atercolor painting of downtown Gloucester, Massachusetts in winter. A festive Christmas tree made from stacked lobster traps stands decorated with lights and a golden star, placed in front of the historic red police station. Snow covers the sidewalks and roofs, while wreaths and holiday decorations brighten storefronts and homes. Cars are parked along the street, capturing the charm of Gloucester’s holiday season.

Gloucester, MA : Fall & Winter Highlights (Oct 2025 – Feb 2026)

Buyer & Seller Tips| North Shore Coastal Living| Things to Do on the North Shore| New England History
October 01, 2025•0 min read
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Gloucester MA eventsNorth Shore MA Real EstateFall Festivals GloucesterWinter Activities Cape AnnCape Ann Plein AirCape Ann MuseumGloucester Stage CompanyMiddle Street WalkLobster Trap TreeCape Ann Winter birdingKathleen Militello RealtorEssex County Homes for SaleMoving to Gloucester
Kathleen Militello has been helping clients since 2007, serving first-time homeowners, downsizers, and move-up buyers across the North Shore of Boston and Essex County, Massachusetts, including Ipswich, Beverly, Gloucester, Rockport, Essex, Manchester-by-the-Sea, Salisbury, Salem, and Lynn. Her clients value personalized guidance, advanced AI-powered tools, and deep local expertise to make confident real estate decisions when buying or selling along the Massachusetts coast.

Kathleen Militello

Kathleen Militello has been helping clients since 2007, serving first-time homeowners, downsizers, and move-up buyers across the North Shore of Boston and Essex County, Massachusetts, including Ipswich, Beverly, Gloucester, Rockport, Essex, Manchester-by-the-Sea, Salisbury, Salem, and Lynn. Her clients value personalized guidance, advanced AI-powered tools, and deep local expertise to make confident real estate decisions when buying or selling along the Massachusetts coast.

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