Now that the Choose a Challenge staff is back from holiday break, we're already discussing where we want to go this winter season around the northeast. That inspired us to share with you guys some of the places--far and wide-- we either went over the break, have been before, or are looking forward to visiting before winter comes to a close. Looking for a weekend getaway? Avid skier? Fan of fun winter-related activities? Enjoy our staff picks below!


Mike's Pick: 
Killington, Vermont

"For the avid skier and/or the group of friends who just want a cozy winter weekend."
Killington's peak is 4,241 feet above sea level [Vermont]

Killington's peak is 4,241 feet above sea level [Vermont]

"I've been going to the  Killington ski resort since I was a kid. It's where I learned to ski and where college friends and I recently went for a reunion trip just last year. With 73 miles of skiable trails and a cozy surrounding town, you can't go wrong. I recommend starting the day off on the "easy rider" green trail and after a few runs if you're feeling confident there are a few more advanced trails you can merge on to. The best advice I can give you is to try to book somewhere with AirBnB for your accommodations in order to try and save some money."

Ash's Pick:
Montreal, Canada

"For adventurers who love to try new things and new foods wanting to experience all of the classic winter activities with a bit of Canadian flair." 
Inside the Montreal Holiday Markets [Canada]

Inside the Montreal Holiday Markets [Canada]

"Ever since I was a little girl, I've always wanted to go experience Montreal and see the sights and sounds of one of the most magnificent cities in the world. I've always wanted to go to a sugar shack, cabins filled with amazing food, or go ice skating in the center of town. My ideal evening in Montreal would include poutine, a holiday market adventure, and of course, snuggling up in a tea house and spending hours watching the snow fall outside the window." 


  1. Sugar Shacks - They are located on or near farms where fresh maple syrup is tapped. 
  2. Poutine - A 24-hour poutine restaurant. Poutine is best in Canada and that can't be argued 😁 
  3. Montreal Tea Houses - A wonderful place to relax and enjoy the blustery winter day.
  4. Holiday Markets - Always great during the holiday and winter season

Simon's Pick:
New York City

"Enjoying winter right in your own backyard."
Ice Skating in Central Park [New York]

Ice Skating in Central Park [New York]


"I'd probably have to go with Central Park or Rockaway beach. Both are a subway ride away for me and a reminder that you don't have to escape the city to get away. Rockaway is beautifully wild before/after the holiday season and pretty desolate, whereas Central Park is full of winter-time activities (especially for someone like myself not originally from NYC, who grew up watching Home Alone 2). Both spots are great but overly back home in London always wins during the winter and holiday season!" 🇬🇧

For More: Central Park Upcoming Events


Nick's Pick:

"Taking a weekend away for some much needed rest and sun."
Fort Lauderdale Beach [Florida]

Fort Lauderdale Beach [Florida]


"If you're anything like me, by the end January you've had enough of the winter and would rather be anywhere but in another snowstorm. Luckily, with the rise of budget airlines in the U.S. like Spirit, Frontier, and (my personal favorite) JetBlue, you can plan a winter getaway to somewhere warm for about as much as it would cost in gas for two, 6-hour drives. At the end of January and into February (barring travel holidays like President's day) you can find AMAZINGLY cheap flights to some nice places where you can soak in some sun. For example, as of writing this, I found round trip tickets to and from Orlando, Miami and Ft. Lauderdale airports for $90-$120 and that is super cheap. Moreover, January-March is typically considered "slow season" more often than not for summer destinations like these, so once you're there you can expect low prices as well. Time to call up some of your friends in Florida and ask them if they have an air mattress!

I personally search all my flights on which not only finds you the cheapest flight, but looks for hidden/unlisted seats on major hauls that are often 50-90% cheaper than listed seats for the same flight! If you get the "seasonal sad-times" like me, or just want to go outside and not feel like your toes are about to get frostbite and fall off I HIGHLY recommend taking a weekend away for some much needed rest and sun."