Upcoming Events
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!
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!
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!
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.
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!
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.
Amazing Grace Flower Farm
Amazing Grace Flower Farm invites you to a delightful Sunday afternoon of fun, fellowship, and floral creativity! Learn how to design your own unique bouquet using locally grown flowers, guided by the farm’s owner, Varetta Hamlin. The workshop will take place at the York & Main Art Gallery on Sunday, October 27, from 2 - 4 PM.
Blues Fest at Flat Iron Crossroads
Performing at the Blues Fest in Gloucester, VA on Saturday, 10/5 is The Nighthawks with Bob Margolin, BluzHammer, and Kurt Crandall & True Story!
Oktoberfest
Join Riverside's Sanders for their first annual Oktoberfest on October 5th, from 10 AM to 5 PM! Enjoy a day filled with fantastic food, unique vendors, and much more. Gloucester Brewing Company will be serving their finest local beers, and various local vendors will showcase their handmade creations. Best of all, entry is free!
Sanders’ First Annual Oktoberfest
The Gloucester Main Street Association is proud to sponsor Riverside's Sanders first annual Oktoberfest! Join Sanders this Saturday, October 5th, from 10 AM to 5 PM, for a day filled with fantastic food, unique vendors, and much more.
Live Music at Gloucester Brewing Company - Ben Long
Ben Long joins Gloucester Brew Co. for live music!
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!
Beaded Pumpkin Workshop with Dia Lawless
Are you ready for fall? Make the first fall decoration of the season for your home! You will learn how to use metal, beads, wire, and ribbon to create a unique beaded pumpkin. This lovely beaded pumpkin is fun, festive, and easy to make! Leave with something you are proud to display and tell people you made. Come enjoy an evening that will bring in the season!
Corey Arceneaux and the Zydeco Hot Peppers
Corey Arceneaux and the Zydeco Hot Peppers are at Flat Iron Crossroads on September 21st!
Wine, Whiskey, and WhatNot Festival
Get ready to indulge your senses at this year’s Gloucester Wine, Whiskey, and WhatNot Festival on September 21st! This year, the Gloucester County Chamber of Commerce has turned up the excitement by adding whiskey tastings into the mix. Your ticket includes wine and whiskey tastings, plus incredible music by The Deloreans 80's Band.
Live Music at Gloucester Brewing Company - Edward Wade
Edward Wade joins us for live music this week! He’ll be playing at GBC from 6 to 9 pm, don’t miss it! Meanwhile, Nomads will provide the meals with their food trucks!