Kelly Siry’s North Fork Holiday Guide

Everything you love about the North Fork of Long Island is magnified around the holidays! Picture serene stretches of farmland dotted with twinkle lights and vineyards blanketed in snow. Natural wreaths hang on doors and happy shoppers peruse local shops for the perfect gift. For over 10 years, my family and I have enjoyed all the seasons that the North Fork has to offer. I’ve come to love the uniqueness of experiencing the holidays here and you will too.

Here are my top picks for things to do this holiday season on the North Fork:

Visit Santa’s Christmas Tree Farm.

Located in Cutchogue, this Christmas-centric destination comes alive at this time of year. They boast a shop brimming with trees and ornaments, a full-scale Christmas town, and plenty of gifty items. Although it is his busiest season, Santa graces the farm every weekend through Christmas, happily posing for free photos with families. You may even spot the Grinch lurking around. Children can enjoy ice skating, Christmas-themed bouncy castles and more. And of course, you can purchase your Christmas tree at the farm! You may choose to cut your own or pick from a pre-cut selection of Douglas Firs.

Rose Andrews at Andrews Family Farm

Get crafty with a holiday wreath workshop at Andrews Family Farm in Calverton.

Andrews Family Farm is my favorite farm to visit for festive poinsettia, garlands, and wreaths. Their variety of poinsettia draws holiday décor enthusiasts from near and far to find the perfect shade.

Create holiday treats made entirely of gourmet chocolate at one of Disset’s chocolate workshops.

Everyone loves something sweet around the holidays and creating a fun chocolate art piece yourself makes it that much sweeter. You can participate in workshops like painting your own chocolate canvas and building your own chocolate house. A workshop at Disset in Cutchogue is a fun holiday activity and makes a fantastic gift.

Attend a barrel tree lighting at Lenz Winery in Peconic.

Sip a glass of Cabernet Sauvignon as you watch the lights illuminate the massive tree constructed completely out of wine barrels.

Take a trip to The Chequit on Shelter Island.

The 150-year-old hotel’s wrap-around porch is festively adorned with twinkling garland and wreaths. This year they will host a slew of holiday-themed events like brunch with Santa on December 10 and an Ugly Holiday Sweater Party on December 17.

Indulge in something sweet.

Our favorite mobile treat truck, The Treatery, has opened a brick-and-mortar shop in Jamesport which means soft, gooey chocolate chip cookies and creamy loaded hot cocoa are now readily available this holiday season.

Compose a holiday centerpiece while enjoying a farm-to-table brunch in Riverhead.

Hosted by the succulent queen, Imaginariums by Elissa, at the North Fork’s only culinary farm, 1760 Homestead Farm. On December 10 you can create a long-lasting holiday centerpiece with succulents and while you are there, peruse their historic barn filled with holiday gifts and décor.

Dream of a white Christmas.

The Dimon Estate goes all out when decking the halls of the manor for the holidays. Join The Dimon Estate, a historic manor and restaurant located in Jamesport as they partner with Bedell Cellars, Corey Creek Taproom to present a wine dinner to celebrate the iconic white Christmas.

Enjoy tabletop s’mores and port at North Fork Table & Inn in Southold.

This experience is made for two and features housemade graham crackers, marshmallows, and Aleppo-chocolate bark. You also have your choice of port or Valrhona hot chocolate.

Enjoy a holiday cocktail flight at Montauk Distilling Co. in Riverhead.

This boutique distillery makes all of its spirits on premises. They create unique seasonal cocktails that always get me in the mood for the holidays.

Ring in 2023 with an opulent New Year’s Eve party at The Soundview Hotel in Greenport.

I have attended a number of parties at The Soundview, and they have never failed in their epic themed cocktails. There is no better way to start the New Year than with a terrific drink in hand and a sensational party atmosphere.


North Fork Holiday Gift Guide By Kelly Siry

Kelly Siry


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