Stop by the Fine Arts Museum of Gloucester for a powerful conversation with filmmaker and director Laura Seltzer-Duny as she shares behind-the-scenes insights from her upcoming documentary. 

Learn about her journey bringing together black and white descendants, visiting the historic Brooks Cemetery in Mathews, and uncovering the untold story of the first Contraband families.

The event will feature a screening of the trailer and selected clips, offering a glimpse into the lives of the formerly enslaved Africans who sought refuge behind Union lines during the Civil War—and the resilient community they built in Hampton, Virginia.

For more information and to RSVP, email: sara@fairfieldfoundation.org

Source: https://visitgloucesterva.org/tourism/events/the-gate-the-story-of-americas-first-contraband-community

Stop by The Nook and decorate your own mini bookshelf with Printed Plot Co. 

Wear your most favorite UGLY CHRISTMAS SWEATER and join together in beer and song as Erik Gaines leads patrons in a Beer & Carols celebration from 6:00-7:00 PM.

Join the Gloucester-Mathews Humane Society for a festive Kids Movie Night on Friday, December 19, from 5:30–8:00 PM! 

Grab your girlfriends and join The Silver Box for a fabulous night of fun, fashion, and exclusive perks.

Join The Fairfield Foundation for their second holiday open house and step back into the early 20th century as Fanny Catlett Montague’s reflections on Christmas in the Timberneck home are shared.

Join the fun on Saturday, December 13th, from 10 a.m. to 3 p.m. at the Gloucester Farmers Market on the beautiful historic grounds of Ware Church

Step into the warmth and charm of the season as Gloucester opens the doors to some of its most treasured historic sites. The Historic Holiday Open House offers a festive evening filled with holiday cheer, community spirit, and a celebration of the region’s rich heritage.

Join the Gloucester Museum of History for a special evening at the museum as they extend their hours for a festive holiday experience!

Get ready for a full day of holiday cheer in Gloucester Village!

The Christmas & Holiday Parade, presented by Gloucester Parks, Recreation & Tourism, kicks off at 3:00 PM with festive floats, marching bands, and holiday magic filling Main Street. 

Join the Gloucester Resource Council on Main Street as it is turned into a holiday wonderland full of joy, kindness, and holiday cheer. With your help, they will raise awareness and support for the many nonprofits, businesses, and government organizations that help make our community great.

Celebrate the season on Gloucester Main Street during the Holiday Open House on Saturday, December 6!

Enjoy photos with Santa, family-friendly activities like the Gratitude Tree and Letters to Santa, and shop local treasures. Festivities continue with the Gloucester Resource Council’s Festival of Trees and Common Ground, the Christmas & Holiday Parade presented by Gloucester Parks, Rec, & Tourism, and the Cook Foundation’s annual Tree Lighting.

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.

Join the Fairfield Foundation for the 5th ANNUAL Timberneck Turkey Trot 5k Run/Walk Fundraiser.

Run or walk this scenic, flat, paved 3.1-mile loop course at Machicomoco State Park in Gloucester, Virginia. Water will be available at the start/finish line, as well as at the halfway point of the race route. Public restrooms will also be available near the race finish.

Join Kelsick Market for an evening of fall flavors, live music, and community fun in the heart of Gloucester. 

Celebrate Halloween on Main Street in Gloucester on Friday, October 31, from 5–7 PM. Families are invited to enjoy safe trick-or-treating, candy, and festive fun. Our popular Costume Contest will return for its second year, thanks to Chesapeake Bank. Trick or Treat is made possible with support from the Gloucester County Sheriff’s Office.

Join the Gloucester Museum of History for the unveiling and dedication of its newly completed second-floor exhibit.

Visit Gloucester’s Secondhand Saturdays Are Back This October!

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.

Join the fun at GBC’s Howl-O-Ween Pawty! Dress your pet in their spookiest Halloween outfit for a chance to be crowned the contest winner.

Celebrate Halloween at the Gloucester-Mathews Humane Society with an afternoon of family fun!

Visit Gloucester’s Secondhand Saturdays Are Back This October!

Visit Gloucester’s Secondhand Saturdays Are Back This October!

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.

Visit Gloucester’s Secondhand Saturdays Are Back This October!

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.