Ultimate Holiday Shopping Itinerary

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.

Day 1

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

  • Jones Beach State Park

Magic of Lights is a dazzling, drive-through holiday lights experience featuring favorite holiday scenes and characters of the season using the latest LED technology and digital animations. Experience Magic of Lights from the comfort and safety of your own car as you wind through the sparkling path…

  • 1080 Corporate drive
  • (516) 693-5400

City Celler is defining the exciting new cuisine known as American Modern. Our take on this breaking new culinary development is diverse, ranging from fresh approaches to everything from comfort food to gourmet dishes, with surprising combinations of tastes, textures and colors. Steaks and fresh…

Day 2

  • 10 Pinelawn Road
  • (631) 271-7780

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. Plus, our sommelier can help you select the…

  • 117 North New York Avenue
  • (631) 385-1515

Dedicated to the expression of modern American cuisine, Prime is more than just a culinary adventure, it is a true experience. Guests can choose from an array of raw bar favorites, like blue point oysters, little neck clams, and lobster cocktail, along with Mizu Sushi, and steaks and chops like…

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.

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! Tickets can be…

  • 135 West Gate Drive
  • (631) 659-1400

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 and a member of…

Day 3

  • 5768 Route 25A
  • (631) 929-3500

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, fine wine to…

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.

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. Check the website for details on live entertainment.

Fun for the Whole Family

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

  • 428 E Main St
  • (631) 775-1500

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…