Upcoming Events

Gloucester Day Celebration
Join the fourth annual Gloucester Day, where communities named Gloucester from around the world come together to celebrate their shared heritage. At noon, enjoy a live video conversation with leaders and residents from Gloucester, U.K., and other Gloucesters across the globe.

Flat Iron Crossroads Presents Grayson Torrence
Enjoy a night of live music with Richmond vocalist and composer Grayson Torrence, performing with a full band. Food will be available from the food truck starting at 5:30 PM, and drinks will be served at the FIX Bar. The show may be indoors or outdoors, depending on the weather.

Gloucester Farmers Market
The Gloucester Farmers Market takes place the second Saturday of each month, May through October, from 9 AM to 1 PM. Parking is available just past the Historic Church on Route 14 (John Clayton Memorial Highway).

Yorktown Revolutionary Festival
Kick off the afternoon with the Revolutionary Festival (3–7 PM) — a family-friendly event featuring artillery demonstrations, colonial music, living history encampments, kids’ games, militia drills, spy challenges, hands-on history activities, and more. Enjoy live performances throughout the day, including The Colonial Entertainers Guild, Follow the River, and The Fifes & Drums of York Town.

Virginia Wine Camp: Silver Hand Meadery Winemaker Weekend Tastings
Join Camp Cardinal RV Resort for the September 2025 edition of Virginia Wine Camp featuring an intimate guided tasting hosted by Meadmaker (and founder and owner) Glenn Lavender of Silver Hand Meadery.

Fight Cancer: A Free Concert Hosted by the Brush Away Cancer Society
Stop by Main Street on Sept 20 to enjoy live music and support the fight against cancer!
This free concert will feature multiple bands performing, and donations will be set up for fundraising for the Brush Away Cancer Society.

Gloucester Wine Festival
The Gloucester Wine Festival, hosted by the Gloucester County Chamber of Commerce at Brent & Becky’s, is your passport to the best of Virginia wine, food, and music.

Oktoberfest at Gloucester Brewing Company
Raise a stein and celebrate Oktoberfest with Gloucester Brewing Company! Their anticipated Fairfield Fest, a German-style Festbier, will be on tap, while Dominion Dogs will be serving a German-inspired menu all day long.

Concerts On The Green Summer Series
Concerts on the Green - Summer Series 2025!
Get ready for an unforgettable summer of music, community, and fun! Visit Gloucester’s Concerts on the Green features a stellar lineup of local bands, DJs, and artists performing a wide variety of genres.
Here’s the Summer 2025 Lineup:
9/3 | 5:30-7:30PM | Ami Baker Music – Eclectic acoustic sounds
9/17 | 5:30-7:30PM | Just Dan – Classic Sinatra tribute
9/21 | 12:00-5:00PM | Series Finale: Headliner Courthouse Community Orchestra & Guests
Location: Historic Court Circle - 6504 Main Street
Bring your lawn chairs, picnic blankets, and your dancing shoes!
Free & Open to the public.
Visit https://gloucesterva.gov/tourism for more information!

Gloucester Rotary 41st Annual Pig Roast
The Gloucester Rotary invites you to its annual all-you-can-eat barbecue dinner. Tickets are $40 per person, with kids under 6 free. Enjoy good food, fellowship, and a 50/50 raffle.

Guinea Jubilee
The Guinea Heritage Association works to preserve the history and traditions of the unique community of Guinea. Its signature event, the Guinea Jubilee, is Gloucester’s fall festival and draws thousands each year to celebrate life in the Guinea Neck. The two-day event features cultural activities, arts and crafts,, seafood, live music, and fireworks.

Sanders Oktoberfest
Join Sanders for their second annual Oktoberfest celebration. Enjoy a day filled with great food, local beer from Gloucester Brewing Company, unique handmade items from local vendors, and fun activities for all ages.

Homestead Market
Experience Fall at Its Coziest: Homestead Market + Community Yard Sale
Crunchy leaves, crisp air, and the scent of cinnamon in the breeze—Homestead Market is your invitation to slow down and savor the season.

Small Business Saturday
Sandwiched between Black Friday and Cyber Monday, Small Business Saturday offers something a little more personal. On Saturday, November 29, explore the charm of Gloucester Main Street.

Mariposa Medical Spa End-of-Summer Customer Appreciation Event
Join Mariposa Medical Spa for an afternoon of beauty, relaxation, and exclusive specials to celebrate the end of the season.

3 Day Blacksmithing Class
Curious about the art of blacksmithing? Try your hand at the forge with an upcoming class at The Village Blacksmith!

1 Day Blacksmithing Class
Curious about the art of blacksmithing? Try your hand at the forge with an upcoming class at The Village Blacksmith!

RiverJam 2025
RiverJam 2025 promises a toe-tapping, hand clapping, soul soaring collaboration of live music and song featuring performances by The Ballast Band, Don Irwin, Lily Loves Jazz, and One Voice Chorus Richmond. Local food vendors, art activities, and an abundance of FUN FOR ALL!

From Colony To Country
Step into the summer of 1775 with a live historical drama exploring Gloucester’s role in the American Revolution.

Movie on Main: Free Community Movie!
Celebrate the end of summer with Movie on Main!
Join us for a free, community movie night under the stars on the lawn at The House of Ren, right in the heart of Gloucester’s Main Street. This year’s feature film is Disney-Pixar’s Ratatouille — the perfect recipe for a fun evening with family, friends, and neighbors.
Before the movie begins, the fun kicks off at 5:00 PM with family-friendly trivia beginning at 5:30 PM, plus snacks and drinks available for purchase, including selections from Gloucester Brewing Company. Bring a blanket or chair, find your spot, and settle in for a relaxed and memorable night.
We’re also hosting a Teacher Supply Drive to support Botetourt Elementary teachers. Donations of school supplies are encouraged, with the most-needed items including:
Expo markers
Post-it notes
Small whiteboard erasers
Large packs of colored paper
Tissues
Bring a teacher supply item or donate to be entered into a raffle featuring prizes from local Main Street businesses. Donations will be accepted on site during the event, or you can drop them off early at our office (6882-G Main Street) and receive your raffle ticket in advance.
Experience a movie among murals, soak in the charm of Main Street, and help us celebrate summer with a night full of heart, community, and creativity.
Interested in getting involved? Explore our sponsorship opportunities or sign up to volunteer — it’s a great way to support this special community event and be part of the fun!

Upcycled Art for Humanity at York & Main
York & Main will host “Upcycled Art for Humanity”, featuring local artists transforming Habitat ReStore items into unique works of art.

July Talks About Uniquely Gloucester Topics
The Gloucester Women’s Club is thrilled to bring back their popular Summer Series for 2025 – and you’re invited!

July Talks About Uniquely Gloucester Topics
The Gloucester Women’s Club is thrilled to bring back their popular Summer Series for 2025 – and you’re invited!

Timeless Treasures Ribbon Cutting
Join us in welcoming Timeless Treasures, Gloucester Main Street’s newest shopping destination featuring antiques, handcrafted goods, furniture, and one-of-a-kind finds.
Celebrate their grand opening with a ribbon-cutting ceremony and explore their unique booths showcasing local vendors and collectors.
Stop by and discover what treasures await!

July Talks About Uniquely Gloucester Topics
The Gloucester Women’s Club is thrilled to bring back their popular Summer Series for 2025 – and you’re invited!

Food Truck Frenzy
Mark your calendars for Sunday, July 13, 2025, from 1-5 PM, and head to the heart of Gloucester for an unforgettable experience! The Food Truck Frenzy will bring together food lovers, families, and fun-seekers for a nautical-themed celebration at the Old Page Grounds on Highway 17.

PJ Party at The Cereal Plug
The Cereal Plug is serving up fun, flavor, and a little friendly competition on Gloucester Main Street!
Enjoy $3.50 bowls of cereal and milk, $4 waffle pairs, or $6 cereal waffles topped with whipped cream, sprinkles, more cereal, and your choice of syrup. They’ll also be offering $3 ice cream scoops and $4 quarter-pound hot dogs with chips!
Come dressed in your pajamas and snap a pic for their pajama contest—one lucky winner will score a $20 Cereal Plug gift card! (Photos are optional.)

July Talks About Uniquely Gloucester Topics
The Gloucester Women’s Club is thrilled to bring back their popular Summer Series for 2025 – and you’re invited!

Porter's on Main: Ribbon Cutting Celebration
Join Porter’s on Main as they mark an exciting new chapter on Main Street with an evening of connection, community, and celebration. Tuesday, July 1st, we invite you to the Ribbon Cutting Ceremony and Cocktail Hour to include Hors d'Oeuvres, Refreshments, Craft Cocktails, Wine & Beer at Porter’s Cash Bar.
Take this opportunity to meet the management team at Porter’s - Executive Chef Joshua Hutter, General Manager Jeff Brown, and Head of Beverage Service & Mixologist Matthew Martin. You might even meet Porter himself! Let’s raise a glass to what’s ahead.
See you there!
Doors will open at 5:15 pm, and the Ribbon Cutting will be at 6:00 pm.
RSVP encouraged.

It's A Wrap Reception
The 2025 Heart of the River Collection will be on display at the Fine Arts Museum of Gloucester from June 15th through June 28th. Don’t miss this fun end to the events of the 2025 Festival and the last chance to purchase a painting before they leave for good!

Art in the Village
Come for the day and stay! Experience a truly unique family-friendly day at Art in the Village along Gloucester Main Street. What’s in store? An Artisan Fair in the Courthouse Circle, pop-up art classes for all ages and live music at Arts on Main, art demonstrations at York & Main, explore the new community art space at ArtWork, and show your creative side on the Community Art Mural.

Traces of Transformation
Exciting for 2025, York & Main proudly presents an art exhibition that is set to inspire and engage the community.

Arts at Abingdon
Presented in partnership with Gloucester Arts Festival and The Cook Foundation, during June, Arts at Abingdon presents the SOMA Quartet. Join us for a music-filled evening at the historic Abingdon Church. All concerts are free of charge. Reservations are not required.

Juneteenth Celebration at The Cereal Plug
Celebrate Juneteenth at The Cereal Plug with good food, good music, and good company—open to everyone, and happening in a space open to everyone.
Whether you're stopping by for a bite or staying to dance, it’s a great way to experience and honor Juneteenth in a joyful, inclusive setting.
Follow The Cereal Plug on Facebook for updates on the menu and specials.

Juneteenth Celebration
Juneteenth holds a special significance in the African American community. It’s not just the commemoration of the end of slavery for people of African descent in America; it is an affirmation of the power that we possess to impact positive change. Celebrating Juneteenth demonstrates that, in spite of the most painful parts of our American history, African Americans refuse to be held down by the past and are determined to move forward towards a free and equal present and future.
Join us in recognizing Opal Lee, the “Grandmother of Juneteenth,” who played a key role in making June 19th a national holiday during our annual Opal Lee Walk which starts at 9:00 AM at the Gloucester County Main Library. Followed by the celebration at Holly Knoll starting at 1:00pm. Admission is free.

Gloucester Arts Festival Plein Air Gala
Mingle with the talented Plein Air artists of the Gloucester Arts Festival while relishing a glass of sparkling wine and savoring an array of delicious heavy hors d'oeuvres. Take your time to peruse all the stunning paintings created throughout the week and seize the opportunity to purchase your favorite piece!

First-Ever Book Signing at The Nook
Join The Nook for their very first book signing event! Meet local author Patti Procopi and get your signed copy of The Murderer You Know—a must-read for true crime podcast fans and mystery lovers alike.
Enjoy the welcoming atmosphere of The Nook, browse their latest book arrivals, and support a local business and author. Whether you're a dedicated reader, a supporter of all things local, or just looking for something new to explore, this is an event for you!

Patron Preview Party
Get ready for an unforgettable experience in 2025 with the debut of the Gloucester Art Festival’s Patron’s Preview Party! An exclusive soirée for art patrons will be held at historic Dixondale Wharf, offering a unique opportunity to select a painting created by talented plein air artists before the lottery at the upcoming gala.
You must be a Patron to attend. Secure your spot at this special early access event by purchasing your Patron Ticket here.

Loving Day Dedication
Join us on Thursday, June 12, at 2:00 PM for the unveiling and dedication of Gloucester’s new LOVEWorks sign, located on the gazebo lawn at Sanders Riverside Active Living Community, just off Main Street.

Symphony Under the Stars
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. The evening will begin at 6pm with a performance by Gloucester’s very own The Liberty Dolls!

Paint Main
On Saturday, June 7th, the 2025 Plein Air festival painters will compete in a fast-paced paint-out along Main Street from 10 a.m. to noon.
Community painters are also welcome to register for this Paint Main event and compete for separate prizes. Judging will follow on the Tabb House Lawn. After prizes for both groups have been awarded, the paintings will be available for sale fresh off the easel - and ready to hang in your home!

Brews, Brine & Wine
Enjoy oysters, beer, wine and new this year, whiskey! Visit the Plein Air artists from the Gloucester Arts Festival who will interpret the beautiful surroundings on their canvases, creating small works available for sale at the event. Art, food, music and beautiful scenery will make for a lovely evening for the whole family. Co-hosted with the Fairfield Foundation.

Movie & Treats Night with The Nook and The Cereal Plug
The Nook and The Cereal Plug are teaming up for a special Movie & Treats Night on Main Street! Bring the family, grab your favorite snacks from The Cereal Plug before the movie starts at 8:00 PM, and settle in for a free outdoor showing of Luca—a fun, family-friendly movie with summer vibes.
The Cereal Plug will have treats, hot dogs, drinks, and special snack bundles available for purchase.
Admission is free. Don’t forget to bring your lawn chairs!
Come enjoy a relaxing evening under the stars on Gloucester Main Street!

Kids Karaoke at The Cereal Plug
Get ready for a fun-filled afternoon at The Cereal Plug’s Kids Karaoke!
Kids can take the mic and sing their favorite songs, then cool off with ice cream piled high with toppings, cereal treats, and more. Specialty snack bowls will also be available for purchase.
Bring the family, grab a treat, and enjoy a sweet Main Street moment!