Upcoming Events

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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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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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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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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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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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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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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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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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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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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Historic Garden Week in Gloucester 2025
Apr
26

Historic Garden Week in Gloucester 2025

  • 3201 Leadership Drive Naxera, VA, 23061 United States (map)
  • Google Calendar ICS

Organized by the Garden Club of Virginia, Historic Garden Week is the only statewide house and garden tour in the nation. It offers visitors a chance to tour inspired homes and private landscapes, public gardens, and historic sites across Virginia. In addition, more than 1,000 world-class floral arrangements adorn the houses.

The Gloucester tour, presented by the Garden Club of Gloucester and Mathews, includes access to three amazing waterfront properties. Visitors will enjoy the warmth and tradition of two homes along the North River, Exchange (early 1700s) and Blythelea, as they walk between the grounds, taking in the views and gardens. A third home, Holly Knoll, was built in grand Georgian style on the York River for the second president of the Tuskegee Institute, Dr. Robert Moton. It was designed as a place to gather, mentor, and support national civil rights leaders. As a result, it received National Historic Landmark designation and now operates as the Gloucester Institute, a training ground for tomorrow’s African American leaders.

• $50 pp sold online 
• $60 pp day-of-tour ticket 
• Ticket includes admission to 3 homes and 1 museum

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Gloucester Brewing Company: Pints for Parkinson’s Fundraiser
Apr
19

Gloucester Brewing Company: Pints for Parkinson’s Fundraiser

Join Gloucester Brewing Company for an all-day fundraiser to raise awareness and support finding a cure for Parkinson’s.

The day kicks off at 11:00 AM with a family-friendly, 1-mile fun run up and down Main Street. Enjoy live music, a silent auction, and delicious food throughout the day!

For more information, or if you’re interested in sponsoring or donating, please email globrewco@gmail.com or visit globrewco.com.

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2025 Gloucester Restaurant Week
Mar
3
to Mar 9

2025 Gloucester Restaurant Week

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.

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Blessing of the Ground
Mar
2

Blessing of the Ground

A ceremony of sorrow and rejoicing will be offered at Rosewell Plantation on Sunday, March 2, at 3 PM, to consecrate the site where a Remembrance Structure will be built to recognize those who were held in bondage there from the colonial period until Emancipation.

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A Taste of the Arts
Feb
22

A Taste of the Arts

Arts on Main is excited to explore the creative culinary arts with you this February!

The event includes a casual evening of tasty small plates from area caterers and restaurants, complimentary (2) beverages, a signature cocktail cash bar and ample seating. Join in the fun at the chef’s photo booth and enter a chance to win an Arts on Main art class for two!

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Find Love on Main Street
Feb
8

Find Love on Main Street

This scavenger hunt is a fun challenge for everyone—whether you’re teaming up with a partner, friends, family, or flying solo! If you’re going solo, you can team up with others for more fun.

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Italian Wine & Dinner
Jan
25

Italian Wine & Dinner

Kelsick Specialty Market is excited to present an Italian Wine Dinner on Saturday, January 25th, from 6 to 8 PM. Enjoy a delightful evening featuring classic Italian dishes and wines. Indulge in a 4-course meal paired with 4 wines. Purchase your tickets here!

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Animal Kindness Workshop
Jan
25

Animal Kindness Workshop

The Gloucester-Mathews Humane Society is hosting an Animal Kindness Workshop on Thursday, January 25th from 1 to 3 PM in the GMHS Lobby. Drop by to help create toys and enrichment items for homeless pets. All materials will be provided, and the event is open to all ages. No registration is needed!

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The Lafayette Bicentennial & Gloucester County
Jan
12

The Lafayette Bicentennial & Gloucester County

Join Robert Kelly, Director of the Gloucester Museum of History, at the Gloucester Historic Courthouse (6504 Main Street) on Sunday, January 12th, from 2 to 3 PM for a discussion on General Lafayette’s legacy and his connections to Gloucester. Learn about the Lafayette Bicentennial and Stuart Wells Jackson, co-founder of the American Friends of Lafayette, who lived in Gloucester from 1944 to 1957.

This free and family-friendly event is open to all!

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Erik Gaines Music
Dec
19

Erik Gaines Music

Come for the craft beer, stay for the music. Erik will be strumming the night away with a setlist that'll have you singing along or just enjoying the vibes. It's the perfect pre-Christmas chill-out session!

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Gloucester Farmer's Market
Dec
14

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. Free family activities including family photos, as well as, holiday presentations by various community groups and choirs in the Historic Church.

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2024 Christmas and Holiday Parade
Dec
7

2024 Christmas and Holiday Parade

The 2024 Christmas & Holiday Parade on Main Street is a festive celebration to kick off the holiday season. Join us for an enchanting afternoon filled with lights, music, and creative floats as they make their way down Main Street. Stick around after the parade for the annual tree lighting, sponsored by the Cook Foundation & Gloucester Main Street Association.

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Arts On Main: A “Celebration of the Arts" Soirée
Nov
16

Arts On Main: A “Celebration of the Arts" Soirée

Join Arts on Main at our annual Fall Fundraiser! At this popular event, guests will enjoy the musical stylings of award-winning musician Professor Amy Insley as well as drinks and heavy hors d'oeuvres by Gidi Gourmet! Soirée attendees will also be able to participate in a live/silent auction to win trips, experiences, and art that will be on display at Arts on Main for the month of November.

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