Port Jefferson is turning into a holiday wonderland this season

Port Jefferson is about to glow.

The village is rolling out a full slate of celebrations beginning Nov. 21, when the Pink Friday Boutique Crawl officially kicks off the holiday season. From Thanksgiving through Christmas, downtown shops, restaurants, salons, and cafés will come together to transform Port Jeff into what organizers are calling a “magical holiday wonderland.”

Visitors can expect lights, music, themed nights, and a steady run of festive pop-ups — all designed to support small businesses and bring families into the village throughout the season.

“This is one of our favorite times of year,” said a spokesperson for the Port Jefferson Retailers Association. “Our businesses are working together to make Port Jefferson glow with holiday spirit. We invite everyone to come stroll our streets, shop local, dine, and enjoy all the magic our village has to offer.”

What to expect in Port Jeff this holiday season

Merchants across the Village of Port Jefferson are teaming up to offer weeks of special programming, including:

• Photos with Santa
• Luminary shopping evenings
• Historic house tours
• Special holiday restaurant menus
• A reindeer scavenger hunt for families
• First responder appreciation night
• Pop-up tree farm and festive displays
• Holiday treats from local bakeries and cafés
• Unique local gift-shopping experiences
• And more surprises each weekend

The kickoff: Pink Friday Boutique Crawl

Pink Friday Boutique Crawl
Nov. 21, 2025

A village-wide night to shop, sip, stroll, and enjoy exclusive promotions from participating boutiques.

The event is part of a nationwide movement focused on supporting small retailers ahead of Black Friday. In Port Jeff, it marks the official start of the village’s holiday programming.

Organizers encourage visitors to follow @portjefftogether for the full calendar as events are added throughout the season.

More fun

Dickens Festival returns to Port Jefferson bigger than ever this December