Finish up that candy in your pumpkin (we’ll take it if you need help) because it’s November now, which means we’ll be inside of the holiday season snow globe and/or seasonal affective disorder light chamber for *checks notes* the next two months.  It’s always a magical time in New York City and the surrounding region — and to help you ease into it, we’ve put together a holiday agenda for you, just sprinkle in a little Great British Bake-Off (there’s a new season!) on the couch between adventures.

Whatever you do, consider taking mass transit when you do decide to head out — you do not want to deal with holiday season traffic.

Bonus: Find our winter guide here.


Armour-Stiner Octagon House
The Armour-Stiner Octagon House
  • Straight out of something you'd expect to see in the Gilmore Girls' Stars Hollow, it's the 25th Annual Charles Dickens Festival in the Village of Port Jefferson. The event will magically transform the area into the Dickensian era with streets filled with roaming characters such as Father Christmas, Dickens Mayor, Scrooge, the Town Crier and the beloved chimney sweeps.

  • There's a Dickens offering off Metro-North, too, inside the historic Old Dutch Church in Sleepy Hollow. Here, master storyteller Jonathan Kruk will regale you with his adaptation of A Christmas Carol.

  • For another period experience ('tis the season!), make your way to the unique Armour-Stiner Octagon House (yes, it is eight-sided) in Irvington to see how Christmas was celebrated in the Victorian era.

  • Because there’s nothing like surrounding yourself in twinkly lights around the holidays — check out our guide to more of the best spots where you can do this, all accessible by mass transit. 

  • Enjoy some outdoor ice skating all over NYC — glide on over to any of these rinks around the boroughs. 

  • Speaking of rinks, there’s a small one over at Industry City, which is a wonderful one-stop-shop holiday destination — there’s plenty of shopping to be done here, and once you’ve crossed some gifts off your list, you can sit back and relax by a fire pit and some warm food. 

  • Take a break from your holiday baking and feast your eyes on Gingerbread NYC: The Great Borough Bake-Off at the Museum of the City of New York, where bakers show off their skills to depict “Iconic New York City” in gingerbread. 

Zwilling Cooking Studio's chef demonstrating ravioli filling in front of two students
Photo by Zwilling Cooking Studio.
  • Want to step up your own baking game? Here’s a guide to holiday cooking classes, all accessible by mass transit. 

  • Need a break from all this holiday chaos? Enjoy a pint, or several, at one of Long Island’s fantastic breweries.  

  • Don't forget: Governors Island is now a year-round destination, and as the weather gets cool expect it to go through a winter transformation. You'll find plenty of public art, food, and seasonal activities.

  • Holiday markets are popping up all over and offer unique gifts in a delightful open-air experience. Check out our guide and start stuffing those stockings.

  • At some point, you’re likely to find yourself near Rockefeller Center this season (this year's tree arrives on November 11th and will be lit on the 29th), so bookmark our guide and you’ll know exactly what to check out and where to eat.  

NYBG Holiday Train Show (Courtesy of the NYBG)
  • Check out the whimsical holiday train show at the New York Botanical Garden this season (November 17th through January 15th), and make it a double feature by swinging by The New York Transit Museum's beloved Holiday Train Show (November 16th until February) at their Grand Central outpost.

  • Pizza slices, they look like Christmas trees, no? And you'll find the best ones off of Metro-North in New Haven — just check out our guide before you head there because planning is important when it comes to pizza.

  • Stroll through winter wonderland Central Park while learning which movies have featured the park during the holidays at their Winter Movie Tour. 

Our events calendar is regularly updated, so keep checking throughout the season for even more events around the region. And as always, check before you head out. 

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