Upcoming Events
Gloucester’s Secondhand Saturdays
Whether you’re a longtime fan of thrifting or a curious newcomer, there’s no better time to discover the treasures waiting for you in Gloucester County.
Beer Garden on Main Street - Locals Night
A weekend of family-friendly activities, including a dedicated kids’ zone, live music, craft beers, and food trucks!
Historic Garden Week in Gloucester 20225
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
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.
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!
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!
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!
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.
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!
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.
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.
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!
Galentine's Event at Mariposa Medical Spa
The gals at Mariposa will have Glow and Go treatments, Lip and Peel treatments, build your own mini bouquets, wine and more! Scentsy too!
Bread, Beer & Vinyl Fundraiser
Thursday the 13th, join GBC and Small Town Burger for Bread, Beers, & Vinyl Fundraiser at Gloucester Brewing Company benefiting the Bread For Life Community PANTRY, bring your fav vinyl for us to spin!
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.
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!
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!
Silenced Voices: Film Screening and Panel Discussion
The Fairfield Foundation Family Circle, a volunteer-led affiliate of Coming to the Table, is sponsoring “Silenced Voices,” a documentary honoring the legacy of African American communities!
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!
Edward Wade Music
Wind down after the holidays with a good beer and live music with Edward Wade at the Gloucester Brewing Company.
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!
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.
Robbie Kerns Music
They’re back at Gloucester Brewing Company Thursday, December 12, 2024 from 6-9 pm!
Come join us for good beer, good food, and good company!
Holiday Open House
Celebrate the magic of the season at Gloucester Main Street’s Holiday Open House on Sunday, December 8th!
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.
Small Business Saturday
Save the date! This Small Business Saturday, November 30th, join us on Gloucester Main Street to support the local businesses that make our town feel like home.
Live Music at Gloucester Brewing Company - Joe Heilman
Robbie Kerns joins us for live music this week! He’ll be playing at GBC from 6 to 9 pm, don’t miss it! Meanwhile, Coastal Thirst will provide the meals with their food trucks!
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.
Live Music at Gloucester Brewing Company - Robbie Kerns
Robbie Kerns joins us for live music this week! He’ll be playing at GBC from 6 to 9 pm, don’t miss it! Meanwhile, Coastal Thirst will provide the meals with their food trucks!
Arts On Main: Oil Painting Class
Join Renate Bumgarner at Arts on Main every Thursday from 12:30 PM - 3:30 PM for an Oil Painting Class!
Dave Keller Band at Flat Iron Crossroads
Come see the Dave Keller Band live at Flat Iron Crossroads, November 9th at 5:30 pm!
York & Main Grand (RE)Opening
York & Main is expanding! Ten local small business owners are joining the York & Main creative community. Please mark your calendar for our Grand (RE)Opening on Thursday, November 7th from 6-8 PM.
Arts On Main: Native Gourds
Join Ethan Brown at Arts on Main on Saturday, November 9th from 1:00 PM - 4:00 PM for a Native Gourd Workshop!
Arts On Main: Native Gourds (Copy)
Join Monti Sikes Wednesday, November 13th - Friday, November 15th from 12:00PM - 3:00PM at Arts on Main for an Oil and Cold Wax Workshop!
Arts On Main: Oil Painting Class
Join Renate Bumgarner at Arts on Main every Thursday from 12:30 PM - 3:30 PM for an Oil Painting Class!
Trick or Treat on Main Street
Join us on Main Street for this year’s Halloween Trick or Treat on Thursday, October 31st! From 5 to 7 PM, enjoy a safe, fun-filled evening with plenty of costumes and candy. Main Street will be closed during the event to ensure a safe environment for everyone.
Mean Mary & The Contrarys at Flat Iron Crossroads
Come see Mean Mary & The Contrarys live at Flat Iron Crossroads, October 19th at 6:30 pm!
Beggars Banquet at Flat Iron Crossroads
Beggars Banquet is the premier Rolling Stones Tribute Band of the Carolinas—come catch them at Flat Iron Crossroads October 12th!
The Fairfield Foundation's Historic House Party
The Fairfield Foundation hosts its 9th Annual Historic House Party at Exchange in Gloucester. Each year, Fairfield holds this exclusive event to celebrate the accomplishments of the year and raise funds for a new project. This June, the Richmond-based Cabell Foundation awarded Fairfield a $100,000 matching grant to restabilize the Rosewell Ruins. All money raised during the House Party will support this grant.