Upcoming Events

Flat Iron Crossroads Concert
Apr
27

Flat Iron Crossroads Concert

ANTHONY ROSANO AND THE CONQUEROOS

Singer, guitarist, songwriter, and bandleader, Anthony Rosano, has always been drawn to grit, gravitas and the connection that comes from making music. Although his music roots are implanted in the firmament of the blues, he takes his cue from any number of archival influences. Tickets at flatironcrossroads.com

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Flat Iron Crossroads Concert
May
11

Flat Iron Crossroads Concert

COLBY HELMS & THE VIRGINIA CREEPERS

At the bottom of the Southwest Virginia foothills half-a-mile from the nearest neighbor, 21-year-old Colby T. Helms resides in an “underground house” built by his late father on land his family has owned for generations. Colby first dreamed of making music his life at age 12, when a group of Blue Ridge Mountain old-time and bluegrass players performed songs like The Ozark Mountain Daredevils’ “Standing On The Rock” and the gospel classic “A Beautiful Life” at his father’s funeral in Boones Mill, VA. To make his dream a reality, he taught himself guitar, banjo, and mandolin by watching local performers and YouTube videos Tickets at flatironcrossroads.com

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River Jam
May
18

River Jam

This annual music festival and fundraiser for Arts on Main features local artists, musicians, and food and drink for an afternoon of fun with a view of the water. Visit Arts on Main for more information.

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Gloucester Arts Festival
May
31
to Jun 29

Gloucester Arts Festival

The Eighth Edition of the Gloucester Arts Festival kicks off on May 31, 2024! From the new Fine Arts Museum of Gloucester to the premier Plein Air Invitational of the Middle Peninsula, this month-long cultural event is bigger and better than ever. For more details on individual events that are being held during the month of June please click the button below!

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Paint Main 2024
Jun
1

Paint Main 2024

On Saturday, June 1st, the 2024 Gloucester Arts Festival Plein Air festival painters will compete in a fast-paced paint-out along Main Street from ten a.m. till noon. 

Community painters also are welcome to register for this Paint Main event and compete for separate prizes. Judging will follow on the Tabb House Lawn. For more info, click on the button below.

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Symphony Under the Stars
Jun
1

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. To learn more, click the button below.

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Local Color Show
Jun
7

Local Color Show

Arts on Main’s June show and First Friday reception shines a spotlight on the beauty and talent of the Middle Peninsula. The event features captivating images of local scenes or impressive art pieces created by talented local artists. This showcase is part of the Gloucester Arts Festival’s month-long series of events. For more information and events please visit the gloucesterartsfestival.com website.

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Plein Air Gala
Jun
8

Plein Air Gala

The Met Gala in our own backyard! Join the Gloucester Arts Festival as the culmination of the week long Plein Air Competition ends with a spectacular gala at the Fine Arts Museum of Gloucester!

Put on your finest attire and walk up our red-carpeted steps while enjoying a glass of prosecco to view the Heart of the River Collection. Tickets available here.

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Flat Iron Crossroads Concert
Jun
15

Flat Iron Crossroads Concert

ISAAC HADDEN ORGAN TRIO

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. The group performs intricate yet accessible original music and fresh arrangements of classic tunes. Tickets at flatironcrossroads.com

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Village Arts Day
Jun
29

Village Arts Day

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

A free, family-friendly day celebrating the Arts and Artists from Gloucester and around the region! To find out more click the button below.

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Flat Iron Crossroads Concert
Jul
6

Flat Iron Crossroads Concert

THE BONESHAKERS

No holds barred funk, blues, and rock that marries the sounds and spirits of Detroit Rock City, Memphis, and Mussel Shoals. In the remarkable 25-year career of The Boneshakers, the iconic band has always been led by world-renowned guitarist Randy Jacobs of Was (Not Was). The band and members have toured and recorded with Bonnie Raitt, BB King, Keb Mo, Aretha Franklin, Elton John, Bootsy Collins, Tears 4 Fears, Bob Dylan, Stevie Wonder, Gov’t Mule, and Iggy Pop…just to name a few. Tickets at flatironcrossroads.com

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Flat Iron Crossroads Concert
Apr
20

Flat Iron Crossroads Concert

Runnin’ Shine

Hot country act with its members hailing from Virginia by way of Alabama, New York, and New Hampshire. Playing together since February of 2015, Runnin’ Shine is a tight, four-piece comprised of Janice Chandler on vocals and acoustic guitar, Richie Bohr on lead electric guitar, Bill Snow on drums, and Jim Cahoon on the bass. Brought together by really good luck and a few mutual friends, each player gives a unique energy and experience to the band. Tickets at flatironcrossroads.com

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Flat Iron Crossroads Concert
Apr
13

Flat Iron Crossroads Concert

REID HARRISON TRIBUTE WITH THE DIMESLOTS

This show is a celebration of life for our cherished friend and volunteer, Reid Harrison. He was instrumental in the early stages of inception with sound and production, booking talented artists, developing our website. Featuring The Dimeslots.

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Gloucester Daffodil Show
Apr
6

Gloucester Daffodil Show

Spring is on its way, and the flowers are beginning to bloom—that means the Daffodil Festival is almost here!

The Gloucester Daffodil Show is a two day event. Saturday, April 6 from 2-5 (awards start around 2:15) and Sunday, April 7 from 12-5.

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38th Annual Daffodil Festival
Apr
6
to Apr 7

38th Annual Daffodil Festival

  • 6509 Main Street Gloucester, VA, 23061 United States (map)
  • Google Calendar ICS

The Daffodil Festival will celebrate its 38th year on April 6th & 7th in Gloucester, the Daffodil Capital of America! Live music, dazzling displays, and more!

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Rosewell Reopens for Spring
Mar
29

Rosewell Reopens for Spring

The Fairfield Foundation will reopen the Rosewell Ruins and Visitor Center for the 2024 season on Friday and Saturday, March 29 and 30, from 10 am to 4 pm. Following closure on Easter Sunday, the historic site will open on Fridays and Saturdays from 10 am to 4 pm and on Sundays from 12 pm to 4 pm through October.

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Willie Williams Trio at Flat Iron Crossroads
Mar
23

Willie Williams Trio at Flat Iron Crossroads

The Travis Colby Band has curated a special New Orleans style Mardi Gras show for Flat Iron Crossroads and will be covering iconic artists such as the Meters, Professor Longhair, Dr. John, and many others. The ensemble will groove with piano, drums, saxophone, and trumpet, delivering that authentic NOLA sound for you to dance to all night long! PLUS, catering this event is T-Boyeés Couillon Bon who specializes in Creole/Cajun cuisine and seasoning. Bring your beads, dancing shoes, appetite, and let’s have a blast!

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Piha Aloha at the Gloucester Brewing Company
Mar
9

Piha Aloha at the Gloucester Brewing Company

Come out to GBC to be part of Piha Aloha's Gloucester debut! They will be here all day serving their delicious menu, including traditional Hawaiian BBQ, as well as island favorites.

Not only will they have great food, but amazing music as well! Join us starting at 5pm to catch their band play beautiful, traditional music.

Great food, and great music go really well with our beer! So come sit back, relax, and pretend you're on Island Time.

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Mardi Gras Party with The Travis Colby Band at Flat Iron Crossroads
Feb
10

Mardi Gras Party with The Travis Colby Band at Flat Iron Crossroads

The Travis Colby Band has curated a special New Orleans style Mardi Gras show for Flat Iron Crossroads and will be covering iconic artists such as the Meters, Professor Longhair, Dr. John, and many others. The ensemble will groove with piano, drums, saxophone, and trumpet, delivering that authentic NOLA sound for you to dance to all night long! PLUS, catering this event is T-Boyeés Couillon Bon who specializes in Creole/Cajun cuisine and seasoning. Bring your beads, dancing shoes, appetite, and let’s have a blast!

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