SPECIAL EVENTS
Concerts On The Green : Clan McCool Band
Concerts on the Green Summer Series is back! Join us for free live music in the historic Court Circle on Main Street on select dates this summer.
Annual Luau at Gloucester Brewing Company
Celebrate the start of summer with Gloucester Brewing Company’s biggest event of the year.
Purely Natural Pop-Up at Brent and Becky's Bulbs
Favorite local vendors and bath salt workshop at famous Brent and Becky’s Bulbs
SOLD OUT Abingdon Ruritan Club Seafood Festival
Gloucester’s biggest all-inclusive seafood festival! Join this bi-annual sell out event!
Marine Science Day by VIMS
One day the year only, join VIMS for exhibits, tours, activities, and food!
Brews, Brine & Wine by Gloucester Arts Festival
Celebrating 10 years of the Gloucester Art’s Festival!
Paint Main by Gloucester Arts Festiavl
Celebrating 10 years of the Gloucester Arts Festival.
Concerts On The Green : Mike Reed Music
Concerts on the Green Summer Series is back! Join us for free live music in the historic Court Circle on Main Street on select dates this summer.
Gloucester Farmers Market at Historic Ware Church
Gloucester’s best pop-up market, every 2nd Saturday May through September.
Gloucester Farmers Market at Historic Ware Church
Gloucester’s best pop-up market, every 2nd Saturday May through September.
Concerts On The Green : Toby and Larry
Concerts on the Green Summer Series is back! Join us for free live music in the historic Court Circle on Main Street on select dates this summer.
Food Truck Frenzy
Fresh flavors, coastal vibes, family fun, music, and summer memories.
Gloucester Farmers Market at Historic Ware Church
Gloucester’s best pop-up market, every 2nd Saturday May through September.
Gloucester Farmers Market at Historic Ware Church
Gloucester’s best pop-up market, every 2nd Saturday May through September.
Gloucester Wine Festival
One of Gloucester’s favorite fall traditions- the annual Wine Festival!
Gloucester Farmers Market at Historic Ware Church
Gloucester’s best pop-up market, every 2nd Saturday May through September.
Florencia & the Feeling at Flat Iron Crossroads
Blending upbeat funky rhythms, heartfelt songwriting, soaring four-part harmonies, and a touch of jazz and Latin flair
Pressing Strings at Flat Iron Crossroads
Blend of blues, rock, and folk, wrapped in soul-stirring storytelling and toe tapping grooves.
Persophone's Return: Dinner and Gala at Zoll Vineyards
Theatrical dinner with award winning wines.
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!
Machicomoco's Earth Day Celebration
Education, activities, and food vendors at picturesque Machicomoco State Park.
Symphony Under the Starts by Gloucester Arts Festival
Celebrating two decades of free music and 10 years of the Gloucester Arts Festival.
Secondhand Saturdays
Celebrating Gloucester’s most charming thrift, antique, and boutique retail through a lens of sustainability.
Gloucester Daffodil Show
Don’t forget to visit the Gloucester Daffodil Show during your visit to the 40th Gloucester Daffodil Festival!
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.
Green Leaf Society at Flat Iron Crossroads
Join Flat Iron Crossroads for their St. Patrick’s Day Celebration with Green Leaf Society.
Carter Minor Blues Band at Flat Iron Crossroads
Join Flat Iron Crossroads for the Carter Minor Blues Band!
Timberneck Tea
Join the Fairfield Foundation for their 4th annual Timberneck Tea at beautiful Machicomoco State Park.
Working Waterfronts Photography Exhibition Opening Reception
Each photograph reflects not just a moment in time, but a deeper narrative about livelihood, legacy and the quiet strength required to survive — and thrive — where land meets water.
Tin Can Fish Band at Flat Iron Crossroads
Enjoy folk, rock, and roots music by Tin Can Fish Band at Flat Iron Crossroads.
XTRA Home and Garden Showcase
Join WXGM for their 14th annual Home and Garden Show at the Gloucester Moose Lodge.
2026 Restaurant Week
Get ready to savor the flavors of Gloucester! Restaurant Week is returning March 6–15, 2026, and this year promises more delicious discoveries, creative menus, and community spirit than ever before.
The Plate Scrapers at Flat Iron Crossroads
The Plate Scrapers bring progressive bluegrass with a traditional soul to Flat Iron Crossroads, delivering high-energy picking, rich harmonies, and an immersive live show rooted in years of touring and acclaimed recordings.
Pioneers of Progress: Civil Rights Trail Open House
Join us for a special open house celebrating Gloucester’s powerful history and progress!
Rose Cocktail Demo at Zoll Vineyards
Join us at Zoll Vineyards for a lively Rosé Cocktail Demonstration featuring two refreshing creations: a crisp Rosé Spritz and a beautifully balanced Rosé Blush.
Sushi Sunday Funday at Zoll Vineyard
Join us for a delightfully delicious evening as Chef Zoll leads you in one of our most popular cooking classes for Sushi Rolls
Mardi Gras at Flat Iron Crossroads
Celebrate Mardi Gras at Flat Iron Crossroads with high-energy live music from Anthony Rosano and The Conqueroos and The Siren City Horns, festive vibes, and New Orleans–style fun.
Open House & Vendor Market at Brent and Becky's Bulbs
Join Brent and Becky’s Bulbs as they reopen for the 2026 season!
Mardi Gras at Gloucester Brewing Company
Celebrate Mardi Gras at Gloucester Brewing Company with food, music, and lively atmosphere.
Reckoning at Flat Iron Crossroads
Gather at Flat Iron Crossroads for Reckoning, a Greatful Dead tribute band.
Celebration of Love Glass & Resin Craft Night at Zoll Vineyard
Celebrate love in all its forms at Zoll Vineyards with a creative and cozy Glass & Resin Heart Craft Night.
Sunday Funday DIY Watercolor Creation at Zoll Vineyards
his in-person event is all about having fun with watercolor painting, no experience needed. Bring your good vibes and get ready to make some colorful DIY art.
Jeff Little Trio at Flat Iron Crossroads
The Jeff Little Trio brings high-energy Appalachian music to Gloucester—virtuosic piano, award-winning strings, and a dynamic blend of tradition and innovation in an unforgettable live show.
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.