City Guide: 48 Hours in New Canaan, Connecticut

I’m a big believer in using up one’s vacation days. Planning a trip, taking time off, and having something to look forward to on your calendar does wonders for self-motivation at the office. I am always surprised by how rejuvenated I feel after escaping the city, even it’s just for a weekend away. One of the many incredible things about our dear city is that there are so many options for weekend getaways with no car necessary. I am entirely biased, as I grew up there, but I put together a weekend agenda for a casual retreat to New Canaan, CT that feels light years away from the hustle and bustle of Manhattan. Simply hop on the Metro North train at Grand Central, and you’re on your way to an R&R weekend in the country. I recommend the Roger Sherman Inn as your home base for the weekend. It epitomizes the quaint, colonial feel of the town and is a cozy spot for drinks after dinner as well. Here’s how I recommend you spend 48 hours in New Canaan, Connecticut.

City Guide: 48 Hours in New Canaan, Connecticut

Friday Night:

Hop off the train in downtown New Canaan and walk over to Sole for dinner. Post up at the bar with a glass (and by glass, I mean bottle) of vino, and order the flash fried calamari and the pizza with arugula and prosciutto. It’s already a good weekend.


Fuel up for a day of exploring at the cozy Connecticut Muffin on Main Street. I always order the exact same thing: a homemade blueberry muffin, toasted with butter. Grab a fresh-squeezed OJ and a coffee and you’re ready to roll.

If you can resist scarfing down that muffin on the spot, head over to Waveny Park and enjoy it there. This former summer estate is now a public park, and you can wander through miles of hiking trails, and also explore the main mansion, which is a stunning Tudor-style home.

Head back to town for lunch after a morning in the great outdoors. I’m giving you two options here, depending on if you’re feeling naughty or nice. If you ate that whole pizza at Sole last night (any pizza is a personal pizza if you try hard enough), head to Baldanza, a little farm to table cafe on Elm Street. My personal favorite is the mixed bag kale salad, and don’t forget a mason jar iced coffee. If you’re feeling naughty, don’t miss Station Eats for a Station Burger, fries, and a shake. It’s pretty much the New Canaan equivalent of Shake Shack.

Spend the afternoon taking a guided tour of Philip Johnson’s pièce de résistance, the Glass House. Book a tour online in advance, and go and soak up the incredible grounds and history of this landmark New England architectural gem.

Dinner will be a Chef Luis, where you can’t go wrong with a single thing on the menu. Namely tacos. Tacos are always a good idea.


No lazy Sunday morning is complete without brunch, and New Canaan happens to be home to my all-time favorite brunch spot, Rosie’s. Order the huevos rancheros (I dream about this, seriously) and a bloody mary and enjoy pure bliss. The baked goods are also amazing there, so save a little bit of room for a treat.

Spend the day shopping around downtown New Canaan, which boasts an impressive array of home and antique shops. Elm Street Books is the best place to start; it actually connects on the interior to Rosie’s. I’ve been coming here since I was a kid, and it has a classic, small-town feel, as well as a very well-edited selection of reads. Other shops not to miss are Design Solutions, The Wave, Karen Forbes, and The Whitney Shop.

If you need a bit more caffeination, swing by Zumbach’s, the local haunt for good coffee. All of the high schoolers work there, and they have an incredible selection of beans that they roast themselves. I highly recommend grabbing a few freshly-ground pounds to bring back with you to the big city.

After you’ve thoroughly considered staying forever, hop on the train and head back home (they run every hour, and the train station is right in town). Congratulate yourself on making the time to explore a new place and get out of your usual weekend routine. Hopefully you feel re-energized for the week ahead (not to mention full, and hopefully slightly more cultured). No Sunday scaries here.

By Carolyn Stine: Carolyn is the Commerce Experience Manager at Club Monaco, but her heart (and stomach) lies firmly in the food and travel universe. Despite working on the digital side of the fashion industry by day, you can most frequently find her in search of the best new restaurant, knee-deep in planning a trip to a far-reaching locale, or at her local branch of the New York Public Library. Follow Carolyn’s adventures on Instagram at @carobaker1.

Image via Classy Girls Wear Pearls.

20 Responses to City Guide: 48 Hours in New Canaan, Connecticut

  1. Rosie says:

    Thanks for coming in and for featuring us on your blog! We’re glad you’re a fan!!! ❤️ xoxo Rosie

    • Carolyn says:

      Hi Rosie,

      Thank you so much! I grew up in New Canaan and still come back every time I go home 🙂


  2. Caroline says:

    I’d like a personal tour this summer please 😉

    Sounds like the perfect weekend!!


    • Carolyn says:

      Hi Caroline,

      It really is such a great weekend away, glad you enjoyed the article!


  3. This sounds like a great place for a weekend getaway! I hoped on the ferry from Long Island and went to New London and Providence for a few days. It felt great to get away and not be too far from home!

    • Carolyn says:

      Hi Vanessa,

      Glad you enjoyed the article! I’ll be in New London next weekend – great minds think alike 🙂


  4. Great picks for a NC get away. Lots more to add. The River is a must see and can take a whole afternoon or simply and hour. Also don’t forget the delicious gelato at Gelatissimo. So much more to do one will just have to come back!!
    If one wants a rejuvinating health oriented weekend. Let me know. I will plan it for them.

    • Elana Lyn Gross says:

      Thank you for your recommendations, Elizabeth! I just emailed you about writing a guide for a rejuvenating health oriented weekend. What a fun idea!

  5. Anna says:

    This sounds like an awesome city to go to for a weekend!
    -Anna |

  6. Laura says:

    Sounds like a great time!

    Laura |

  7. Jenny says:

    Sounds like a very relaxing weekend 🙂

    xoxo, Jenny

  8. Mindy says:

    What a wonderful area! I’d love to visit. Xoxo Mindy

  9. Alix Maza says:

    Love it! Definitely on my travel bucket list now.

    Alix |

  10. Savannah says:

    I’ve only been up north to visit New York City, but I really hope I can go back soon! CT and Vermont are my two dream places to visit.

  11. Cristina says:

    I’d love to visit here! Short trips are always fun because they’re jam packed with lots of things to do and see 🙂


  12. I would love to visit Connecticut one day. I was thinking the fall would be nice since we don’t get a lot of fall tree colour here.

  13. Stephanie says:

    This sounds like such a fun weekend getaway! I’ve never been to Connecticut, but it sounds lovely. I’ll definitely have to put it on my list!

    Stephanie |

  14. Ashley says:

    What a fun post! I would love to visit!

    xo Ashley

  15. I definitely take advantage of my vacation days too. There’s too much fun to be had and too many places to explore to just sit at home and sleep! I’ve never been to Connecticut, but it sounds like you had a fun time! I’m glad you enjoyed your mini vaca!

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