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.

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.

Saturday:

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.

Sunday:

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 taking 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.