Wednesday, June 19, 2024

Brews and Tunes: Live Music Around the Historic Triangle this Weekend

Matt Chambers runs the local entertainment business Squared Away Entertainment, which provides entertainment services such as Doing and trivia nights. (Courtesy of Matt Chambers)

HISTORIC TRIANGLE — Each week, WYDaily features a local musician, comic, group, event, or venue as part of its Brews and Tunes! This week, Ben Mackin chats with local DJ and trivia night host Matt Chambers.

If you have gone to a trivia night hosted by a bar or brewery in Williamsburg in the last few years, chances are good that it was one hosted by Matt Chambers.

Several nights a week Matt is either hosting a trivia night or spinning tunes at a wedding or event through his entertainment business, Squared Away Entertainment.

Here are some quick facts about Matt.

Q: What is your ideal crowd to DJ for?

A: I really like DJ the crowds that college age to young professionals my age, 35 and under. Mainly because I grew up around the same time and I know what will get them going. But I can do any crowd. I like playing for older people too. I like throw out stuff that I love that people have not heard in ten or fifteen years.

Q: When was your first gig as a DJ and how did it go?

A: The first time I ever DJed. I was at a friend’s bar in Richmond. I did a good job DJing, but I couldn’t tell you what I played. I was in such a whirlwind trying to learn everything. I was learning how to read the crowd, I played stuff the way you hear it on the radio. No blending, no mixing. I built on that and learned how to mix songs and genres. Now I can go from a 70s banger to a 2000s banger so that everyone is having a great time.

Q: How long have you been hosting trivia nights?

A: It will be five years this year. I tried it out because it was different. I tried DJing in the Williamsburg and that wasn’t getting anywhere. I tried karaoke. That did ok, but I didn’t like doing karaoke at all. I found speed quizzing and Luci Legaspi and Robby Willey gave me my first shot do it at Virginia Beer Company (VBC). They really liked it there. Then it grew from VBC to Green Leafe and now I am booked five nights week.

Q: Where and when do you host speed quizzing?


Monday- Green Leafe, 765 Scotland St., 7:30 p.m.

Tuesday- Alewerks Brewing Company, 189B Ewell Rd., 7 p.m.

Wednesday- Precarious Beer Project, 110 S. Henry St., 6:30 p.m.

Thursday- Virginia Beer Company, 401 Second St., 6:30 p.m.

Friday- Billsburg Brewery, 2054 Jamestown Rd., 7 p.m.

For more information on Matt Chambers and Squared Away Entertainment, check out his Facebook page or go the Squared Away Entertainment website.

Ready to head out for the weekend? Check out who is playing where around the Historic Triangle!

Want to be included in WYDaily’s weekly Brews and Tunes column? Send Ben Mackin an email at!

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