Gloucester Main Street Organizations work together to transform our Main Street for the 21st century while preserving our history.
Don’t Miss these Events on Main Street in June!
June 6th - Brews, Brine & Wine
June 7th - Paint Main
June 7th - Symphony Under the Stars
June 14th - Plein Air Gala
June 21st - York & Main Art Show
June 28th - Art in the Village
June 28th - It’s a Wrap Reception
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.
-
![]()
Daffodil Festival attendees had fun making their mark on Main Street!
-
![]()
Beer "Gardeners" having fun at the Daffodil festival!
-
![]()
Don't miss watching the Pro's paint with our local community painters during Paint Main on June 7th!
-
![]()
Oysters, Beer, Wine, Whiskey and Art...what more could you want at Brews, Brine & Wine coming on June 6th?
-
![]()
The RaJazz band is back by popular demand at Brews, Brine & Wine held at the Timberneck House in Machicomico!
-
![]()
Shout out to Split Enz for sponsoring the Kid's Zone at the Daffodil Festival!
-
![]()
Summer Festivals are coming our way:) Check out our events page to find out all the latest!
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!
