SPECIAL EVENTS
Fireside Collective at Flat Iron Crossroads
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.
Concerts on the Green: Clan MacCool Band
Free concert at Gloucester’s Historic Courthouse Circle! Clan MacCool Band washes ashore for a pirate-themed scallywag shindig.
RiverJam
Arts on Main’s 9th annual RiverJam hosted by Flat Iron Crossroads playing all your favorite live music.
Concerts on the Green: Ami Baker
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.
Concerts on the Green: Just Dan
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.
Concerts on the Green Series Finale: Courthouse Community Orchestra and friends
Free concert at Gloucester’s Historic Courthouse Circle! The Courthouse Community Orchestra will provide an enchanting afternoon of tunes.
Carolina Beach Music at Flat Iron Crossroads
Gary Lowder & SMOKIN’ HOT are bringing their award-winning blend of R&B, soul, and Carolina beach music to the Flat Iron stage!
Concerts on the Green: DJ Big-E Diceman
Free concert at Gloucester’s Historic Courthouse Circle! DJ Big-E Diceman spinning your favorite pop, rap, and hip-hop classics.
Jerry Fest: The Days Between at Flat Iron Crossroads
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!
Good Shot Judy at Flat Iron Crossroads
The Mid-Atlantic’s No. 1 high octane swing band, Good Shot Judy is performing in Gloucester, VA at Flat Iron Crossroads!
Concerts on the Green: Nathan Stephenson
Free concert at Gloucester’s Historic Courthouse Circle! Tom Euler belts out blues and rock with covers and originals.
The Deloreans at Flat Iron Crossroads
The Ultimate 80s Tribute band is back again! Gear up for The Deloreans on Saturday, July 19th, 2025.
Willie Williams Band at Flat Iron Crossroads
Roots Rock, Southern Americana, and Country Soul artist, Willie Williams, is bringing the band to Flat Iron Crossroads!
Concerts on the Green: Toby and Larry
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!
Anthony Rosano and the Conqueroos at Flat Iron Crossroads
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!
Concerts on the Green: Tom Euler - Cancelled
Free concert at Gloucester’s Historic Courthouse Circle! Tom Euler belts out blues and rock with covers and originals.
Gloucester's Play All Day
Join Gloucester’s Play All Day with live music, food truck, and free sunset yoga.
Lord Nelson Band at Flat Iron Crossroads
Flat Iron Crossroads hosts Lord Nelson Band, an original rock and roll set from the foothills of Virginia’s Blue Ridge Mountains.
Freedom Junction at Flat Iron Crossroads
Join us in o hear Nashville’s funk-rock jam band, Freedom Junction.
Pressing Strings
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 at Flat Iron Crossroads
The Bobby Thompson Trio performs originals, blues, rock, and related styles and is based in Washington D.C.
Live Music by Bubba Ward - YROC
Join us for live music on the deck with Bubba Ward! Check him out on Facebook.
The 2024 Guinea Jubilee
Save The Date!
The Guinea Heritage Association’s mission is to preserve the history and values of the unique community called Guinea.
2024 Gloucester Wine Festival
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.
Ami Baker- Concerts On The Green
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.
Good Shot Judy- Flat Iron Crossroads
THE SWING AND THE SWAGGER…
It’s hard to nail an exact moment when Good Shot Judy came to life.
Just Dan - Concerts On The Green
We are excited to welcome Just Dan back to the court circle for another year!
Village Arts Day
Village Arts Day includes an Artisan Market, Live Performances, Music, and More!
Clan MacCool Band- Concerts On The Green
We be so excited t' ahoy the Clan MacCool Band back t' the Historic Courthouse Circle fer another year!
Bobby Blackhat Band- Flat Iron Crossroads
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!
Toby & Larry- Concerts On The Green
We are so excited to welcome Toby & Larry back to the court circle!
Isaac Hadden Organ Trio- Flat Iron Crossroads
Isaac Hadden Organ Trio is a heavy-hitting, improvisational, cosmic groove ensemble, carving out a distinct voice in the world of funk, jazz, rock, and R&B.
Bourbon, Bacon & Beer Fest
Indulge in the perfect trio of flavor at our Bourbon, Bacon & Beer Fest! Unlimited craft beer, 10 Bourbon tastings & 1/2 lb Bacon!
Alice in Wonderland Weekend at Camp Cardinal
Fall down the rabbit hole and into a whimsical world of wonder during our Alice in Wonderland Weekend at Camp Cardinal!
POSTPONED DUE TO WEATHER: Courthouse Community Orchestra- Concerts On The Green
Join us on Wednesday June 5th for a lovely performance by the Courthouse Community Orchestra.
Symphony Under The Stars
Celebrating its 18th year making music accessible to everyone! We welcome you to join us for the Symphony Under the Stars FREE Family Concert.
The June 1st concert by the Virginia Symphony Orchestra is touted as one of the most anticipated events of the year in the community, drawing well over a thousand families and community members to Main Street for an evening of great food and music.
Dive into what the locals love.
View all the local programs and events cherished by the Gloucester community, welcoming friends from near and far with open arms.