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Ultimate Holiday Shopping Itinerary

Shoppers in winter fashion on a Long Island Main Street Shoppers in winter fashion on a Long Island Main Street

Ultimate Holiday Shopping Itinerary in 3 Days

For the ultimate holiday shopping trip, follow our three-day itinerary for a mix of seasonal eats, local small businesses you can support this holiday season and family-friendly activities to celebrate this time of year.

shop small
Shop Small

Day 1

This holiday season come together to support local businesses and contribute to our regional recovery efforts by participating in #ShopSmallLongIsland.
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Day 2

Blackstone Stakehouse

Blackstone Steakhouse

Our menu is truly unique, combining tantalizing steakhouse classics with amazing sushi and seafood creations. In addition to serving the finest prime dry-aged and Kobe beef, we have our own authentic sushi chef and a fabulous sushi and raw seafood bar.

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charles dickens festival

Charles Dickens Festival

Every December, the streets of Port Jefferson are lined with residents volunteering in Dickens-era costumes as Dickens-era characters and performing vignettes from the author’s prolific works. Every business and community organization gets involved in some way as they have for over 25 years.

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vanderbilt museum planetarium

Bright Lights at the Vanderbilt Museum

Every weekend through December 19th, the Vanderbilt Museum in Centerport is hosting a socially-distant, outdoor holiday festival on its beautifully decorated grounds. Experience holiday lights, themed displays, festive food, music, appearances by holiday characters, and more!

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Oheka Castle mansion on Long Island

Oheka Castle

A breathtakingly beautiful historic mansion located on the famed Gold Coast of Long Island between New York City and The Hamptons. At OHEKA CASTLE guests will discover a World of charming luxury and European ambiance. OHEKA is listed on the National Register of Historic Places.

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Day 3

shoppes at east wind

The Shoppes At East Wind

While visiting The Inn at East Wind, enjoy the fresh air as you take a walk over to the The Shoppes at East Wind, where you can stroll along the brick pathways and take a ride on the grand carousel. Explore the variety of local merchants from nostalgic candy to cheeses & olive oils and fine wine.

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Fireside lounge seating at Hotel Indigo on Long Island's North Shore

Bistro 72 at Hotel Indigo

Located in Hotel Indigo, Bistro 72 has received many awards for its delectable dishes. This casually elegant restaurant and lounge serves up contemporary dining full of flavor with the option to dine al fresco next to a fireplace.

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preston house and hotel

The Preston House and Hotel

Located minutes from the famed Hamptons on the South Fork and historic Wine Country on the North Fork of Long Island, The Preston House & Hotel is a beautifully reimagined hotel in downtown Riverhead. This 1905 historical home once owned by Henry H. Preston, the first salaried sheriff of Suffolk.

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holiday light show splish splash waterpark

Splish Splash Waterpark

Head to the Riverhead Light Show at Splish Splash Waterpark for drive-through holiday fun!

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Local Wine & Spirits

21+ Tip

Stop at RGNY or Baiting Hollow Farm Vineyard for local wines, Long Island Spirits or Montauk Distilling Co. for locally-distilled spirits, or North Fork Brewing Company for Long Island-made beer.