My Winter Bucket List!

Bows & Sequins' Winter Bucket List: The Top Ten Things to Do & See

It’s the official first day of winter! Kind of depressing to realize the season hadn’t even started even though the temperatures have been in the negatives, huh? At the start of each new season, I always like to make a little checklist of things I want to do over the next few weeks and months. It always helps me stay on track! Whenever I forget to make or put off making my list, I feel like the season flies by and I’m left wishing I would have made time to plan those things I wanted to do. (Here are my lists from 2014/2015 and 2013/2014 in NYC!) Here’s what’s on the docket for me this winter in Chicago and beyond…

  1. Book a trip to Aspen! Ever since my trip last year, I’m dying to go again. (#goalz to have a place there one day!) I’d ‘settle’ for Deer Valley, Breckenridge, or Sun Valley, too. Who wants to plan a trip?!
  2. Go Ice Skating! It’s been years since I’ve gone skating. A little nervous that I may break a bone, but it could be fun! Crowds and touristy attractions are never my cup of tea, so Millennium Park by the Bean wouldn’t be my first choice. I’m thinking of the Sky Rink at the Peninsula instead… A little bit more off-the-beaten path!
  3. Find the most delicious hot chocolate in Chicago. Any recommendations?! City Bakery in New York was always my favorite! Dreaming of those giant marshmallows right about now…
  4. Bundle up and go for a walk along the lake. On an abnormally warm day last winter (I think it was 40 degrees ), I took a walk along the lake to clear my head and it was so peaceful and glorious. Whenever the temperature does creep up back up above freezing, I want to make it a point to get outside! (Read my thoughts on getting outside more here!)
  5. Have a baking day! I’m admittedly not the best cook (not the worst, either!), but I absolutely love baking. Problem is, I try to not let any of those delicious treats step foot in my apartment, so I rarely ever bake. It’s so therapeutic though! I need to set aside a day to spend in the kitchen with my mixer and plan on delivering those treats to everyone else. A little way to beat the winter blues! (PS: Did you know they now make a mini KitchenAid Artisan Mixer?! Such a better size for small city apartments! Coming from the girl that has the full size that takes up about half of my total cabinet space.. ha!)
  6. Go Sledding! Again, haven’t done this in YEARS. I don’t even remember the last time I went sledding, actually. When it started snowing a few weeks ago, I saw a bunch of kids ‘sledding’ in a park near my apartment (it’s completely flat) and it looked so fun! I’m headed to Lake Geneva with some friends for New Years weekend and would love to find some hills up there to have a little snow day. PS: Any recommendations for Lake Geneva in the winter?! Send them my way!!
  7. Try 10 new bars and restaurants in Chicago! It can be easy to fall into the trap of staying in more often than not in the winter… At least for me! Braving the cold is not my strong suit. But I want to get out and try at least ten new spots! I’ve got quite a few on my list to try so far… I’ll keep you posted and add them to the travel guide if they’re good!
  8. Go to a Bulls game. I’ve already been to a Blackhawks game this season, but would love to go to another few games at the United Center. Always a fun indoor activity! Until you can’t get an Uber afterwards… 😂
  9. Volunteer. I’m truly embarrassed by how long it’s been since I’ve done any sort of philanthropy work. (And to think I was the philanthropy chair for a year in college…) Sure, I’ve donated money recently, but I haven’t volunteered my time for a cause that I’m passionate about for quite some time.
  10. Visit Caneel Bay again! This is more of a wish list thing rather than a checklist item, but the three short days I spent there last December were such a tease. I’ve been itching to go back ever since! Very much in need of a no-work vacation off the grid with limited use of my phone and computer. Plus, I’m going to need to thaw out at some point from this frigid weather we’ve been having in Chicago. Accidentally realizing I never actually posted on the blog about this trip… But you can see a few more of the snaps from the trip here, here, here, here, here, here, & here! I’ll dig through my files and try to get a real recap post up soon…

What’s on your Winter Bucket List this year?! Would love to hear!

PS: If you haven’t seen these amazing snow tubes, you have to check them out in the scroll bar below!

Current Faves

Leave a Comment


  1. 12.21.16
    Rena said:

    On my winter bucket is that I will go to the sea as I live near the Alps 🙂
    xx from Bavaria/Germany, Rena

  2. 12.21.16
    S said:

    There’s a restaurant called Hot Chocolate in bucktown that’s pretty legit.

    • 12.21.16
      Jessica said:

      I’ve been there actually! It was years ago for dinner though, and I don’t think we tried the hot chocolate. I’ll have to stop by during the day and try it!

  3. 12.21.16
    Emily said:

    West loop bars like West End run free shuttles to and from the United Center. But it’s also under a mile to walk there after the game bc you might spend more time waiting for the shuttle than it would take to walk. Or The Ogden.

    • 12.21.16
      Jessica said:

      West End is so close that I would feel silly waiting for a shuttle!

  4. 12.21.16
    Bri said:

    I love Katherine Anne Confections for hot chocolate! My favorite is getting a sampling of three different kinds with a friend. ❤️

  5. 12.21.16
    Sarah Allen said:

    How did I not know about ice skating at The Peninsula! I just sent it to my mother in law. Might have to check it out while they are in town. Thank you!!

  6. 12.25.16
    Angela said:

    Lake Geneva is awesome! The Grand Geneva has sledding. And Egg Harbor and Simple Cafe in downtown are great for brunch!

  7. 12.25.16
    Alana said:

    Mindy’s Hot Chocolate in Wicker Park!! You can share it with someone- I found it to be too rich to finish. But amazing

    • 12.25.16
      Alana said:

      ahh i see someone already recommended whoops!

  8. 12.30.16

    such a great list!

  9. 1.8.17
    Laurie said:

    I love finding new things to do and places to explore in my town and nearby. Love your list, thanks for sharing!