Here are the top must-do activities in Boston during Winter including events in Boston Winter Wonderland:
1
Stone ZooLights
A short drive north of Boston is home to a manageable and fun Stone Zoo in Stoneham, MA. Each winter, they offer their famous zoo lights called ZooLights. We often go beforehand to their “Hot Chocolate With the Reindeer” event which is a fun up-close look at the Sven-like creatures. You can grab your family, put on reindeer ears they hand out, and munch some yummy treats before the zoo lights begin. The stroll around the zoo is quite fun, and you’ll get to see the beautiful pink flamingos amid a background of colorful lights. Franklin Park Zoo also has a magnificent lights experience as well if that’s more convenient.
2
Outdoor Boston Food and Chocolate Tours
One of the BEST things about being a local in Boston is we aren’t afraid of no snow! When I lived in Chicago, the folks in the windy city definitely hibernated. But we are tough New Englanders, and we don’t mind bundling up. In fact, some Decembers are practically a balmy 45 degrees — do you even need a coat!? So sign up for one of our weekly tours (yes, we’ll even serve ya ice cream in the winter!), grab your hat and warm coat, and let’s explore the neighborhood!
Check our Tour Calendar For Booking Availability This Week!
3
Solstice at Mt. Auburn Cemetery
Our family really enjoys the SOLSTICE light show at Mt. Auburn Cemetery which happens every December and sells out quickly! This year, we decided to buy Enhanced Tickets to the show, which included free food and drinks as well as a warm place to start the event and private bathrooms as well as free parking. In fact, it was worth it for the experience as the food was delicious – from chicken skewers to delicious butternut squash soup to macaroni and cheese with mushrooms to yummy brownie bites and hot apple cider or hot chocolate. The event itself is a longer walk, so definitely plan in advance for a 60-90 minute walk. Our favorite included the lantern walk, reflections of light on the gothic chapel, and lighting a candle inside with a violin playing. An immersive, impressive experience!
4
Winterlights at Canton’s Bradley Estate
The Trustees currently offer two sparkling gardens of their famous Winterlights. Our favorite of the two is the Eleanor Cabot Bradley Estate in Canton, Massachusetts which even has a row of lights set to music. We did also enjoy the Stevens-Coolidge house but as of 2025, they’ve stopped offering that winter walk in order to preserve the gardens. You’ll also be able to enjoy some hot chocolate and a scavenger hunt on the Canton walk as well as candy cane lights and immersive light tunnels along the way.
5
Festival of Trees @ Elm Bank (Wellesley, MA)
The Massachusetts Horticultural Society also offers a yearly Festival of the Trees at Elm Bank which is where we got married and absolutely love! The walk is definitely the shortest of the ones we listed, and they also offer hot chocolate for the family. Inside there’s an elaborate train display which is a lot of fun to explore. Our favorite is the whimsical Weezie’s children’s garden — you’ll have fun on this manageable stroll and fun winter outing with your loved ones.
Conclusion: Go Outside and Explore Boston This Winter!
Don’t let winter slow you down! It’s still a great time of year to explore the outdoors. Join us on a winter walk on one of our neighborhood food tours or try one of these fun experiences as well. We can’t wait to explore with you!
Warmly,
Lizzie and Sam
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