Squared Away Entertainment

Squared Away Entertainment Squared Away Entertainment provides DJ/MC services, interactive Speedquizzing trivia, and modern photo booth rentals across Virginia and beyond.

Whether it's a wedding, corporate event, school function, or private party—I’ll get your event squared away.

Excited to be a part of Lead Greater Williamsburg!
05/26/2026

Excited to be a part of Lead Greater Williamsburg!

LEAD Greater Williamsburg is proud to announce the members of its Class of 2027, 27 professionals representing a diverse cross-section of organizations and industries throughout the City of Williamsburg, James City County and York County.

Sponsored by the Greater Williamsburg Chamber of Commerce, LEAD Greater Williamsburg is a community immersion program that provides opportunities for recognized and emergent leaders to collaborate on issues of importance to the region. Over the course of an intensive nine-month program, class members participate in educational sessions, tours, and candid conversations with community leaders, gaining a deeper appreciation for their region.
Class members explore education, public safety, health and human services, economic development, environmental sustainability, local and state government, workforce development, and the military.

Since its founding in 1992, the program has graduated more than 400 diverse and accomplished individuals. Alumni go on to serve as elected officials, local government planning commissioners, and non-profit board members, building lasting personal relationships and an invaluable professional network along the way.
The Class of 2027 members and their organizations are:
Alejandra Ramello, Visit Williamsburg
Alice Jacobs, Merrill Lynch
Andrea Case, James City County (JCC)
Brett Smith, Whitley's Peanut
Charles Gates, WJCC Community Action Agency
Crystal Bright, Dominion Energy
Donita Snook, Synergy Home Care
Grayson Moore, Liz Moore Real Estate
Jenny Barthlome, Riverside Health System
John Becker, Williamsburg Landing
Judson Crihfield, Child Development Resources (CDR)
Katie Meis, York County
Maggie Harbick, Chesapeake Bank
Matt Chambers, Squared Away Entertainment
Matthew Pollino, Grove Outreach
Megan Whaley, Premier Home Appraisals
Melinda Mdluli, Heart Ministry
Melissa Jeffries, Chesapeake Bank
Mike Loy, Busch Gardens
Nathaniel Rock, Williamsburg Area Transit Authority (WATA)
Nicholas Kier, WJCC Public Schools
Odalis Delgado, James City County (JCC)
Patty Hartigan, Colonial Behavioral Health
Rich Smith, Guernsey Tingle
Tabor Chapman, Williamsburg Regional Library (WRL)
Tracey Wright, Virginia Peninsula Community College (VPCC)
Zach Kirkpatrick, Junk Luggers

“We are thrilled to welcome this outstanding group of professionals to the LEAD family,” said Julie O’Neil, LEAD Board Chair. “This class represents a diverse mix of leaders from across our community, each bringing valuable experience, perspective, and a shared commitment to Greater Williamsburg. We look forward to a year of connection, learning, and collaboration that will strengthen their leadership and create lasting impact across our region.”
The Class of 2027 will begin its journey this fall, working together through monthly day-long sessions to explore the region's most pressing challenges and opportunities. Graduates will join a growing alumni network that continues to shape the future of the Greater Williamsburg community. Greater Williamsburg Chamber of Commerce

Looking for entertainment that keeps your guests engaged and your event stress-free?Squared Away Entertainment offers:🎧 ...
05/11/2026

Looking for entertainment that keeps your guests engaged and your event stress-free?

Squared Away Entertainment offers:
🎧 DJ & MC Services
🧠 SpeedQuizzing Trivia Nights
📸 Photo Booth Experiences

From weddings and corporate events to school functions, fundraisers, and private parties — we bring the energy, professionalism, and fun.

✔️ Experienced local entertainer
✔️ Fully customized experiences
✔️ Serving Williamsburg, Hampton Roads & beyond

📩 Message today to check availability for your event.

Part 2
04/30/2026

Part 2

Thank you for coming to Strictly Business Spring 2026 and stopping by my Photo Booth! Tag your friends if you see them!
04/30/2026

Thank you for coming to Strictly Business Spring 2026 and stopping by my Photo Booth! Tag your friends if you see them!

04/27/2026
Highlights from Heritage Humane Society’s Black Ties & Tails Gala at DoubleTree by Hilton Hotel Williamsburg from Saturd...
04/23/2026

Highlights from Heritage Humane Society’s Black Ties & Tails Gala at DoubleTree by Hilton Hotel Williamsburg from Saturday! Thank you all for stopping by my photobooth!

Tag your friends if you see them!

✌🏾❤️

Thanks to everyone who stopped by the Photo Booth during Field Dayz 2025!Your photos are ready! Tag your crew if you see...
10/27/2025

Thanks to everyone who stopped by the Photo Booth during Field Dayz 2025!

Your photos are ready! Tag your crew if you see then! Tap the link below to browse, download, and share your favorites:

View the full gallery: squaredawayent.zenfoliosite.com/field-day-2025-102525

Thank you to Precarious Beer Project and all the vendors for putting together a fun event!

10/21/2025

Thank you to Toano Middle School for letting me bring the beats during Friday’s lunch!

Need a DJ for your next school event? Let’s make it happen.

Address

Williamsburg, VA
23185

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