Upcoming Events

Halloween decorations including a clown mask, a purple chair, a pumpkin with a jack-o'-lantern face, and pumpkins with flowers outside a storefront.
A man dressed as Santa Claus with a white beard, glasses, and a red suit with white trim holding a young child in a red and black plaid shirt sitting on his lap. A girl in a pink sweater with Christmas decorations sits next to Santa, smiling. Behind them is a decorated Christmas tree with ornaments and lights, and festive holiday decorations. To the left, a stuffed teddy bear dressed in a blue outfit with yellow accents sits in a red bag.
A hand holding a can of drinks in a blue koozie that reads "Last Call" with a sun and wave design, at an outdoor event on a sunny day.
Gloucester Day Celebration
Sep
6

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.


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Flat Iron Crossroads Presents Grayson Torrence
Sep
9

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.

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Gloucester Farmers Market
Sep
13

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).

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Yorktown Revolutionary Festival
Sep
19

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.

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Concerts On The Green Summer Series
Sep
21

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!

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Guinea Jubilee
Sep
26
to Sep 27

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.

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Sanders Oktoberfest
Oct
4

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.

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Homestead Market
Oct
19

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.

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Small Business Saturday
Nov
29

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.

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RiverJam 2025
Aug
23

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!

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Movie on Main: Free Community Movie!
Aug
16

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!

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Timeless Treasures Ribbon Cutting
Jul
18

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!

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Food Truck Frenzy
Jul
13

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.

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PJ Party at The Cereal Plug
Jul
12

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.)

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Porter's on Main: Ribbon Cutting Celebration
Jul
1

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.

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It's A Wrap Reception
Jun
28

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!

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Art in the Village
Jun
28

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.

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Arts at Abingdon
Jun
19

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.

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Juneteenth Celebration at The Cereal Plug
Jun
19

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.

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Juneteenth Celebration
Jun
19

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.

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Gloucester Arts Festival Plein Air Gala
Jun
14

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!

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First-Ever Book Signing at The Nook
Jun
14

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!

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Patron Preview Party
Jun
12

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.

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Loving Day Dedication
Jun
12

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.

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Symphony Under the Stars
Jun
7

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!

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Paint Main
Jun
7

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!

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Brews, Brine & Wine
Jun
6

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.

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Movie & Treats Night with The Nook and The Cereal Plug
May
9

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!

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Kids Karaoke at The Cereal Plug
May
4

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!

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