Boston’s Winter Wonderland

From the season changes to the beauty of the city, Boston is always a wonderful place to walk around. Despite the cold weather, hundreds of Bostonians (and travellers) make their way into town for winter festivities. There are tree lightings, Christmas celebrations, ice-skating on Frog Pond, ballets & theatre shows, and now Boston Winter – my new favorite. 2016 saw Boston Winter open later than planned due to unexpected warm weather. Located at Boston City Hall, the festivities are endless. You can meet Santa, drink wine (and cocoa), shop, skate, eat (way too much sugar), and more. I was extended an invite to visit thanks to my friends at The Grommet who have a Pop Up Shop at this year’s event.

Isn’t their shop the cutest? All of the shops at Boston Winter were tiny little cottages with select products. Many of them small, local businesses where products are hand-crafted. The Grommet is one of those shops where you can find unique trinkets to give to friends and family as tokens of appreciation (or gifts). They had some wonderful options and you can check them out online if you don’t get the chance to visit in store.

So… what is The Grommet?

“We launch undiscovered products and help them succeed; we call them Grommets. Grommets aren’t just things. Grommets are products with a purpose invented by people with stories. Buy differently.

How do we decide which products and companies are “best?”  First, they must be true innovators. Second, they must have rich stories to share (often full of blood, sweat and tears). Third, they must be built on strong values.  Those values can include preserving a handcraft, solving a problem in a fresh way, creating jobs in a struggling or developing region, building a social or green enterprise, manufacturing in the USA, or inventing new technologies. “

A few of the successful companies The Grommet has helped launch are Yoga By Numbers, Cord Buddy, Sleep Sheperd, Easy Arranger, PlayTape, Flip Belt, Maria Shireen, and Guardian Bells.

Another one of my favorite Boston-based businesses, Lovepop, had a shop location. Known for their pop-up shops all over the city, Lovepop has the perfect laser-cut, 3D greeting cards to give to everyone you love!

{Check out my post about Lovepop back when I first worked for them here –> Leap Into Spring With Lovepop}

Out of the 40 boutique, European-style “chalets” featured at the event, most were local vendors! FA few others included Etsy Artists of Boston, The Black Dog, LuLaRoe, Boston pro Shop, Boston Public Market, NuraBella Jewelry, Christmas and City, and Boston Olive Oil Co. (yum).  With a wide variety of options in categories of accessories, specialty gifts, ceramics & glassware, clothing, cosmetics, home & garden, jewelry, ornaments & decoration, and food & beverage you are likely to head home with a jolly bag full of gifts!

Boston Winter had a 20-foot Christmas tree powered by stationary bikes (so crazy!) and a gorgeous ice-skating path which you can see somewhat in my photo of the BOSTON sign above. This is right in the center of the ice rink which looks around the event space. There had to be at least 100 attendees gathered waiting for the Zamboni to finish up so they could skate. The ice looked about perfect and I wish I had brought my skates!

Finish up skating and enjoying a piping hot mug of cocoa, beer & wine inside of the Urban Lodge which was designed to resemble a classic ski lodge. In addition to the lodge there are specialty wine and chocolate tastings for all the merriest attendees to enjoy. Watch live entertainment at the center of the event! It’s hard to miss the talents who are playing out in the cold.

TIP: This is a great place to go during the week when there are less crowds and it is the perfect spot for a festive holiday date.

Find tickets for special attractions and event hours here –> Boston Winter Attractions

Of course no visit into town is complete without an evening stroll and a bite to eat. First we stopped at Union Oyster House where we ordered fresh oysters! They are famous for their clam chowder and for being one of the oldest restaurants in MA. The service was great and we even got to see good ol’ Benjamin Franklin hobbling around. The Union Oyster House is located just a few steps from Faneuil Hall and Quincy Market. It is a short walk from Boston’s City Hall Plaza.

We parked nearby the Boston Common and walked to City Hall Plaza. The trees were lit up and we saw Christmas carolers which I found to be very exciting. I have never actually seen carolers walking around the city before. They were dressed up in traditional holiday garb and looked adorable. Not too far from the carolers around Boston Common was a small group playing classic Christmas songs on instruments. Walking around town this Sunday night was a true holiday experience!


Here are a few other holiday attractions I suggest taking a trip for next time you plan a trip into the city:

  1. Frog Pond skating
  2. Boston Common tree lighting
  3. Liberty Hotel’s hanging trees
  4. Boston Ballet’s ‘The Nutcracker’
  5. Boston Pops holiday shows
  6. Faneuil Hall & Quincy Market tree
  7. Newbury Street holiday shopping
  8. First Night – Celebrate New Years!

Check out the Boston Discovery Guide for more here –> Discover Christmas in Boston


What are your favorite events, shopping spots, and restaurants to experience during the holidays?