2019 Comedy Weekend | Kingsmill Resort, Williamsburg VA 2019 Comedy Weekend | Kingsmill Resort, Williamsburg VA
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2019 Comedy Weekend

January 25-27, 2019

2019 Comedy Weekend

Available 01/25/19–01/27/19

Available 01/12/18–11/30/18

Combat winter’s chill this January with body-warming, gut-busting laughs throughout Kingsmill’s Comedy Weekend. On Friday and Saturday night, a lineup of some of the nation’s funniest comics will perform live to keep you hilariously entertained and rolling in the aisles. Don’t miss out on all the LOLs and ROTFLs delivered during these two  shows. Space fills up quickly, so book today!

Shows run from 8:00 - 10:15 PM each night, with doors opening at 7:00 PM. Tables may be reserved and full bar will be available.

Two-Night Package includes:

  • Friday and Saturday night accommodations in a resort guest room
  • Tickets to attend the Comedy Show both nights
  • Full breakfast daily at Elements 1010
  • Complimentary use of indoor pool and Fitness Center
  • Complimentary parking and Wi-Fi

Package starting at $127 per person, per night based on double occupancy. Two night minimum required. Package not available with other discounts or promotions, or for groups. 21-day cancellation required.

Reserve Your Stay


Individual Tickets Now Available

  • Premium Tickets - $45 per person, per day, plus tax.
  • General Seating - $42 per person, per day, plus tax.

To purchase tickets individually, call 757.258.1630.

Space is filling up quickly - call today!


Comedy Weekend Buffet

Enjoy a delicious meal with our Comedy Weekend themed buffet before the show at Elements 1010. Not included in individual tickets or Two-Night Packages.


Comedy Line Up

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2019 Comedy Weekend

Available 01/25/19–01/27/19

2019 Comedy Weekend Talent

Master of Ceremonies

Jim FlanniganJIM FLANNIGAN

Over the past few years, Jim Flannigan has become a mainstay at the top comedy clubs around the country. Hailing from Chicago, Jim's quick wit and smart humor have made him a favorite at colleges, comedy clubs and corporate events alike. Jim has spent the last few years opening for many of the biggest names in comedy, as well as recently making his TV debut on WGN. As of late, Flannigan has been gaining industry recognition, in 2016 appearing at two of the nation’s most respected comedy festivals, Gilda’s LaughFest and The Great American Comedy Festival.

Watch a Clip of Jim

Friday Night Lineup

McCaffreyKEVIN MCCAFFREY

After making his network TV debut on The Late Show with David Letterman, Kevin McCaffrey was chosen by Letterman to be the show’s warm-up comic. He is a current regular and 2-time champion of truTV’s Comedy Knockout, and appears every week on truTV’s Greatest Ever series, and truTV Presents: World’s Dumbest.

Kevin is the host of the popular College Stories podcast, a weekly show where comics, writers, and actors tell their craziest, funniest stories from college. He also hosts Away Games: A Chicago Cubs Podcast.

His previous TV appearances include VH1’s I Love the 2000s, History’s I Love the 1880s, and multiple shows on The WWE Network, including The Edge & Christian Show, and WWE’s The List. He is the lead writer for the trivia game, HQ Sports.

Watch a Clip of Kevin
Erin FoleyERIN FOLEY

Erin Foley's razor-sharp observational comedy has gotten her big laughs on @midnight, Conan, Chelsea Lately, Comedy Central, Carson Daly, Arsenio Hall, Montreal Just for Laughs, amongst a slew of others! Foley continues to crush audiences nationwide with her hysterical view on life, spot- on humor, rapid firespeech and aerbic wit like no other!

When she's not performing stand-up, Foley is also a talented actress whose credits include Curb Your Enthusiasm, NBC's Go On and the film Almost Famous. Erin has branded a unique position for herself in the industry as not only a gifted stand-up but a talented actress. Her versatility makes her one of the most incredible and admired comedians touring the country today. No surprise, The Huffington Post named her in the Top 20 in its list of "53 of our favorite comedians." Huffington Post writes, “She offers smart comedy on politics, culture, sports and commercialism that can appeal to anyone in an urban area or with a college degree."

Watch a Clip of Erin
David CroweDAVID CROWE

Some of the highlights from David Crowe’s career include his own one-hour comedy special on Showtime titled “Crooked Finger,” appearances on Comedy Central’s “Live at Gotham,” “The Bob and Tom All-Stars Comedy Hour” and the “HA! Festival” for the CBC in Canada.

David’s career launched quicker than most when, just three years after his first open mic, he won both the Seattle and San Francisco International Comedy Competitions. He has gone on to be featured at the Edinburgh Fringe Festival, The Aspen Comedy Festival, Gilda’s Laugh Fest, Halifax Comedy Festival and the Vancouver Comedy Festival just to name a few. He has also released four comedy albums: Potshot’s at Goliath, Spoken Nerd, Cruciflex and Crooked Finger, all of which can be heard on SiriusXM Satellite Radio.

He was recently hired to perform a 38 city theater tour across Canada for Investors Group Financial Services. He has also performed the likes of President Clinton, Microsoft, Boeing, Frito-Lay, Target, Ford, BP, BluRay, Starbucks, the United States Armed Forces as well as a host of other associations and groups in both the private and public sector.

Watch a Clip of David

Saturday Night Lineup

Mark ChalifouxMARK CHALIFOUX

Recognized as a “hilarious up-and-comer” by College Humor, Mark Chalifoux has been featured on Fox and IFC as well as on the “Bob and Tom” national radio show. His Midwestern upbringing contributes to the laid-back, relatable style that belies a sharp-wit and unflinching honesty honed through his rise in the comedy clubs of New York City. He’s been featured in the Boston Comedy Festival, the Limestone Comedy Festival and the Laughing Skull Comedy Festival (among others). His jokes have been heard on SiriusXM and read in Reader’s Digest (a magazine for the elderly) and he’s written for ESPN and CBS Digital.

Watch a Clip of Mark
Ryan ConnerRYAN CONNER

Originally from Washington DC, Ryan Conner was a Top-10 finalist on the most recent season of NBC's Last Comic Standing, where judge Norm MacDonald called his first set "The best 3.5 minutes I've seen in five years." In addition to touring the country doing stand-up, Ryan is a writer/producer for MTV's Ridiculousness, and was a contributing writer for two seasons of TruTV's "Billy On The Street." You can hear his album "Live From An Old Prison" anywhere albums can be heard.

Watch a Clip of Ryan
Andy HendricksonANDY HENDRICKSON

Andy Hendrickson is a comedian, writer and actor that built his career in New York City and now resides in Los Angeles. He has a clever, conversational style and has been engaging audiences for well over a decade. Since 2013, he’s had multiple TV appearances including: The Late Show with David Letterman, The Late Late Show with Craig Ferguson, and Gotham Comedy Live. In LA you can catch Andy at The Comedy and Magic Club and in New York City, Andy appears regularly at the most popular venues including the world famous Comedy Cellar. Internationally, Andy has performed at clubs and festivals throughout the world, including Canada, England, Holland and Ireland. In 2011 he performed for our troops on Outback’s Feeding Freedom Tour that provided entertainment for the troops on military bases across Afghanistan. His 3rd comedy CD “Underachiever” recently released to rave reviews and debuted in the iTunes Top 40.

Watch a Clip of Andy