UPCOMING EVENTS
The Jared Stout Band at Flat Iron Crossroads
Join us in Gloucester, VA to hear The Jared Stout Band, an alt-country powerhouse based out of Southwestern, Virginia.
Secondhand Saturdays
Discover Hidden Treasures Every Saturday in March: Join Gloucester’s Secondhand Saturdays!
Mardi Gras with The Travis Colby Band at Flat Iron Crossroads
Join us on Saturday, March 1st for an indoor fun and festive set of New Orleans music by The Travis Colby Band. The doors open at 5:30pm with the show starting at 6:30pm.
Mardi Gras at Gloucester Brewing Co
Mardi Gras celebrations are in the air, so dig out those masks and beads and don your best Mardi Gras wear!
Gumbeau's Catering will be on site serving classic Southern Louisiana dishes, and other bayou classics...stay tuned for the full menu.
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!
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.
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.
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.
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.
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.
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.
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!
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.
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.
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!
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!
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.
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'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.
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.
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.
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.
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.
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.
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.
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.
Underground Railroad: Songs Of Freedom
Sing Underground Railroad Songs of Freedom along with the men of The First United Baptist Church and support the Gloucester High School Ensemble as they sing Black History songs.
Last Fair Deal at Flat Iron Crossroads
Join us on Saturday, February 15th for an indoor, acoustic experience with Grateful Dead Tribute Band, Last Fair Deal. The doors open at 5:30pm with the show starting at 6:30pm.
Sushi Making Class with Chef Zoll
Learn to make a California Roll, Spicy Creamy Crab Roll, Avocado Shrimp Spring Rolls, Kimchi Cucumber Roll at Zoll Vineyards!
Brent and Becky's Open House & Vendor Market
Come celebrate Brent and Becky’s spring opening with special deals and local vendors.
Valentine's Cheese & Wine Paring Zoll Vineyard
Join Chef Zoll as he walks you through a 5 course pairing of his favorite sweet & savory plates. Pairing starts at 6 pm doors open at 5:30 pm.
Galentine's Crafting Party at York and Main
Indulge in a Galentine's Day of Crafting Bliss at York & Main!
Join York & Main for an afternoon of creativity, camaraderie, and chocolate as we celebrate Galentine's Day with a special crafting party
Find Love On Main
Join Gloucester Main Street for their Find LOVE on Main Scavenger Hunt!
The Lafayette Bicentennial & Gloucester County
Join Robert Kelly, Director of the Gloucester Museum of History & Vice President of the American Friends of Lafayette, for a discussion about General Lafayette's legacy, that includes connections to Gloucester.
Christmas at Ware - Gloucester Farmer's Market
The Gloucester Farmers Market presents Christmas at Ware! Enjoy 70+ vendors, ready to celebrate Christmas with you on the beautiful Campus of Ware Church.
Waiting For Washington at The Edge Hill House
Christmastide is a time when families gather and there is nothing more Lady Washington wants than to have her General home from the War. Join Martha Washington and her daughter-in-law, Eleanor, in December of 1783, as they wait for the General and discuss Christmastide traditions, family, and Eleanor’s marriage to David Stuart.
2024 Christmas & Holiday Parade
The 2024 Christmas & Holiday Parade on Main Street is a festive celebration that brings the community together to kick off the holiday season. Join us for an enchanting afternoon filled with twinkling lights, joyous music, and creative floats as they make their way down Main Street.
Festival of Trees
Join us as Main Street turns into a holiday wonderland full of joy, kindness, and support for the many nonprofits, businesses, and government organizations that help make our community great.
Arts on Main Small Works Show & Holiday Marketplace
Support a small, local business this holiday season by gifting your loved one a present that is unique and handmade!
Sentara Timberneck Turkey Trot 5K Run/Walk Fundraiser
Run or walk this scenic, flat, paved 3.1-mile loop course at Machicomoco State Park in Gloucester, Virginia. Water will be available at the start/finish line, as well as as the halfway point of the race route. Public restrooms will also be available near the race finish.
Celebrating Gloucester's Veterans- Second Sunday Series
Celebrating Gloucester’s Veterans Program
Come together to celebrate and honor the bravery and dedication of Gloucester’s veterans in this heartfelt gathering of remembrance and gratitude.
Party on the Half Shell- A Virginia Wine & Oyster Pairing Experience
Join us at Camp Cardinal RV Resort for "Party on the Half Shell – A Virginia Wine & Oyster Pairing Experience.
Sip & See Harvest Festival- Kelsick Specialty Market
Join us for the Sip & See Harvest Festival at Kelsick Specialty Market on November 1st! 🍂🍷 Celebrate the flavors of fall with seasonal sips, delicious bites, and festive fun.
1st Fridays on Main Street
First Fridays on Main Street: A Night to Shop, Stroll, and Savor in Gloucester, VA!
Memorial Dedication Ceremony- Honoring French Soldiers
Join us as we dedicate a memorial in honor of the French soldiers who died at the Battle of the Hook.
Celebrate Indigenous People's Weekend at Machicomoco State Park
Join our friends at Machicomoco State Park to celebrate Indigenous People's Day weekend! Activities for the Second Sunday Series start at 10AM and include learning about artifacts, learn the basics of archery (call Ranger Station to register- 804-642-2419), and weave your own pine needle basket!
Walter Reed Birthplace : Guided Tours
Discover History: Tours at Walter Reed's Birthplace Presented by The Fairfield Foundation
Wine Maker Barrel Tasting
Join Chef Zoll owner & award winning vintner on Sunday September 29th at 1 pm as we sample the new releases of sangria and barrels from 2023 vintage.
Oktoberfest at Gloucester Brewing Co
Mark your calendars for a fantastic Oktoberfest celebration at Gloucester Brewing Company on Sunday, September 29th!
Live Music by Bubba Ward - YROC
Join us for live music on the deck with Bubba Ward! Check him out on Facebook.
The 2024 Guinea Jubilee
Save The Date!
The Guinea Heritage Association’s mission is to preserve the history and values of the unique community called Guinea.
Music In The Park - Machicomoco State Park
Come join us on Saturday September 21, 2024 from 5:30-8:00 pm for MUSIC IN THE PARK!
2024 Gloucester Wine Festival
Featuring top Virginia Wineries, live music, fine foods, art and retail vendors.There will also be Wine Tasting and Educational Seminars. Parking will be at Ware Academy with convenient shuttles.
Juan's Taco & Beer Festival
Taco & Beer Festival at Juan’s Cafe & Cantina on Sep 17, 4-9 PM! Tacos, beer, live music, and more. Free for kids
Virginia Homegrown Bluegrass Festival
Flat Iron Crossroads is bringing together three Virginia based bluegrass band on Saturday, 9/14/2024 to feature Rappahannock Crossing, Bill Jenkins & The Virginia Mountain Boys, and The Tidewinders headlining!!