Come join us for a fun-filled day at Zoll Vineyards! Get crafty and create your very own cork ornament to take home.

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.

Join us at Zoll Vineyards for their Indoor Winter Market!

Step into the warmth and charm of the season as Gloucester opens the doors to its most treasured historic sites! Join us for the Historic Holiday Open House, a festive evening filled with holiday cheer, community spirit, and a celebration of our rich heritage.

Join Gloucester Farmer’s Market for a cheerful celebration of local vendors and community spirit.

Join us for a special evening at the museum as we extend our hours for a festive holiday experience! Enjoy complimentary hot apple cider, seasonal decorations, and warm holiday cheer throughout the galleries.

Indulge in the spirits of the holidays at Zoll Vineyards.

Courthouse Community Prchestra presents free, festive holiday concerts.

Furnace Mountain Band hits the stage at Flat Iron Crossroads.

Courthouse Community Prchestra presents free, festive holiday concerts.

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!

Individually Twisted hits the stage at Flat Iron Crossroads.

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.

Magnolia Boulevard hits the stage at Flat Iron Crossroads.

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.

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!

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..

Tavern Concert: Music of the Revolution

Enjoy an afternoon of 18^th and early 19^th century compositions inspired by the American Revolution performed in the historic setting of our 1770 tavern ballroom

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!

Celebrate Oktoberfest with vendors, food, music, and drinks at Sanders!

Join us on October 3, 2025, to commemorate the 244th anniversary of the Battle of the Hook.

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.

Join the annual 5k and Fun Run at the Guinea Jubilee!

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

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.

This premier event brings together Virginia’s top wineries, delicious food vendors, unique artisans, and lively music for a day of pure enjoyment.