan instead of brain-dead and pandering.

Watch A Clip

Matt Conn

Opening Act for Saturday, Feb. 21

Matt Conn has performed all over the country including the World Famous Hollywood Comedy Store, Funny Business Shows, LaughFest, Brew HA-HA, Traverse City Comedy Festival and Mark Ridley’s Comedy Castle where he was a finalist in the Detroit to L.A. competition.

He’s been described as having a whimsical balance of witty observations combined with boyish charm. Matt’s clean and clever humor strikes a chord with audiences of all ages

View Matt's Clips