
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.

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.

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.

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.

Gloucester's Play All Day
Join Gloucester’s Play All Day with live music, food truck, and free sunset yoga.

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

Concerts on the Green: Tom Euler
Free concert at Gloucester’s Historic Courthouse Circle! Tom Euler belts out blues and rock with covers and originals.
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!

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!

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.

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!

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’.

The Deloreans at Flat Iron Crossroads
The Ultimate 80s Tribute band is back again! Gear up for The Deloreans on Saturday, July 19th, 2025.

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.

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!

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.

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.

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.

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.

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.

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.

Honor Our Heroes - Pocahontas Foundation
Honor Our Heroes Celebration presented by the Pocahontas Foundation.

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.

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.

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.
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.
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.