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.
Good Shot Judy at Flat Iron Crossroads
The Mid-Atlantic’s No. 1 high octane swing band, Good Shot Judy is performing in Gloucester, VA at Flat Iron Crossroads!
July Talks: Native Plants - They Have Always Been Here
Each week, explore the rich history, vibrant culture, and hidden stories of Gloucester – with guest speakers, lively discussions, and plenty of community spirit.
Jerry Fest: The Days Between at Flat Iron Crossroads
Join us as we honor the legacy of Jerry Garcia and the music he helped bring to life with Kooler Heads, Stellar Rose, and WOLPH!
Concerts on the Green: DJ Big-E Diceman
Free concert at Gloucester’s Historic Courthouse Circle! DJ Big-E Diceman spinning your favorite pop, rap, and hip-hop classics.
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.
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.
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!
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.
Celebrate National Honey Bee Day at Brent and Becky's Gardens
Celebrate all things Honey Bee at Brent and Becky’s!
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.
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.
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.
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.
RiverJam
Arts on Main’s 9th annual RiverJam hosted by Flat Iron Crossroads playing all your favorite live music.
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.
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.
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.
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.
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.
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..
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!
July Talks: Building A Bridge Over The York - Connecting The Two Peninsulas
Each week, explore the rich history, vibrant culture, and hidden stories of Gloucester – with guest speakers, lively discussions, and plenty of community spirit.
Concerts on the Green: Nathan Stephenson
Free concert at Gloucester’s Historic Courthouse Circle! Tom Euler belts out blues and rock with covers and originals.
The Deloreans at Flat Iron Crossroads
The Ultimate 80s Tribute band is back again! Gear up for The Deloreans on Saturday, July 19th, 2025.
July Talks: Country Stores Are Still Surviving- Nuttall’s & Bucks
Each week, explore the rich history, vibrant culture, and hidden stories of Gloucester – with guest speakers, lively discussions, and plenty of community spirit.
Garden Walk with Brent Heath of Brent and Becky's Bulbs
Explore Brent and Becky’s gardens on this guided tour with Brent!
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’.
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.
Willie Williams Band at Flat Iron Crossroads
Roots Rock, Southern Americana, and Country Soul artist, Willie Williams, is bringing the band to Flat Iron Crossroads!
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: 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.
July Talks: Natural Treasures Under Our Water-Underwater Mining Is Not A New Venture
Each week, explore the rich history, vibrant culture, and hidden stories of Gloucester – with guest speakers, lively discussions, and plenty of community spirit.
Concerts on the Green: Toby and Larry
Free concert at Gloucester’s Historic Courthouse Circle! Toby and Larry will be setting the summer stage with your classic peaceful beach vibes. Location Change: Museum of History back lawn!
July Talks: Local Steamboats- Moving Good & People Around Eastern Virginia
Each week, explore the rich history, vibrant culture, and hidden stories of Gloucester – with guest speakers, lively discussions, and plenty of community spirit.
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!
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.
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.
Concerts on the Green: Tom Euler - Cancelled
Free concert at Gloucester’s Historic Courthouse Circle! Tom Euler belts out blues and rock with covers and originals.
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
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
Gloucester's Play All Day
Join Gloucester’s Play All Day with live music, food truck, and free sunset yoga.
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.
Juneteenth Celebration at Holly Knoll
Join us for a Family-Friendly event that educates, recognizes, and demonstrates the importance of this hallowed day in American History. There will be a dynamic program and speaker, educational displays, children’s hands-on learning activities, games, vendors, music, and food. Admission is free.
Lord Nelson Band at Flat Iron Crossroads
Flat Iron Crossroads hosts Lord Nelson Band, an original rock and roll set from the foothills of Virginia’s Blue Ridge Mountains.
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.
Gloucester Summer Kick-Off Carnival
BONUS WEEEKEND ADDED! 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.
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.
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.
Reggae Fest at Flat Iron Crossroads
Flat Iron Crossroads is hosting Reggae Fest on Saturday, June 7th featuring Stuck on a Name, Lions Bridge, and headliner, Mighty Joshua to spread peace and love through music and community.
Paint Main- Gloucester Arts Festival
Watch 30 nationally recognized plein air artists and local talents capture the essence of the historic district.
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.