Long Island's Most Unusual and Underrated Christmas and Holiday Events

Explore the Victorian era during Port Jefferson's Charles Dickens Festival. Photo courtesy of the festival's Facebook page

Looking for something out of the ordinary to add to your list of holiday must-dos? Long Island is full of traditional holiday fare like light shows and decorated neighborhoods, but maybe you're looking for something a bit more off the beaten path. If so, we've rounded up Long Island's most unusual and underrated holiday events that Long Island families won't want to miss. 

Take a look at our Guide to Holiday and Christmas to get the most out of this holiday season.

NYC's Most Unusual Christmas Events

Hundreds of tuba players converge on Rockefeller Center each December for a merry afternoon of carol playing. Photo courtesy of Tishman Speyer

Christmas in NYC brings to mind the Rockefeller Center Christmas tree, the Rockettes, ice skating in Bryant Park, and dazzling storefronts on Fifth Avenue. While we love these classic and time-honored NYC holiday attractions, there are also many lesser-known and more offbeat NYC holiday activities that are just as delightful and often come with smaller crowds.

So, while you should definitely go see Santa at Macy's or the Holiday Train Show at the NYBG, be sure to save space in your holiday schedule for one of these underrated holiday activities in NYC. Below, we're highlighting underrated and unusual holiday activities that are smaller in scale, artist-driven, a little quirky, and uniquely New York.

You'll find all of our holiday picks for the best family-friendly activities in our Ultimate Guide to Holiday and Christmas Events in NYC for Families. Find more insider tips on how to spend the Christmas season in New York in our ultimate 3-day itinerary for a magical NYC holiday with kids.

Ultimate Winter Bucket List: 40 Best Things to Do with Kids in Philly

 A winter oasis, Blue Cross RiverRink Winterfest houses a skating rink overlooking the Delaware River, a ski chalet-style lodge and more. Photo by Danielle Smith

Winter can test your creativity in entertaining the kids, and sometimes you just need to get out of the house or at least find new indoor activities. Fortunately, we have some amazing outdoor winter activities that allow kids to romp, play, and explore, as well as fresh ideas for being at home that can shake off winter fatigue.

For all the best ways to make the most of the chilly temps, check out the Best Outdoor Ice Skating, and don't miss our Winter Activities Guide. Looking for ways to stay entertained at home? Check out our Boredom Busters Guide for lots of great ideas!

Disneyland Just Announced a HUGE Bluey Surprise—and Your Kids Will Lose Their Minds

Artist concept of the Bluey show coming to Disneyland. Photo courtesy of Disney and Ludo Studios

Bluey-loving families, get ready—because Bluey, Bandit, Bingo and crew are coming to Disneyland Resort! The park has just announced an all-new, fully immersive Bluey celebration, will bring everyone’s favorite heelers to life at the Fantasyland Theatre beginning March 22, 2026.

Kids can finally meet Bluey and Bingo in person, dance along, and step into their playful world for the very first time at Disneyland. If your family has watched every episode on repeat, this is your call to start booking your 2026 vacation (or Bluey fan's birthday celebration?) right now.

But wait, there's more...

Free TDF Memberships Means Cheap Broadway Tickets for Class of 2026

Kick off the 2026 graduation celebrations early by having your teen sign up for a FREE TDF membership and a chance to see CATS: The Jellicle Ball next May. Photo courtesy of the production

If you've got a high school senior who is into the arts, listen up: TDF, the not-for-profit performing arts org, is offering FREE year-long TDF memberships to graduating high school seniors from NYC public and charter schools. So, if your kid can't wait to see everything from Broadway shows to off-Broadway performances, dance, and more—all at deeply discounted prices—read on for details on how the Class of 2026 can score this special gift.

Don’t Miss Holiday Circus Spectacular Merry Mayhem at the New Victory Theater

The New Victory Theater continues its 30th birthday celebrations this December with the high-energy holiday circus, Merry Mayhem.

If you’re looking for a high-energy holiday show that’ll have the whole family in stitches, Merry Mayhem is it! Jam-packed with acrobatics, pranks, live music, and side-splitting Aussie humor, Melbourne’s legendary Circus Oz is returning to the New Victory this December with a new riotous circus spectacular to help celebrate the theater’s big 30th Birthday Season.

From the free hands-on lobby activities to a special ticket deal, here’s everything parents need to know before heading to 42nd Street for this high-flying, holiday spectacle.

A Beloved Holiday Event Returns to the Dallas Design District

Christmas at the Anatole is a fun DFW holiday tradition! Photo by Seth Cullen

Ice skating, train rides, twinkle lights, oh my! ‘Tis the season for holiday fun, and one of Dallas’ most beloved hotels knows how to celebrate. Christmas at the Anatole has returned for 2025, and whether you’re a guest or want to enjoy the holiday activities, there’s room for you and your whole crew. I took my kids to the opening weekend, and we had a blast. Here's how to make the most of your visit to this holiday tradition in the Design District. 

The Most Unique Christmas Trees in NYC You’ll Want to See (and Snap!) this Holiday Season

The tunnel through the Christmas tree at 1221 Avenue of the Americas is a delightful surprise! Photo by Jody Mercier

New York City sparkles with Christmas trees on every corner, but some standouts go way beyond twinkling lights and classic ornaments. From dazzling museum creations to quirky neighborhood wonders, these are the most unique Christmas trees in NYC that families flock to each year. Each is as photogenic as it is imaginative.

Whether you’re hunting for an off-the-beaten-path Christmas tree in NYC, planning a festive family itinerary, or just looking to refresh your holiday photo roll, the city is packed with unexpected delights—think intricate origami, vintage toys, and even construction cones turned into holiday magic. Read on for the most creative, must-see NYC Christmas trees that make the season shine a little brighter.

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