Upcoming Events
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
Vintage Fashion Pop-UP!
New kid on the block York & Main is hosting a Vintage Fashion Pop-up Show & Sale!
Arts on Main First Friday
Opening Reception for "THE IMPOSSIBLE JUST TAKES A LITTLE LONGER" featuring Bruce Fransom and Ed Gorham. Visit Arts on Main for more information.
York & Main: Vintage Fashion Pop-UP!
New kid on the block York & Main is hosting a Vintage Fashion Pop-up Show & Sale!
Ware Episcopal Church Farmers Market
The Gloucester Farmers Market at Historic Ware Church will take place on the second Saturday of the month, May through September, 9:00 a.m. until 1:00 p.m.
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
Mercy Creek at Gloucester Brewing Company - Live Music
Mercy Creek comes to Gloucester Brewing on May 12th for some live music!
They’ll be playing their unique brand of folk rock at GBC from 4 to 7 pm, so be sure to come by! Meanwhile, Gumbeau’s Catering will provide the food with their trucks. Can’t wait to see y’all there!
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.
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!
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.
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.
York & Main: Ask a Design Pro Interiors Event, Day 1
June's event from York & Main is focused on Interior Design!
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.
Ware Episcopal Church Farmers Market
The Gloucester Farmers Market at Historic Ware Church will take place on the second Saturday of the month, May through September, 9:00 a.m. until 1:00 p.m.
York & Main: Ask a Design Pro Interiors Event, Day 2
June's event from York & Main is focused on Interior Design!
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.
Flat Iron Crossroads Concert
THE ENGLISH CHANNEL
America's premier British Invasion band performing British pop, rock & prog hits of the mid 60's & 70's, faithfully recreated to sound just like the original recordings, just like you remember. Tickets at flatironcrossroads.com
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
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.
It's a Wrap Reception
The 2024 Heart of the River Collection will be on display at the Fine Arts Museum of Gloucester from June 9th through June 30th. Don’t miss this fun end to the events of the 2024 Gloucester Arts Festival. Reception features light hor d'oeuvres and refreshments. Free and open to the public!
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
Ware Episcopal Church Farmers Market
The Gloucester Farmers Market at Historic Ware Church will take place on the second Saturday of the month, May through September, 9:00 a.m. until 1:00 p.m.
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
Historic Garden Week: Gloucester-Mathews Tour
Gloucester tour will be on Saturday, April 20
Garden at Goshen will be on Sunday, April 21
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.
Beer Garden at the Daffodil Festival
Get ready for a day of fun and festivities at our highly anticipated Beer Garden Event, hosted by the Gloucester Main Street Association!
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.
Village Dog Spa at the Daffodil Festival
Make sure you don’t miss the Village Dog Spa booth at the Daffodil Festival!
38th Annual Daffodil Festival
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!
Daffodil Festival Sale at Goodman's Antiques
Explore the charm of the past at Goodman's Antiques, and embrace the joy of the Daffodil Festival this Saturday, April 4th! All items with a floral motif will be 20% off!
Gloucester Daffodil Show Preparation Workshop
Join the Gloucester Daffodil Club for a Daffodil Show Workshop, held at Brent & Becky's Bulbs in the Chesapeake Lounge, on Thursday, April 4th. Identify your daffodils and learn ways to stage and show them with the help of Brent Heath and GDC members.
Retailpreneur Series - Part 3
Join the Retail Alliance CEO, Jenny Crittenden along with Stephanie Heinatz, founder of Consociate Media for our three-part workshop on Retail Trends.
Biscuit, Brunch & Bubbly
Mimosa Flight & Southern Biscuit Board, 3 Housemade biscuits with accoutrements. $40 per person, limited spots available.
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.
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!
2024 Annual Business Awards
Join the Gloucester County Chamber of Commerce, Saturday, February 17th, 2024 from 6:00 p.m. - 10:00 p.m. at the Fine Arts Museum of Gloucester to honor and celebrate local businesses and business leaders!
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.
First Friday on Main Street - March
February’s First Friday is here! On February 2nd, shops will be open late on Main Street with special events at participating businesses!
Farren Winter at Gloucester Brewing Company - Live Music
Troy Breslow joins us for live music this week!He’ll be playing at GBC from 6 to 9 pm, so make sure you don’t miss it! Meanwhile, Gumbeau’s Catering will provide the meals with their food trucks!
Restaurant Week 2024
Enjoy specially crafted menus, unique cocktails, & unique specials during the week from an array of exquisite dining options!
Troy Breslow at Gloucester Brewing Company - Live Music
Troy Breslow joins us for live music this week!He’ll be playing at GBC from 6 to 9 pm, so make sure you don’t miss it! Meanwhile, Gumbeau’s Catering will provide the meals with their food trucks!
2024 Annual Business Awards hosted by the Gloucester County Chamber of Commerce
Join us Saturday, February 17th 2024 from 6:00 p.m. - 10:00 p.m. at the Fine Arts Museum of Gloucester (6894 Main Street, Gloucester, VA 23061) to honor and celebrate our local businesses and business leaders!
Mercy Creek at Gloucester Brewing Company - Live Music
Mercy Creek joins us for live music this week!He’ll be playing at GBC from 6 to 9 pm, so make sure you don’t miss it! Meanwhile, Nomads will provide the meals with their food trucks!
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!
Find Love on Main Scavenger Hunt! FREE EVENT
Can you find LOVE on Main Street? Register today for this 2024 free event Find LOVE on Main Street Scavenger Hunt presented by Gloucester Main Street Association.
February Open House and Mixed Media Demo at York & Main
Fresh vintage goods and new artworks await! Stop in and see what is new.
February Open House at York & Main
Fresh vintage goods and new artworks await!
So stop in and see what is new.
First Friday on Main Street - February
February’s First Friday is here! On February 2nd, shops will be open late on Main Street with special events at participating businesses!
Information Intoxication Trivia Night at GBC (recurring event)
Come on down for trivia at Gloucester Brewing Company every Monday night! Starts at 7pm, with a different food truck each week!
UFO CRAFTernoon at York & Main
The York & Main showroom is hosting two Crafternoons in January!
Information Intoxication Trivia Night at GBC (recurring event)
Come on down for trivia at Gloucester Brewing Company every Monday night! Starts at 7pm, with a different food truck each week!
CRAFTernoons at York & Main
The York & Main showroom is hosting two Crafternoons in January!