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1. Port Jefferson Village Annual Charles Dickens Festival – Port Jefferson

Why it's unusual or underrated: Go back in time to the Dickens era of the 1800s. Characters from the classic novel A Christmas Carol free roam the streets, such as Father Christmas, chimney sweeps, and, of course, Scrooge.
What visitors can expect: In addition to roaming characters, visitors will find lots of mostly free attractions (except for the ice skating, which has a fee). Free things to do include music performances, a capella choirs, magic shows, and Nutcracker performances. 
Event date: Saturday, December 6-Sunday, December 7, 2025, from 10am-7pm
Insider tips: Municipal lots can fill up quickly, so get there early to save yourself the headache of trying to find parking. 

2. Mr. Grump Pop-Up Bar Experience – Farmingdale

Why it's unusual or underrated: The Alibi Lounge transforms into Mount Crumpit, where visitors will get a meet and greet with the one and only mean green, the Grinch. 
What visitors can expect: Whimsical and who-sical decor decks out the space. Holiday-themed food and cocktails (and mocktails) are on the menu. Visitors will also get a themed souvenir cup to take home.
Event date: The event has multiple dates and times, running until Sunday, December 28, 2025. 
Insider tips: The reservation fee does not go toward the cost of food and drinks. Walk-ups are welcome, but reservations are highly recommended, especially for the family-friendly reservations. There is also an 18-and-over reservation. 

3. Jolly Grump Christmas Pop-Up Dining Experience – Patchogue

Why it's unusual or underrated: That Meetball Place offers Grinch-loving kids another opportunity to get close to the green grump. 
What visitors can expect: A performance by the Grinch, as well as a photo opportunity with the Grinch. Themed food and drinks will be available, but note that the reservation fee does not go toward the purchase of food and drink. All seatings are all ages. 
Event date: The event has multiple dates and times, running until Sunday, December 28, 2025. 
Insider tips: Reservations can be made here. Be sure to reserve standard table seating, as children will not be allowed at the bar. 

4. Annual Reenactment of the Flying Santa at Fire Island Lighthouse – Fire Island

Why it's unusual or underrated: Santa flies in a helicopter, need we say more? Yes, Santa himself makes landfall not in his sleigh, but in a helicopter.
What visitors can expect: A re-enactment of the 1953 event when a pilot, aka Santa, came to deliver presents to the lighthouse keeper and his family. Bring the camera for lots of great photo opportunities.
Event date: Saturday, December 13, 2025, from 11:30am-12:30pm. 
Insider tips: Get there early so you don't miss any of the excitement. 

5. Deep Sea Dreidels at Cold Spring Harbor Whaling Museum – Cold Spring Harbor

Why it's unusual or underrated: Decorate your own dreidel and carrying pouch, giving it a seaworthy flair. Explore the museum and learn about the history of games at sea. 
What visitors can expect: After decorating your dreidel, face off against others in an epic game of dreidel, gelt prizes included.
Event date: Sunday, December 7, 2025, from 11am-1pm.
Insider tips: There is an additional fee outside of admission to participate in the program. 

6. Nassau Lionel Model Train Open House – Levittown

Why it's unusual or underrated: The Nassau Lionel Operating Train Engineers only open the exhibit on select weekends throughout the year. There are festive additions to the model trains for a holiday feel.
What visitors can expect: This is home to Long Island's largest operating 3 rail O-Gauge train layout. 
Event date: Friday through Sunday, December 5-7, 2025, and December 12-14, 2025. Check the listing for exact times.
Insider tips: This is located in a basement and is not handicap accessible.

7. Celebrate Kwanzaa at Long Island Children's Museum – Garden City

Why it's unusual or underrated: Learn about the traditions and meaning of Kwanzaa. 
What visitors can expect: Children will learn about Kwanzaa and make crafts based on holiday traditions. They can create beaded ears of corn to represent members of their family and weave their own mkeka with paper.
Event date: Tuesday, December 30, 2025, from 1pm-3pm
Insider tips: This event is free with admission and recommended for kids ages 5 and up. 

8. Candlelight Evenings at the Old Bethpage Village Restoration – Old Bethpage

Why it's unusual or underrated: The 19th-century village at Old Bethpage Village Restoration is transformed by candlelight to celebrate the holiday season as it would be celebrated during the Civil War era. 
What visitors can expect: Carolers and brass quartets playing Civil War-era Christmas songs, a decorated 1866 tree, and stories of Christmas past. 
Event date: Friday-Tuesday, December 19-23, 2025, and Friday-Monday, December 26-29, 2025
Insider tips: Children under age 4 are free.

Check out the light show on the mini-golf course at Sayville Falls' Winter Garden.

9. Sayville Falls Winter Garden – Sayville

Why it's unusual or underrated: Unlike other Long Island light shows, this one occurs on an 18-hole miniature golf course. 
What visitors can expect: Thousands of holiday lights are strewn about the 18-hole miniature golf course with interactive displays and walk-throughs. For more information, check out our review about our visit to this unique holiday attraction.
Event date: The event runs until Monday, January 12, 2025. 
Insider tips: Make advance reservations if you'd like to spend some quality family time in the igloo. Reservations are $50 an hour.

10. Santa on the Farm Holiday Pajama Party and Santa on the Farm – Manorville

Why it's unusual or underrated: In juxtaposition to the mad rush of holiday shopping, the Long Island Game Farm invites families to take a breath, relax, and enjoy each other and all the holiday season has to offer.
What visitors can expect: At the pajama party, families can gather around the fire for songs and stories, have a gentle yoga session with Santa, and, of course, take photos with Santa. Families are encouraged to wear their pajamas, but it's not required. During the Santa on the Farm event, take a walk through the wooded trail, visit with animal ambassadors, create crafts, and get a photo with Santa. 
Event date: The pajama party is Friday, December 5, 2025, from 5pm-7pm, and Santa on the Farm is Saturday and Sunday, December 6-7, 2025, from 10am-3pm.
Insider tips: Buy tickets in advance to save money. Children under 2 are free.