SPECIAL EVENTS
Liam Pucell and Cane Mill at Flat Iron Crossroads
Characterized by No Depression as “the future of bluegrass”, Liam Purcell & Cane Mill Road twine innovation, tradition, and excellence into a unique musical experience.
Timberneck Turkey Trot 5K/Walk
Join us for the 6th ANNUAL Timberneck Turkey Trot 5k Run/Walk Fundraiser, hosted by the Fairfield Foundation.
Gloucester Christmas and Holiday Parade
Kick off the holiday season with the Christmas & Holiday Parade & Annual Tree Lighting!
Jeff Little Trio at Flat Iron Crossroads
Mixing Appalachian traditions and an innovative edge, the Jeff Little Trio delivers high-energy shows fueled by amazing musicianship.
Daffodil Dash 5K & Fun Run
Celebrate spring in Gloucester with the Daffodil Dash 5K and NEW 1-Mile Fun Run
River & Bay 5k
Join us in Gloucester Point on the VIMS & Batten School campus for the inaugural River & Bay 5K!
Galloween at The LC Salon
Grab your best costume and gather your favorite girls for a spooktacular girls' night out at The LC Salon!
Coyote Rodeo at Flat Iron Crossroads
Coyote Rodeo is an Asheville, North Carolina–based experimental bluegrass band built around the songwriting of John Colby Elswick (guitar/banjo), Chad Brown (mandolin) and Connor Kozlosky (Guitar).
The Bruce Katz Band at Flat Iron Crossroads
Bruce Katz is a legendary keyboardist (Hammond B3 and piano) who has released 12 CDs as a leader and has appeared on nearly 80 other CDs with the likes of John Hammond, Delbert McClinton, Ronnie Earl, Butch Trucks, Duke Robillard, Little Milton, Joe Louis Walker, David “Fathead” Newman, and many, many others.
Fall Book Fair at The Nook
We’re bringing together an amazing group of local makers, artists, and bookish vendors alongside all the books you already love at The Nook.
Common Cause: The Constitution of Virginia 1776
Experience history firsthand through an interactive living history presentation that brings the birth of the Commonwealth to life.
African American History: Glimpse of the Past
Join us for an engaging discussion that brings to life the African American people, places, and experiences that helped shape our community.
Gloucester Wine Festival
One of Gloucester’s favorite fall traditions- the annual Wine Festival!
RiverJam 2026 by Arts On Main
Enjoy great music from the Ballast Band, Edison & Company, and RaJazz! Try delicious food from local vendors and plan for lots of fun and dancing!
Gloucester Farmers Market at Historic Ware Church
Gloucester’s best pop-up market, every 2nd Saturday May through September.
Artist Talk with Michael Rosato: Fine Arts Museum of Gloucester
Go behind the scenes with internationally recognized muralist Michael Rosato as he shares the story behind Six Scenes, One Place, the monumental mural created for the Fine Arts Museum of Gloucester.
Mural Dedication
Join us for the official dedication of Gloucester's newest public artwork.
Pickle Festival at Zoll Vineyard
Get ready for the Pickle Festival at Zoll Vineyards—a day packed with dill-icious fun, great food, refreshing drinks, and unforgettable memories!
Summer Mocktail Class : Zoll Vineyards
Beat the Heat with a Summer Mocktail Class at Zoll Vineyards! Looking for a fun girls' night, date night, or evening out with friends? Join us for a refreshing Summer Mocktail Class where you'll learn to create delicious, alcohol-free beverages that are perfect for every occasion!
Recipes for Immunity : Zoll Vineyard
Join herbalist, Amanda Carpenter, in crafting these foundational tonics rooted in folk herbalism, traditionally used to boost your immunity.
Concerts On The Green : Van Hutchins
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.
Food Truck Frenzy
Fresh flavors, coastal vibes, family fun, music, and summer memories.
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.
Gloucester Farmers Market at Historic Ware Church
Gloucester’s best pop-up market, every 2nd Saturday May through September.
Seward Johnson Sculpture Walk by Gloucester Arts Festival
Sculpture enthusiasts rejoice as the exquisite masterpieces of renowned artist Seward Johnson make a dazzling comeback to the Gloucester Arts Festival.
The Great Community Yard Sale at Brent and Becky’s Bulbs
Join us for a fun-filled day of bargain hunting at the gardens of Brent and Becky’s!
Sports Star Screening by Gloucester Arts Festival
Let’s go to the movies! Join us for the 18 minute film with Gloucester native Ellis Finney, its writer/director, and Jeff Lichtenstein, the movie’s producer.
Fathers Day Celebration - Zoll Vineyards
Join us at Zoll Vineyards for a Fathers Day Celebration!
Gloucester Arts Festival Book Fair
The Book Fair is expected to draw book lovers, families, and community members of all ages, celebrating the vibrant literary scene in Gloucester and its surrounding areas.
Arts at Abingdon by Gloucester Arts Festival
Part of the music series spanning over 37 years, Arts at Abingdon offers a collection of concerts featuring artists from many parts of the globe. All concerts are free of charge.
Gloucester Summer Kick-Off Carnival
Gloucester’s second annual Summer Kick-Off Carnival is the perfect place for thrills and memories
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.