A light blue building with white columns and stripes, resembling a classical temple, next to a bright blue building with a sign that reads "Lulu Birds Kitchen". There are trees, a street lamp, and parked cars in front.
Man in orange checkered shirt, bucket hat, and glasses sitting on a park bench reading a paper on a sunny day in a small town.
Gloucester Brewing Company
Fresh Produce at Ware Neck on Main Street
Three friends standing on sidewalk next to a mural of yellow and white flowers with pink accents on a blue brick wall, smiling and talking, holding brown paper bags.
Inside a cozy restaurant with wooden floors and ceiling, with a large window showing a green outdoor view. There are white chairs and tables set for guests, some with small plants. On the right, several beer taps with branded handles are visible.
Logo for Main Street Preservation Trust featuring colorful storefronts and buildings inside a house-shaped outline.

Gloucester Main Street Organizations work together to transform our Main Street for the 21st century while preserving our history.

Logo of Main Street Gloucester featuring a blue street lamp inside a circular blue background with the words 'Main Street' and 'Gloucester Main Street' underneath.
Fashion boutique display with a mannequin wearing a leopard print sleeveless top, a white handbag, jewelry, and small leather accessories.
Two people looking at a smartphone through a public metal art sculpture, with a mural and parked cars in the background.
Person holding a black slate serving platter with assorted cheeses, green olives, figs, sliced melon, honey in a jar, and red chili peppers.

A modern take on the classic American downtown. Shop, eat, drink, stroll, laugh, taste, toast, dance, talk, and meet up. On the very Main Street where that’s all been happening for over 300 years.

Graphic with the text 'Meet Us on Main Street' and an outline of a shopping district with buildings, labeled 'Gloucester, VA'.
  • A couple standing in front of a large banner that reads "Virginia is for Main Street Lovers." The banner is decorated with colorful handprints and signatures. The couple is smiling and posing for the photo, with the trees and a brick house in the background.

    Daffodil Festival attendees had fun making their mark on Main Street!

  • A group of eight people standing outdoors in front of a red food truck, holding yellow cups and smiling at the camera.

    Beer "Gardeners" having fun at the Daffodil festival!

  • People painting outdoor on green grass under trees with a sidewalk and parked cars in the background.

    Don't miss watching the Pro's paint with our local community painters during Paint Main on June 7th!

  • Person shucking oysters on a red table outdoors with a truck and green fields in the background

    Oysters, Beer, Wine, Whiskey and Art...what more could you want at Brews, Brine & Wine coming on June 6th?

  • Outdoor music band performing under tents at an arts festival in front of a weathered, two-story house.

    The RaJazz band is back by popular demand at Brews, Brine & Wine held at the Timberneck House in Machicomico!

  • Two people wearing yellow shirts sitting on chairs outdoors in front of an inflatable bounce house, with a sign for 'Speak Easy Salon' nearby.

    Shout out to Split Enz for sponsoring the Kid's Zone at the Daffodil Festival!

  • People gathered at an outdoor event under tents, with one person serving food or drinks at a booth, and others socializing on a grassy area.

    Summer Festivals are coming our way:) Check out our events page to find out all the latest!

Colorful watercolor splash with the text "What's Happening?" in a handwritten style.

Want to know what’s going on in Gloucester? You can find amazing events all year long on Main Street. Explore everything that’s going on, from annual festivals and holiday celebrations to concerts and treasure hunts and so much more! Discover the best things to do by checking our calendar regularly!