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.

Raise a stein and celebrate Oktoberfest with Gloucester Brewing Company! Their anticipated Fairfield Fest, a German-style Festbier, will be on tap, while Dominion Dogs will be serving a German-inspired menu all day long.

The Gloucester Wine Festival, hosted by the Gloucester County Chamber of Commerce at Brent & Becky’s, is your passport to the best of Virginia wine, food, and music. 

Stop by Main Street on Sept 20 to enjoy live music and support the fight against cancer!

This free concert will feature multiple bands performing, and donations will be set up for fundraising for the Brush Away Cancer Society.

Join Camp Cardinal RV Resort for the September 2025 edition of Virginia Wine Camp featuring an intimate guided tasting hosted by Meadmaker (and founder and owner) Glenn Lavender of Silver Hand Meadery.

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.

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).