SPECIAL EVENTS
Gloucester Museum of History Second Floor Grand Opening
Join the Gloucester Museum of History to welcome their newly renovated second-floor exhibit!
Rick 'n Roast presented by The Fairfield Foundation
Join us for a FREE event about limerick burning, a historic method once used by brick masons to roast oyster shells for mortar. The demonstration will show how oyster shells were turned into a vital building material.
Magnolia Boulevard at Flat Iron Crossroads
Magnolia Boulevard hits the stage at Flat Iron Crossroads.
Freedom- Freedom Lost, Freedom Gained: The Pressing of Dunmore's Proclamation
Experience "Freedom – Freedom Lost, Freedom Gained: The Pressing of Dunmore’s Proclamation"—a powerful living history performance presented by Shades of Our Past and the Watermen’s Museum.
Individually Twisted at Flat Iron Crossroads
Individually Twisted hits the stage at Flat Iron Crossroads.
Christmas and Holiday Parade & Tree Lighting
Get ready for a full day of holiday cheer in Gloucester Village with the Christmas and Holiday Parade, Tree Lighting, Main Street Open House, and Festival of Trees!
Furnace Mountain Band at Flat Iron Crossroads
Furnace Mountain Band hits the stage at Flat Iron Crossroads.
Christmas at Ware
Join Gloucester Farmer’s Market for a cheerful celebration of local vendors and community spirit.
Holiday Blues-A-Palooza V at Flat Iron Crossroads
Holiday Blues-A-Palooza is coming back to Flat Iron Crossroads for a fifth season featuring Deanna Bogart, The Eric Scott Band, Jenny Langer, and Jonathan Sloane.
Gloucester Daffodil Festival
Join Gloucester’s most cherished celebration to kick-off spring! The 40th Gloucester Daffodil Festival lights up Main Street on March 28 & 29, 2026.
Gloucester Daffodil Show
Don’t forget to visit the Gloucester Daffodil Show during your visit to the 40th Gloucester Daffodil Festival!
2026 Historic Garden Week
The 2026 Historic Garden Week Tours are blooming across Virginia — and the Gloucester/Mathews Tour will take place on Saturday, April 18th!
Communion of Hearts: Adrienne el Gilbert: Historical Drama
Following on the heels of General Lafayette’s triumphant Farewell Tour (1824-1825), we find him communing, as he often did, with his dear departed wife, Adrienne. They share with us their thoughts, their reminiscences, and their love.
Do not miss this beautiful love story!
Fall Homestead Market
This fall-inspired market celebrates the warmth of simple living, with a carefully curated lineup of local artisans, handmade goods, cozy home décor, baked treats, seasonal produce, and rustic charm at every turn..
Halloween Spooktacular Driving Tour
Do you enjoy spooky decorations, ghoulish lights, and all things Halloween? Sign up your home or business to be a featured stop on Gloucester County’s Halloween Spooktacular Driving Tour this October!
Tavern Concert: Music of the Revolution
Tavern Concert: Music of the Revolution
Enjoy an afternoon of 18th and early 19th century compositions inspired by the American Revolution performed in the historic setting of our 1770 tavern ballroom
Camp Cardinal Haunted Walking Trail
Camp Cardinal DARES you to take on their 2025 Haunted Trail!
Appalachian Jam-Grass Festival at Flat Iron Crossroads
Just in time for fall, we’re stoked to throw down at the outdoor Appalachian Jam-Grass Festival with Colby T. Helms & the VA Creepers, Kitchen Sink, and Liam Purcell & Cane Mill Road. Plenty of pickin’, heartfelt tunes, and jams that’ll keep you moving all night!
Oktoberfest at Sanders
Celebrate Oktoberfest with vendors, food, music, and drinks at Sanders!
Battle of The Hook - Commemoration Ceremony
Join us on October 3, 2025, to commemorate the 244th anniversary of the Battle of the Hook.
Bill and Pam Gurley with Special Guest Bobby Hornsby at Flat Iron Crossroads
Bill, Pam, and Macon Gurley are bringing their music back to Flat Iron on Saturday, September 27th. Their Fall appearance has become a tradition that acoustic music fans look forward to.
Guinea Jubilee
Celebrating the people and traditions of the men and women who work on the water in Gloucester, presented by the Guinea Heritage Association.
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.
Gloucester Get Together - We the People: A Yorktown Battlefield Event
Gloucester County, Virginia, home of the American Revolution's second surrender, is proud to support the We the People: A Yorktown Battlefield Event- Revolutionary Festival and Ken Burns' new documentary screening.
Wine, Whiskey & Whatnot
This premier event brings together Virginia’s top wineries, delicious food vendors, unique artisans, and lively music for a day of pure enjoyment.
Winemaker Weekend: Silver Hand Meadery
Featured winemaker will stay at Camp Cardinal, giving guests plenty of opportunities to ask questions, share stories and deepen their appreciation for Virginia wine.
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.
E Pluribus Unum: Freedom Through Fashion & Fabric Pop-up Exhibition & Community Workshop
Throughout the exhibition, regional textile and fashion designers and makers will contribute their own works to the display, showcasing the rich tradition of fiber arts in our community. Stay tuned for our upcoming exhibition talk with experts and artists whose work intersects art and history—exploring how textiles have shaped identity, resistance, and cultural expression across generations.
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.
RiverJam
Arts on Main’s 9th annual RiverJam hosted by Flat Iron Crossroads playing all your favorite live music.
Winemaker Weekend: Ashton Creek Vineyard
Featured winemaker will stay at Camp Cardinal, giving guests plenty of opportunities to ask questions, share stories and deepen their appreciation for Virginia wine.
The Herbalist's Garden Presents Herbal Mocktails at Zoll Vineyards
Craft your own botanical bitters and savor delicious herbal mocktails in this hands-on workshop.
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.
From Colony to Country
Step back in time for a Revolutionary drama set in the summer of 1775. Watch as Lewis Burwell of Fairfield visits John Page at Rosewell to ponder weighty decisions.
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.
Movie on Main - Free Community Movie Night
Celebrate the end of summer with a fun-filled evening at Movie on Main!
Bring the whole family to enjoy a free community movie screening right in the heart of Main Street.
Celebrate National Honey Bee Day at Brent and Becky's Gardens
Celebrate all things Honey Bee at Brent and Becky’s!
3rd Annual Cobia Tournament
Whether your fishing for the biggest catch or supporting from the seaside, there’s something for everyone at the 3rd Annual Cobia Tournament.
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!
Open House: Bethel Baptist Church Legacy Room
Step into history and celebrate a cornerstone of Gloucester’s African American heritage at the Bethel Baptist Church & Legacy Room Open House.
Open House at Walter Reed Birthplace
Explore the tiny house that became the birthplace of Walter Reed, the army physician who studied the cause of yellow fever.
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.