Free concert at Gloucester’s Historic Courthouse Circle! The Courthouse Community Orchestra will provide an enchanting afternoon of tunes.

Free concert at Gloucester’s Historic Courthouse Circle! Just Dan embodies the spirit of Frank Sinatra and other classics through his wide range of vocals.

Free concert at Gloucester’s Historic Courthouse Circle! Ami Baker showcases her mesmerizing guitar skills with covers and originals from a diverse array of genres.

Arts on Main’s 9th annual RiverJam hosted by Flat Iron Crossroads playing all your favorite live music.

Free concert at Gloucester’s Historic Courthouse Circle! Clan MacCool Band washes ashore for a pirate-themed scallywag shindig.

Fireside Collective has drawn on folk, blues, funk and a wide variety of bluegrass sounds to create a distinctive body of work that’s all their own.

Gary Lowder & SMOKIN’ HOT are bringing their award-winning blend of R&B, soul, and Carolina beach music to the Flat Iron stage!

Free concert at Gloucester’s Historic Courthouse Circle! DJ Big-E Diceman spinning your favorite pop, rap, and hip-hop classics.

Join us as we honor the legacy of Jerry Garcia and the music he helped bring to life with Kooler Heads, Stellar Rose, and WOLPH!

The Mid-Atlantic’s No. 1 high octane swing band, Good Shot Judy is performing in Gloucester, VA at Flat Iron Crossroads!

Free concert at Gloucester’s Historic Courthouse Circle! Tom Euler belts out blues and rock with covers and originals.

The Ultimate 80s Tribute band is back again! Gear up for The Deloreans on Saturday, July 19th, 2025.

Roots Rock, Southern Americana, and Country Soul artist, Willie Williams, is bringing the band to Flat Iron Crossroads!

Free concert at Gloucester’s Historic Courthouse Circle! Toby and Larry will be setting the summer stage with your classic peaceful beach vibes. Location Change: Museum of History back lawn!

Join us in Gloucester, VA on 6/28 to hear Anthony Rosano and the Conqueroos mix traditional Blues and Roots elements with a modern Rock delivery featuring Ron Holloway, saxophone extraordinaire!

Free concert at Gloucester’s Historic Courthouse Circle! Tom Euler belts out blues and rock with covers and originals.

Join Gloucester’s Play All Day with live music, food truck, and free sunset yoga.

Flat Iron Crossroads hosts Lord Nelson Band, an original rock and roll set from the foothills of Virginia’s Blue Ridge Mountains.

Join us in o hear Nashville’s funk-rock jam band, Freedom Junction.

Returning to Flat Iron Crossroads is Pressing Strings, a four-piece band based out of Annapolis, Maryland performing a blend of indie, soul rock, and Americana roots.

The Bobby Thompson Trio performs originals, blues, rock, and related styles and is based in Washington D.C.

Join us for live music on the deck with Bubba Ward! Check him out on Facebook.

Featuring top Virginia Wineries, live music, fine foods, art and retail vendors.There will also be Wine Tasting and Educational Seminars. Parking will be at Ware Academy with convenient shuttles.

We welcome Ami Baker to the court circle for the first time this coming July! A solo female singer-songwriter / guitarist that plays an eclectic multi-genre variety of covers & sometimes originals ranging across generations.

THE SWING AND THE SWAGGER…

It’s hard to nail an exact moment when Good Shot Judy came to life.

We are excited to welcome Just Dan back to the court circle for another year!

Village Arts Day includes an Artisan Market, Live Performances, Music, and More!

We be so excited t' ahoy the Clan MacCool Band back t' the Historic Courthouse Circle fer another year!

Flat Iron Crossroads and the Cook Foundation’s Gloucester Arts Festival are pleased to announce Bobby BlackHat Band performing on June 22nd at Flat Iron Crossroads!