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.

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!

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!

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!

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!

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!

Celebrate the magic of the season at Gloucester Main Street’s Holiday Open House on Sunday, December 8th!

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.

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.

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!

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.

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!

Join Renate Bumgarner at Arts on Main every Thursday from 12:30 PM - 3:30 PM for an Oil Painting Class!

Come see the Dave Keller Band live at Flat Iron Crossroads, November 9th at 5:30 pm!

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.

Join Ethan Brown at Arts on Main on Saturday, November 9th from 1:00 PM - 4:00 PM for a Native Gourd Workshop!

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!

Join Renate Bumgarner at Arts on Main every Thursday from 12:30 PM - 3:30 PM for an Oil Painting Class!

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.

Come see Mean Mary & The Contrarys live at Flat Iron Crossroads, October 19th at 6:30 pm!

Beggars Banquet is the premier Rolling Stones Tribute Band of the Carolinas—come catch them at Flat Iron Crossroads October 12th!

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 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.

Performing at the Blues Fest in Gloucester, VA on Saturday, 10/5 is The Nighthawks with Bob Margolin, BluzHammer, and Kurt Crandall & True Story!

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!