James Lane readers, I’m bringing you the ultimate guide to a magical holiday season! This time of year, the North Fork transforms into a winter wonderland filled with festive charm, cozy vineyard experiences, and delightful local shops. Whether you’re planning a family outing or a chic weekend escape, I’ve curated the best of the season just for you.
For the past 14 years, I’ve relished the holidays on the North Fork, sipping wine at my favorite vineyards, taking in quaint decor, and the unmistakable warmth of this idyllic region. Ready to elevate your holiday plans? Let’s dive into my top picks for an unforgettable North Fork holiday season!
Santa’s Christmas Tree Farm, Cutchogue
Nothing says holiday magic like Santa arriving in style — on a fire truck! On November 29, at 10 AM, Santa kicks off the season at this enchanting farm, where the festivities continue every weekend until Christmas.
From ice skating and bouncy castles to warm Dreesen’s donuts and hot cocoa, this is where holiday memories are made. Be sure to explore the Christmas shop, a treasure trove of themed trees and glittering décor.
For a touch of tradition, pick up a saw and cut down your own Fraser fir — it’s a charming family moment you’ll never forget.
RGNY Vineyard, Riverhead
For a cozy, luxurious experience, book the Winter Ride Through the Vines at RGNY. This horse-drawn carriage ride pairs the stunning vineyard scenery with the tradition of warm Mexican hot chocolate.
After your ride, unwind in the tasting room with a wine flight and their decadent RG|MX cheeseboard. I took my little ones, and let me tell you — the joy in their eyes (and mine!) was unforgettable. It’s festive, refined, and oh-so Instagramable.
LUMBER + Salt, Jamesport
If unique gifts and vintage charm are on your holiday list, LUMBER + Salt is a must-visit. This beautifully curated antique shop offers treasures you won’t find anywhere else, from repurposed goods to one-of-a-kind décor.
And don’t miss their darling coffee shop — it’s the perfect spot to recharge with a latte before a day of exploring the North Fork. Wait until you see the whole place dolled up for the season!
The Chalet At Macari Vineyards, Mattituck
The Chalet at Macari is pure winter perfection. Beginning December 6, this Alpine-inspired tasting room offers fireside indulgence with library wines, Roberta’s pizza, and artisanal cheese boards.
The highlight? Their newly released LUCIANO III red blend — a luxurious bottle that’s as complex as it is divine. Whether you’re cozying up with a date or celebrating with friends, The Chalet is an absolute holiday must.
Southold General, Southold
Treat yourself to a little slice of Paris this holiday season with Southold General’s very French Christmas. Chef François Payard has crafted exquisite bûche de Noël offerings in dark and milk chocolate—each as decadent as it sounds.
Pair their sweet delights with an expertly brewed coffee, and you have the ultimate holiday indulgence. Southold General is also brimming with festive surprises, making it your one-stop shop for all things merry and bright. Make Southold General your first stop on the Southold Holiday Stroll scheduled for Friday, December 6, from 5 to 8 PM. You’ll want a seasonal latte in hand as you shop at local favorites like touchGoods, Arnie Paperie, White Flower Garden, White Flower Farmhouse, and more!
Whether you’re cutting down a Christmas tree, sipping wine by a roaring fire, or uncovering unique treasures, the North Fork offers a holiday experience like no other. Embrace the charm, savor the indulgences, and make this season truly unforgettable.
Enjoy the magic of the season on the North Fork!
Kelly’s North Fork Gift Guide
