On Friday, October 31, 2025, Main Street retailers welcomed many tricks or treaters. There were Skeltons, Minnie Mouse, Frank Sinatra, the Scream, princesses, cows, Darth Vader, the Rumbles from the Flintstones and many more. Thank you all who came out to enjoy the generosity of Gloucester’s Main Street.
Tag: Main Street
Smiles in Gloucester on HALLOWEEN

Smiles in Gloucester – 25122

Smiles in Gloucester – 25115

Smiles in Gloucester – 25030 at Happy Tails Shoppe


Happy Tails Shoppe at 186 Main Street Gloucester Mass
Smiles in Gloucester – 25023

Smiles in Gloucester – 25013

Smiles in Gloucester – 25004


GLOUCESTER SMILES – 24077

GLOUCESTER SMILES – 24044

ENJOY BOBA TEA at 206 Main Street


From Wikipedia, the free encyclopedia
Bubble tea (also known as pearl milk tea, bubble milk tea, tapioca milk tea, boba tea, or boba; Chinese: 珍珠奶茶; pinyin: zhēnzhū nǎichá, 波霸奶茶; bōbà nǎichá) is a tea-based drink that originated in Taiwan in the early 1980s.[1][2] Taiwanese immigrants brought it to the United States in the 1990s, initially in California through regions including Los Angeles County,[3] but the drink has also spread to other sates and countries.
ENJOY Gloucester !
Fun Holiday events on Main Street
Thank you, Patty Gates from the Cape Ann Olive Oil Store. Please shop local


Dressing up? Check out Pink ‘Barbie’ at Bananas! #GloucesterMA
What to wear? Bananas Gloucester has options. Barbie is a regular there.







Bananas. 78 Main St. Gloucester, MA (978) 283-8806


What’s Happening at I4 C2? #GloucesterMA
Jan. 10, 2023.
Before spring, DPW is managing a gas work project on Main Street between Duncan and Hancock Streets.
A temporary staging site has been set up on I4,C2 (65 Rogers St). Street signs alert drivers on Main. This job is by National Grid that has a subcontractor, Neuco.
Public Works is heavily involved in all aspects of any utility work in the city and “stays tight with projects every step of the way.”




Today is Gloucester’s 49th Annual Ladies Night 2022!
Dec. 1, 2022 All day!
The wreaths are up on Main Street, the Lobster Trap Tree is beckoning and charming in its Before state, the shops and restaurants adorned and merry, and today’s weather is clear and crisp for Gloucester’s 49th annual “Ladies Night”! What are the store specials and holiday treats that will tempt us tonight?



photos: Sunrise – Main Street, Gloucester, Mass. ready for Ladies Night
For years my mother and I met up at Halibut Point Restaurant on the East End for a festive toast before strolling and shopping Main Street. I think I had my first buttered rum there. We had so many favorite stops. What Ladies Night traditions do you recall fondly?
**Which means: the 50th Ladies Night will land in Gloucester’s 400th+ Anniversary year!**
Gloucester Smiles – 2001



Gloucester Smiles – 1999




Gloucester Smiles – 1989



Sunflowers and Ukraine Flags | Main Street Storefronts, Downtown #GloucesterMA







March 2022 – POP GALLERY, Design of Mine, Stage Fort Park, City Hall, Our Lady of Good Voyage, Washington Street
Blue skies and blanketed 2 | Stage Fort Park, Backshore- after January 29th winter storm #GloucesterMA
stunning winter morning, February 1, 2022, about 7:30 am. Gloucester, Ma.
incl. snapshot motifs: backshore, Centennial & Stacy Boulevard, Stage Fort park, Good Harbor Beach












Jan. 31, 2022 – open with sidewalks and snowbank cuts ready for customers


















