Nassau County, Long Island’s Most Charming Holiday Towns

Take a stroll in the Hallmark Channel-like downtowns of some of Nassau County’s most charming towns. From ice skating to tree lighting to holiday shopping, there is plenty to do during the holidays in these quintessentially festive ‘burbs.

This quaint township pulls out all the merriment for the holiday season. The festivities kick off on November 29 with the town’s Holiday Magic on Small Business Saturday event, where local stores will be offering specials, Santa will ride a fire truck, Radio PW will be playing holiday music, singing toy soldiers and carolers will stroll the streets, and a free trolley will be available for shoppers. The festivities continue on December 6 for another Small Business Saturday with many of the same offerings. Additional festivities include a town tree lighting ceremony on December 7, concerts and performances by Cherish the Ladies, the Glen Miller Orchestra, and more, as well as plenty of discounts and promotions from local businesses.

Massapequa pulls out all the stops for the holiday season. Enjoy a winter wonderland out on the ice at Marjorie R. Post Community Park Ice Rink. December 6 marks the town’s annual Christmas Tree and Menorah Lighting Ceremony kicking off at 5pm, where guests can enjoy entertainment, music, hot chocolate, and of course, a visit from Santa. Locals can also register for Massapequa Chamber’s Holiday Party on December 11, located at Mercato Kitchen & Cocktails for music, food, and drinks. For family-friendly fun, stop by the Holiday Open House on December 13.

Home to Long Island’s number one Christmas attraction – Christmas House – Oyster Bay opens the immersive experience up for business on November 28 at Broadway Commons. On December 6, locals and visitors can stop by the town’s Holiday Market and Stroll, where there will be plenty of food, shopping, and festive music and a visit from Santa. If you’re looking to burn off all those Christmas cookies, join famous Theodore Roosevelt re-enactor Joe Wiegand on December 5 for a “Strenuous Life Hike” of the grounds of Theodore Roosevelt’s home, Sagamore Hill.

Mineola is bringing yuletide greetings to visitors during the holidays this year. The festivities begin on December 5 with the town’s Annual Tree Lighting and are followed by the Village Holiday Market on the first two weekends in December, which features food and drinks, fun activities, ice skating, music and entertainment, and character meet and greets. Kids can meet Santa, there will be a heated tent and a vendor village for shopping, plus many exciting performances.

With six neighborhood parks and a friendly neighborhood vibe, Garden City makes for the quintessential holiday town full of merriment and joy. The Village and Chamber of Commerce will hold the annual Christmas Tree Lighting and Hanukkah Festival of Lights on Sunday, December 7, beginning at 3:30 p.m. Enjoy holiday music, performances by Broadway Bund Dancers, The Garden City High School Vocal Jazz Ensemble, hot chocolate and a visit from Santa himself! Be sure to also visit the Garden City Hotel which caters to both children and adults with its holiday programming. Partake in Breakfast with Santa on December 13, the Grinchmas Saturday Afternoon Tea on December 20, or Christmas Eve and Christmas Day Dinner at the award-winning hotel.