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1. Victorian Christmas – Irvington

Head to Washington Irving's Sunnyside for a one-night-only, Christmas-themed tour of the house, complete with crafts and donuts. The event is on Saturday, December 20, 2025, and reservations are required.

Why it’s unusual or underrated: It's always worth taking advantage of the charming historical sites in our area, whose charm increases even more when dressed up for the holidays.
What visitors can expect: A cozy tour of a beautiful home and a paper craft to take home with you.
Insider tips: Tours run an hour and a half, so be sure everyone is in the mood for a walk.

2. Ride on the Polar Express – Kingston

The Catskill Mountain Railroad offers a vintage train ride experience all December, complete with cookies, hot chocolate, elves, and storytime. While it might not make it all the way to the North Pole, it's close enough.

Why it’s unusual or underrated: These 1950s coaches are the real deal, and the ride promises to be especially magical for young kids.
What visitors can expect: A train ride with plenty of entertainment that lasts over an hour. Plus a souvenir sleigh bell!
Insider tips: Make sure to arrive at least half an hour early for boarding.

Celebrate the winter solstice at Olana with a variety of fun activities. Photo courtesy of Olana

3. Olana Winter Solstice Celebration – Hudson

Head to Olana State Historical Site on Saturday, December 20, 2025, for a festive wintery day complete with a bonfire, storytelling, choir performance, and more.

Why it’s unusual or underrated: Olana's Solstice Celebration is a great non-denominational destination for all winter lovers.
What visitors can expect: Along with all the other attractions, Olana's miniature donkey, Hank, is taking visitors.

4. Clay Art Center Handmade for the Holidays – Port Chester

For one-of-a-kind handmade gifts and ornaments, head to Port Chester's Clay Art Center on Tuesday, December 23, 2025, and take home something as special and unique as you are.

Why it’s unusual or underrated: Not just any holiday market, shopping at the Clay Art Center supports local and nationally recognized artists.
What visitors can expect: Pottery, ornaments, tableware, sculptures, and more.

5. Charles Dickens’ Christmas Carol – Sleepy Hollow

Running from Saturday, December 13-Sunday, December 21, 2025, master storyteller Jim Keyes spins the tale of Ebenezer Scrooge for kids and grown-ups alike.

Why it’s unusual or underrated: This one-of-a-kind performance takes place in the historic Old Dutch Church and includes musical accompaniment.
What visitors can expect: A 60-minute classic tale for ages 10+.
Insider tips: The church is not heated, so bundle up!

6. Nutcracker, Short and Sweet – Peekskill

Peekskill's Paramount Theater offers a performance of The Nutcracker for a younger set on Sunday, December 21, 2025, complete with Tchaikovsky's classic themes, dancing, and narration.

Why it’s unusual or underrated: A great option for kids who might not have the stamina (or volume control) for a full-length version of the ballet.
What visitors can expect: Another 60-minute performance, but for kids as young as 3.
Insider tips: Check out some of Paramount's other seasonal events, like Jessica Lynn's Very Merry Christmas.

Tarrytown is home of a stunning and unique Festival of Lights celebration. Photo courtesy of Shames JCC

7. Hanukkah: A Festival of Laser Lights – Tarrytown

What better way to celebrate the festival of lights than a laser show? The Tarrytown JCC is hosting its unique Hanukkah celebration on Saturday, December 20, 2025, at 4:30pm.

Why it’s unusual or underrated: It's a Hanukkah laser show!
What visitors can expect: Hannukkah+Lasers and fog machines. 'Nuff said.

8. Holidelic – Tivoli

For a funky holiday experience that's equal parts Santa and George Clinton, head up to Tivoli's Kaatsbaan Cultural Park and see Grammy-nominated Everett Bradley and his ensemble on Friday, December 12, 2025.

Why it’s unusual or underrated: Christmas+Funk is right up there with Hannukkah+Lasers. That's not an opinion, that's math.
What visitors can expect: This is an 8pm show that's 90 minutes long, so definitely for teens and not kids...or maybe just for a date night.