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’Tis the Season: How to Celebrate the Holidays in Boston

The weather outside may be frightful at times, but Boston during the holiday season is always delightful. According to Greg Lazzaro, Life Enrichment Director of Waterstone at the Circle, there’s no better time to visit this historic city and experience the joys it has to offer. 

“Don’t let the cold fool you – Boston is hot, hot, hot during the months of November and December,” he says. “There are so many wonderful events, celebrations, festivals and more going on in our historic city throughout the holiday season. Every year, we host hundreds of thousands of visitors to our fair city and put on a spectacular display of holiday happiness and hospitality. It’s truly a magical time.”

Whether you’re simply visiting Boston during the holiday season, are a new resident or are a lifelong Bostonian, we’ve put together some of the holiday highlights for 2019. 

Thanksgiving Events

What better way to celebrate Thanksgiving than in the state where it all began? As you may imagine, Thanksgiving in Boston and the surrounding area is an entertaining blend of history, fun and (of course) delicious food. Here are some of the top events and can’t-miss opportunities for celebrating and giving thanks. (For more events and activities, visit the Boston Discovery Guide’s Thanksgiving Events page.) 

Step Foot on Plymouth Rock

Yes, this isn’t in Boston proper, but there’s no better way to celebrate Thanksgiving Day than in the historic town of Plymouth. Head south on MA-3 for a jam-packed day of parades, festivities and celebrations. Learn all about the history of Thanksgiving and America’s earliest settlement at the annual Thanksgiving Day in America’s Hometown. Enjoy a Thanksgiving Day Buffet at Plimoth Plantation, take in America’s Hometown Thanksgiving Celebration & Parade and enjoy a Patriotic Concert in Plymouth Memorial Hall. 

Set Sail for Food & Fun

Start a new Thanksgiving tradition on a Thanksgiving Day Cruise along historic Boston Harbor. Enjoy a buffet feast, DJ entertainment, interactive games and a dance floor. All you need to do is relax and enjoy quality time with your loved ones … and, of course, bring your appetite. Cruises run November 28 through the 30th.

Get Stuffed 

Of course, no Thanksgiving is complete without a meal with family and friends. Many fine Boston restaurants offer a spread of epic proportions on Thanksgiving, so feel free to turn the oven off this year and let someone else serve you instead. Standout spots include Boston Harbor Hotel, L'Espalier, Parker’s Restaurant, and others. Check out a full list of restaurants here – and be sure to make reservations ASAP. 

Christmastime Holiday Celebrations

The fun doesn’t end on Thanksgiving – in fact, it’s only just begun. The holiday season in Boston is, in a word, magical. The city and surrounding areas transform into a festive wonderland of lights, special holiday music and shows, spectacular decorations and lots of good cheer. We’ve listed some of our favorite events, but you can check out a more comprehensive list on Boston Guide’s Christmas in Boston events page.

Be Dazzled by ZooLights

The annual ZooLights celebration at Stone Zoo is a much-loved tradition by Bostonian families. The zoo’s paths become a wonderland of twinkling lights that enchant adults and kids alike. Enjoy hot chocolate, marshmallows roasting over the fire pits and, of course, a visit from Santa. Grown-ups can relax in the Lord Hobo Holiday Beer Garden and enjoy exclusive beers from Woburn's Lord Hobo Brewing Company. 

Be Wowed By Macy’s Windows 

On Black Friday (November 29), the historic Macy’s in Boston's Downtown Crossing lights up the night with the unveiling of their famous holiday window displays. The evergreen trees become a magical forest of Christmas lights, the window displays enchant and visitors are wowed by special performances from Santa (and this year, singer-songwriter Natasha Bedingfield, Urban Nutcracker and the Tufts Beelzebubs as well).

Enjoy Tree Lightings
Nothing says “kick off to the holidays” more than one of Boston’s beloved tree lightings. Many of these take place on Thanksgiving evening, meaning that by December, the city is all decked out in its holiday finest. Tree lighting ceremonies are chock full of free live entertainment, delicious food, joyful crowds and appearances by Santa and his reindeer. 

  • Boston Common: The much-loved Boston Common Holiday Tree Lighting ceremony will be held on December 5 from 6:00 p.m. – 8:00 p.m. The Mayor’s Tree is lit, followed by illumination of the dozens of other trees lining the Common. Don’t miss the free ice skating show and fireworks. 
  • Faneuil Hall Marketplace: See the largest Christmas tree in Boston as well as a spectacular “Blink!” light show (performances every half hour 4:30 – 10 p.m.). Kick off the celebration with the 33rd Annual Boston Tuba Christmas on November 30. Then, return on December 3 for the official tree-lighting ceremony.
  • Seaport Common: Gather on Seaport Common Friday, December 6 for live holiday tunes, an interactive art installation, a tree lighting and fun for the whole family.
  • Copely Square: This historic center lights up on Monday, December 2 along with appearances by holiday favorites Rudolph, Frosty and Santa and live performances from local groups. Prior to the event, the Boston Public Library holds their annual Candy Cane Tea featuring the hanging of the wreaths, a menorah lighting and fresh-baked cookies. 

Go Ice Skating

Strap on your skates and hit the ice at some of the nation’s best and most historic ice skating rinks. Outdoor fun can be had at Boston Common Frog Pond and Kendall Square, or Patriot Place if you prefer an indoor ice experience.

Enjoy a Holiday Concert

The performing arts scene in Boston is one of the best in the world, and it’s never more apparent than at the holiday season.

  • The Nutcracker: This much-beloved classic takes the stage in several different ways. Enjoy a traditional favorite performed by the Boston Ballet throughout the month of December, or take in a one-night-only performance by the Moscow Ballet. Don’t miss a unique performance of Urban Nutcracker, an inventive inner-city reimagining of the classic, now in its 19th year.
  • Holiday Pops: Led by director Keith Lockhart, the world-famous Boston Pops returns with their spirited Holiday Pops. Enjoy classics and new arrangements of holiday favorites along with sing-alongs and photos with Santa.

If you’d like to learn more about holiday events in Boston, or if you’re wondering how a luxury senior living community like Waterstone at the Circle can help you live an active and fulfilled life, contact us today at 617.431.1880.

Luxury Senior Living in Boston

Waterstone at the Circle, located in Boston’s historic Cleveland Circle neighborhood, is more than just independent living in Boston … it’s a sophisticated urban setting for today’s active seniors. Enjoy best-in-class service and an urban lifestyle with arts and cultural, and historical attractions right outside your front door. From high-end amenities to gourmet dining and more, experience the best of city and suburban life at our upscale senior living community located on the crossroads of Brookline and Chestnut Hill. 

Elegant Independent Living Apartments

Each of our 92 independent living apartments is the height of luxury and modernity, with sophisticated design, upscale features and stunning views of the city. Create the urban senior living experience you want with one- or two-bedroom apartments, a variety of floor plans and monthly rentals.  

Senior Living Supportive Services

As an over-62 community, residents may require support from time to time. That’s why we’ve developed an on-site coordinated care program, in cooperation with our premier community partners, that allows our independent living residents to receive the assistance they need.

The best part? Residents don’t have to leave our senior living community – or even their apartment – to receive high-quality support. They can receive the services they need, when they need it, in the comfort of their own homes or in our on-site therapy gym.

Waterstone at the Circle is the opposite of retiring… it’s a place to enhance your active, on-the-go lifestyle. Call617.431.1880for more information or to schedule a visit to our premier Boston Independent Living community and discover The Circle lifestyle today!