Boston Winter Bucket List

Anyone else suffering from a small case of the post-holiday blues? I’m partially bummed and partially relieved myself. I have tons to look forward to (less than 100 days until the marathon!!) but I realized the other day while on a run that I want to bring more intention to my short winter days. These aren’t big lofty bucket list items, since a lot of my time this winter will be going to training for the marathon.. but hopefully just little things to push me to get out of the apartment and spend quality time with friends 🙂

Go snowshoeing/cross country skiing in Weston. Check!

Spend a Sunday at the Harpoon Brewery with friends.

Grab a drink at the Top of the Hub. Snag a view of Boston at the Skywalk Observatory during the day.

Get cozy at Thinking Cup, Trident Cafe and Tatte Fine Cookies & Cakes.

Make a date at Lucca Back Bay, Toro, The Hungry i, and The Salty Pig.

Go skating on Frog Pond.

Check out the Institute of Contemporary Art.

Wander the North End, making stops at Neptune Oyster and Modern Pastry.

Take photos along the streets of Beacon Hill during a snow storm.

Attend an event at the Society of Grownups in Brookline.

Go to the Brattle Book Shop.

Attend a pottery throwing class or wine & cheese night at the ClayroomCheck!

Go to the Museum of Science Planetarium.

People watch at the Precinct Kitchen + Bar, Back Bay Social Club, Revere Hotel.

Get my brunch on at Cafeteria, Estelle’s, and the Beehive.

See stand up comedy at Laugh Boston.


Boston locals: anything to add to my bucket list? Everyone else: what are you looking forward to this winter?

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  • Wow, that is a long list full of fun things! I did a summer bucket list but I think I maybe only did half the things on my list? But it’s a fun exercise to come up with some ideas.

    Winter is a tough time of year in Minnesota as it’s so dreary and so so so so brutally cold. So I am feeling pretty ‘blah’ lately. I don’t have a list of things I want to do, but I do want to go XC skiing every weekend that I am here between now and March hopefully. Besides that there is a museum close to my house that I want to check out one night with Phil for a date night.ReplyCancel

    • Caroline

      Yeah, if I do only half the things on this list I will chalk it up to a successful Boston winter! XC skiing sounds so fun, I’ve never been!ReplyCancel

  • Fantastic list! Salty Pig <3ReplyCancel

    • Caroline

      I know I love Salty Pig! I’ve only been there for a drink though, definitely want to go back.ReplyCancel

  • I wish I had seen this list more than a few weeks before I left – I haven’t done so much of this either! My 3 weeks & counting bucket list is hitting all my favorite runs, Life Alive, Oleana, Veggie Galaxy, lingering at the BPL, Sweat & Soul Yoga, and of course November Project.ReplyCancel

  • Snowshoeing! That would be SO much fun! Haha!ReplyCancel

  • That’s an awesome list of fun things to do!

    I keep thinking I need to get out and enjoy some winter activities, like we’ve been talking about going snow shoeing for weeks, but then I remember how BUSY my spring, summer and fall were last year so I’m just going with the urge to spend my free time reading and watching Netflix these days 🙂ReplyCancel

  • […] Local friends, this is a nice list of fun activities: Boston winter bucket list […]ReplyCancel

  • Ashley

    The Improv Asylum in the North End! We have been there multiple times and it never fails.ReplyCancel

  • […] friend and then went to the Clayroom to paint pottery and drink wine with another friend. (Another Boston winter bucket list item crossed off!) Sunday I mostly just relaxed and caught up on some work. I’m feeling […]ReplyCancel

  • […] Saturday — XC skiing. This is basically a workout.. right? It was super fun! And got to cross something off my Boston Winter bucket list […]ReplyCancel