SPECIAL EVENTS
Rosewell Tours
Your visit to Rosewell starts at the Visitor Center. Here, you will find educational exhibits and artifacts in the Gallery, along with a short orientation video that gives you a look at Rosewell's complex past and a vision of future goals.
Marine Science Day 2025 - VIMS
Join us for the annual VIMS open house- a fun-filled and educational event for the whole family! Located on Gloucester Point, MSD features exhibits, children's activities, seining in the York River, tours, a seafood cooking demonstration, mini-lectures, and more.
Dedication of Remembrance Structure at Rosewell
A dedication service will be held at Rosewell on Sunday, June 1 at 3 pm to celebrate past resilience and embrace renewal at the Remembrance Structure constructed on the manor’s north side.
Brews, Brine & Wine - Gloucester Arts Festival
Enjoy oysters, beer, wine and new this year, whiskey! Visit the Plein Air artists who interpret the beautiful surroundings on their canvases, creating small works available for sale at the event.
Paint Main- Gloucester Arts Festival
Watch 30 nationally recognized plein air artists and local talents capture the essence of the historic district.
Symphony Under the Stars- Gloucester Arts Festival
The June 7th 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.
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.
Gloucester Summer Kick-Off Carnival
This thrilling celebration marks the end of the school year and the start of long, lazy summer days—with classic carnival rides, exciting games, a kid’s play zone, and mouthwatering fair food that’ll transport you straight to summertime nostalgia.
Timberneck Open House
Come visit the Timberneck House, a late 18th-century home owned by the Catlett family for generations until the early 20th century.
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.
Winemaker Weekend: Rosemont of Virginia
Featured winemaker will stay at Camp Cardinal, giving guests plenty of opportunities to ask questions, share stories and deepen their appreciation for Virginia wine.
Traces of Transformation
Traces of Transformation, presented during the Gloucester Arts Festival, brings you deep into the influence the world around us has on artists.
Art by local Theresa Wells Stifel
The English Channel at Flat Iron Crossroads
America’s premier British Invasion band performing British pop, rock & prog hits of the mid 60’s & 70’s
Timberneck Open House
Come visit the Timberneck House, a late 18th-century home owned by the Catlett family for generations until the early 20th century.
Art in the Village- Gloucester Arts Festival
Art in the Village is a full day of fun for the whole family. Come for the day and stay for dinner at one of Main Street’s eateries.
Anthony Rosano and the Conqueroos at Flat Iron Crossroads
Join us in Gloucester, VA on 6/28 to hear Anthony Rosano and the Conqueroos mix traditional Blues and Roots elements with a modern Rock delivery featuring Ron Holloway, saxophone extraordinaire!
Winemaker Weekend: Gauthier 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.
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.
Food Truck Frenzy
Celebrate summer in the heart of Gloucester! It’s a foodie's paradise with gourmet food trucks, live music, craft vendors, boat show, and kid's activities.
A Front Row Seat to American Victory in Yorktown
Join us at Buck’s Store Museum as we are treated to little known stories and secrets of ‘Little England’.
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.
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.
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.
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.
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.
Timberneck Open House
Come visit the Timberneck House, a late 18th-century home owned by the Catlett family for generations until the early 20th century.
Freedom Junction at Flat Iron Crossroads
Join us in o hear Nashville’s funk-rock jam band, Freedom Junction.
Lucid Evolution at Flat Iron Crossroads
Join us to hear Lucid Evolution, a funk-rock jam band from Richmond.
Lavender Tea Party
The perfect way to celebrate Mother’s Day or simply enjoy a delightful afternoon with friends.
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.
Timberneck Open House
Come visit the Timberneck House, a late 18th-century home owned by the Catlett family for generations until the early 20th century.
Pressing Strings
Returning to Flat Iron Crossroads is Pressing Strings, a four-piece band based out of Annapolis, Maryland performing a blend of indie, soul rock, and Americana roots.
The Bobby Thompson Trio at Flat Iron Crossroads
The Bobby Thompson Trio performs originals, blues, rock, and related styles and is based in Washington D.C.
Gloucester's Showcase in Historic Garden Week
Tour the beauty and history of Gloucester County abound in its rivers and exquisite shoreline homes.
Timberneck Open House
Come visit the Timberneck House, a late 18th-century home owned by the Catlett family for generations until the early 20th century.
Historic Garden Week Celebration at Brent & Becky's
Celebrate spring during the Gloucester-Mathews Historic Garden Tour at Brent and Becky’s. The Gloucester Master Gardeners will be giving tours of our gardens throughout the day. Come join the fun!
Earth Day Celebration at Machicomoco State Park
Join us on April 19th for a fun and educational event where you can connect with our Clean Community Coordinator and many other local partners to learn how YOU can make a difference in preserving our planet.
Gloucester Arts Festival Book Fair
Join us at from 10:00am to 3:00pm at The Fine Arts Museum of Gloucester for the first annual Gloucester Arts Festival Book Fair as we celebrate the literary arts.
Brasswind at The Daffodil Festival
The incredible Brasswind band will be taking the Main Stage at the 2025 Daffodil Festival on Sunday, April 6th, from 12 PM to 4 PM!
The Mullins Sisters - 2025 Daffodil Fesitval
The Mullins Sisters will be performing live at the 2025 Daffodil Festival on the Main Stage, sponsored by Gloucester Toyota!
Sippin on the Street at Kelsick Market
Join us for a fun day of live music, food and drinks during the 2025 Daffodil Festival!
Bulb Tours at Brent and Becky's
Join Brent and Becky’s, celebrating their 125th anniversary, with a behind the scenes tour of their facility and elaborate gardens during the Daffodil Festival.
2025 Gloucester Daffodil Festival
Celebrate the beauty of spring at the 2025 Daffodil Festival in Gloucester, Virginia! This beloved annual event, themed "It's All Sunshine & Daffodils," will take place on the first weekend in April, transforming Main Street into a vibrant display of yellow blooms and festive activities.
2025 Gloucester Main Street's Beer Garden
Get ready for the first-ever all weekend Beer Garden on Gloucester Main Street!
A weekend of family-friendly activities, including a dedicated kids’ zone, live music, craft beers, and food trucks!
VA250 Mobile Museum at The Daffodil Festival
We are thrilled to announce that the new VA250 Mobile Museum will be coming to our beautiful town! We've been selected by the VA250 - American Revolution 250 Commission to host this incredible traveling exhibit, and we can’t wait to share it with you!
Blues Flash at Flat Iron Crossroads
Join us on Saturday, March 29th for Blues Flash, playing a variety of blues inspiration with a touch of county, old rock & roll, and a hint of Elvis. The doors open at 5:30pm with the show starting at 6:30pm.
Art on Tap at Gloucester Brewing Co
This event will spotlight local artists and artisans, showcasing a vibrant array of handmade and locally sourced goods.
Women's History Month Brunch at Holly Knoll
Join us for this special event honoring the remarkable contributions of African-American women to the Commonwealth of Virginia and our nation.
She Made History- Honoring Remarkable Women of Gloucester
Join us for an inspiring program celebrating the remarkable women who made their mark on history right here in Gloucester.
St. Patrick’s Day with Poisoned Dwarf at Flat Iron Crossroads
Join us on Saturday, March 15th for traditional Irish and Scottish music by Poisoned Dwarf on acoustic instruments. The doors open at 6:00pm with the show starting at 7:00pm.
Mary Shipko - Avaiatrix First Woman Pilot for Hughes Airwest
Mary Shipko is featured on the mural of the Pioneering Women of Gloucester, and she is coming to the Main Library on March 9 for a presentation and book signing.
Women's Empowerment Program
Join us at the Fine Arts Museum of Gloucester for an inspiring afternoon celebrating women's voices in the arts!On March 9th, from 1:00 PM to 3:00 PM, we’re hosting a powerful Women's Empowerment Program
Buffalo Rose at Flat Iron Crossroads
Join us on Saturday, March 8th for the charismatic six-piece modern/folk Americana band from Pittsburg, PA. The doors open at 5:30pm with the show starting at 6:30pm.
2025 Gloucester Restaurant Week
2025 Gloucester Restaurant Week is Coming!
Mark your calendars for March 3rd–9th, and get ready to savor the best of Gloucester’s local dining scene! Join us for a week filled with exclusive menus, delicious specials, and exciting offers from your favorite eateries around town. It’s the perfect chance to try something new or enjoy a twist on a classic dish—all while supporting our amazing local restaurants!
ready to treat your taste buds to something unforgettable!
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.