This Season, Plan the Perfect Weekend with Cambridge’s Winter Festivities

Photo Credit: BioMed Realty and Kyle Klein Photography

Stepping out into the winter weather for a fun, festive day can seem exciting—but if you don’t have a plan, you might feel like heading back inside after just a few aimless minutes in the cold. Knowing where to find all the best winter and holiday-themed activities (and treats!) ahead of time can help you avoid that stressful, last-minute strategizing while you’re all layered up in coats and scarves, especially if you’re taking the kids—prone to complaining about the weather—with you. Luckily, in Boston, filling your winter weekends with energetic and lively experiences that’ll keep the whole family happy is easy. All it takes is a quick trip across the river (and enough hot chocolate to keep any complaints at bay). 

That trip across the river will lead you to Cambridge: a hotspot for joy and fun this winter, with an extensive and widespread calendar of activities that spans the whole season. For locals and visitors alike, Cambridge is the place to embrace all the seasonal traditions, shop local artisans, taste delicacies, enjoy entertainment and more—and with so much to do, it’s worth more than a day trip. When you’re looking to schedule a weekend that’s fun for kids and adults alike and makes the wintry outdoors not only bearable, but even enjoyable, here’s our itinerary for a quintessential Cambridge winter getaway. 

Day 1 

Before your weekend starts, you’ll want to drop off your luggage—and to get all the rest, relaxation and warmth you’ll need once the weekend kicks off, finding the perfect accommodations for your trip is key. At Porter Square Hotel, you’ll be located right in the heart of Cambridge, and start your day off in the center of the action. With coffee and breakfast options all around the area, like Flour Bakery for breakfast pastries and hot cocoa, you’ll be in the perfect spot to get fueled up for your day. Another option is to stay at Sonder 907 Main, a classic experience where you’ll enjoy exposed brick in a gorgeous brownstone with airy, light warmth. You’ll also be in the prime location for getting your day started with local boutiques, restaurants and taverns—and plus, if you arrive early, you’ll have easy luggage storage in the lobby.  

After you’re all checked in—or while you’re killing time before—activities await. To get right into the winter spirit and spend some time outdoors, you’ll find community ice skating in Kendall Square—and to keep exploring, visit Mount Auburn Cemetery, the setting for beautiful views and, beginning in December, an annual event called SOLSTICE: Reflections on Winter Light. SOLSTICE is an outdoor journey through the cemetery’s landscape that features large-scale light and sound artworks and features an indoor experience with live music and candle-lighting, and tickets are available online now. For an indoor excursion, take a trip to Craft Loft at CambridgeSide where you can get some crafting in, whether that’s to make some last-minute homemade gifts for loved ones or to make your own scarves to keep warm. 

Plus, don’t forget to grab some snacks, meals and drinks as you make your way through Cambridge (being sure to stop for some of the area’s classic attractions like Harvard Book Store). During these cold days, there’s no more appealing meal than soup, and to warm up with delicious broths, check out What a Soup for authentic Thai noodle soups and Yume Wo Katare for ramen. And to treat yourself during this mid-day pick me up, head inside the Royal Sonesta Hotel for a warm, intimate retreat with food, wine and art at ArtBar—where local ingredients make creative cuisines and a beautiful ambiance looks out over the Boston skyline. Plus, ArtBar offers the unique opportunity to enjoy the riverside views without bearing the cold: Their heated igloos are open throughout the winter, so you can create special memories while dining riverside and staying warm. 

Then, when evening rolls around, spend sunset on the water (in an enclosed boat, don’t worry) with the Charles River Boat Holiday Cruise. This one-hour event boasts stunning views while keeping you warm enough to enjoy them and serves delicious holiday cocktails for those inclined.  

And to cap off the night, Cambridge is known for its wide array of creative and unique bars and restaurants—and they’re also opportunities to stay in the holiday spirit. Macabee Bar, the only Hannukah themed bar in Boston, serves Hannukah-inspired cocktails and bites. Plus, opening in late November and running through Christmas Eve, the Kimpton Marlowe, a boutique Cambridge hotel, hosts Miracle, a winter bar that’s an annual pop-up at the hotel. Miracle features crafted seasonal cocktails, a fireplace ambience, bright décor and a holiday soundtrack. That means you won’t have to put your festive attitude to bed when you head back to the hotel—you’ll even be able to kick it up a notch.  

Day 2 

When you wake up for your second day in Cambridge, the first thing you’ll want is coffee—and the second one is to hit some classic, iconic winter events. With many happenings and pop-ups in Cambridge throughout the winter months, you can plan your visit around the events most exciting to you, and here are some of the season’s standouts for daytime excursions. 

For some local, eclectic, artistic shopping—while strolling through the heart of Kendall Square’s beautiful canal district—head to Cambridge December 6th and 7th for The Cambridge Arts’ Holiday Arts Market. From noon to 6 pm both days, check out a diverse catalog of media and art that can make for the perfect holiday gifts. And for some additional local shopping against stunning views, don’t miss Canal District Kendall’s Winter Market on December 15th, open from 11 am to 4 pm, and the Inman Holiday Market, with over fifty local vendors representing small businesses and handmade gifts, which takes place in Inman Square on December 22nd.  

Inevitably, all your exploring will make you hungry: And on December 21st in Brattle Plaza, visitors can enjoy the 15th annual Everyone Loves Latkes festival, a Hannukah celebration that serves complimentary latkes, jelly donuts and chocolate coins from 2 to 3 pm, with live music as entertainment. Or, stop for some hearty bites and sips at one of Cambridge’s many restaurants, like Lavash Grille for authentic Turkish and Mediterranean food, drinks and coffee, and Little Donkey for globally influenced fare. For a sports-bar atmosphere when you’re looking to dodge the cold, head to 730 Tavern for classic American eats.  

Once you fuel up, there’s no shortage of evening activities and events to round out your weekend in Cambridge. On November 30th, The Charles Hotel celebrates its annual Tree Lighting Celebration to kick off the holiday season, and the classic, bright event features a visit from Santa Claus, as well as sights, sounds and tastes of the season. For some entertainment throughout December, The Midwinter Revels is a production, featuring songs, dances and stories that represent traditions of Celtic mythology and fantasy, and themes of hope and optimism for a new year. Then, if you visit after the new year, you’ll find Boston Celtic Musical Festival happening with dates from January 16th to 19th. This festival spotlights Greater Boston’s traditions of music with professional touring acts and local talent, representing song and dance from Irish, Scottish, Cape Breton, Quebecois and other Celtic communities. 

No matter what time this season you make your Cambridge visit, there are opportunities to get into the spirit and enjoy all the things that make winter such a special time of year. Though New England weather will inevitably make us all freezing these next few months, that doesn’t mean we can’t find warmth in community and joy—and Cambridge is the perfect place to do that. 

To get started planning your trip to Cambridge this winter, click here.