Winter Fun in Boston: Holiday Activities and more!
Disclaimer: We are not paid to promote any restaurant, hotel, activity, product, or attraction. All opinions are subjective and based on our personal experience. Your experience may be different.
Update: I’ve done a lot of exploring during my years living here. I recommend checking out my massive New England travel guide for the best things to do across the region. One of the best things about living in Massachusetts is the easy access to so many other wonderful states.
Boston may not come to mind immediately as your top spot for spending your winter vacation, however, there is plenty of fun to be found in and around the city. Since moving to the metro, we have had no problem finding fun things to do no matter the season. I actually love the winter season. It’s quiet most of the time, I love ice skating, and there are usually tons of festivals and holiday light displays to look forward to. A cold winter is not as bad as everyone says.
Mike and I recently headed downtown for the Boston Common Tree Lighting. Neither of us had been to a bit city Christmas lighting ceremony in years, so we figured it would be a blast. Although it was an extremely cold night, the great musical performances (including one by former “American Idol” contestant Elliott Yamin) more than made up for frozen toes. I actually watched this season so it was pretty fun to see a live performance.
I was so cold, but I really loved the festive vibe. The show also included a sneak preview of “The Grinch Musical,” a sneak peek of the Boston Ballet nutcracker, and local holiday performances. I would love to check out some of these shows this Christmas season. I have always wanted to see The Nutcracker around the holidays but never got around to it. Maybe this year will be the year, finally! Update: This wasn’t the year, unfortunately. We were all setting on seeing the Boston Ballet and then Mike picked up a really nasty cold. Oh well, maybe next year!
Ice skating at America’s oldest public park
Another fun activity which I have been enjoying for many years (although I still stink) is ice skating. The Boston Common Frog Pond ice rink is the most festive place to skate in the city. Ice skating is a great cardio workout that burns plenty of calories! I love this rink because it features great views of the city in the backdrop and It’s located within easy access of restaurants and shops.
I also find it much easier to find free parking this time of year over the busy summer tourist season. That being said, there are a ton of amazing historic sites (many of which are free) which make a trek to the city worthwhile in any season.
The trees around the rink are lit up with pretty lights for the season. Also, the rink is located just a few minutes from the Boston Common Christmas tree, so now is the perfect time to visit. The rink is usually pretty crowded. I try to get out here on weekdays if possible to avoid the tourists. Either way, it’s a beautiful place to skate.
Update: Admission is $10 for adults, and free for children under 58 inches. Skate rentals are $15 for adults and $10 for kids. The rink is usually pretty crowded.
More Christmassy fun in the city
Holiday concerts and shows – See the Nutcracker or Holiday Pops at Symphony Hall.
Faneuil Hall – See the massive Christmas tree, dine, and shop in the historic marketplace referred to as “The Cradle of Liberty.”
Miracle – Enjoy a festive holiday cocktail at this popular pop up bar with locations throughout the country.
Enjoy a specialty espresso drink or hot coffee – Many local coffeehouses offers special seasonal drinks this time of year. If the setting is cozy and decorated for Christmas, then the experience is all the more special! One of my favorites is Cafe Vittoria, a charming Italian cafe located in the North End. We tried both an Americano and mocha. I usually prefer only black coffee but wow this mocha was tremendously. Seriously, the best I’ve ever tasted. They also serve gelato and other treats.
Macy’s – View the holiday tree and festive windows as the iconic department store’s Downtown Crossing location.
Also, this is a great time of the year to explore the city’s best attraction, the iconic Freedom Trail with few crowds. I love photographing all the historic sites with no crowds in the background.
Along the way, I recommend taking a break for a fabulous meal at Giacomo’s – the best Italian restaurant in the city. I love their pumpkin tortellini and Mike loves the lobster ravioli. Winter is such a great time of the year to sit down with a cozy Italian meal.
