Your Guide to Boston’s Best Holiday Experiences

As the holiday season kicks off, many people in the Greater Boston area seek festive, immersive activities to attend with family and friends. While perfect for embracing colder weather and holiday spirit, some of these limited-time opportunities are often lesser-known to the public. Some noteworthy examples of these events include: the Snowport in Boston, the Festival of Trees in Wellesley, ice skating on the Boston Common Frog Pond, and the Magic of Lights Drive-Through Show in Foxboro.

Although several of these events may not be the most frequent topics of discussion, one of the more familiar opportunities that is held in this area is Snowport, a festival located in Boston’s Seaport region. Snowport features 125+ pop-ups of all sorts, including holiday shopping, food trucks and vendors, art shops, novelty item booths, hot chocolate, and delicious waffles that you have to try! This festival is held seven days a week from November 7th-December 28th this year. Snowport’s popularity truly speaks for itself; and be prepared - on a typical day, you can expect up to a 30-minute wait time in the line to get into the festival. Monday-Thursday, snowport opens at 3pm and is least crowded between 3pm and 5pm. On weekends, for a shorter wait, the best time is right when it opens at 11:00am.

Beyond the more obvious choices for high school students, the Boston area has numerous other seasonal experiences to enjoy - one of them being the family-oriented, well-decorated, interactive Festival of Trees in Wellesley. This festive event is held from November 28th to December 28th, giving you a full month to explore. With themed holiday trees, garden lightscapes, and snow village trains, there’s something for everyone! Plus, if you enjoy raffles, you can enter for a chance to win a specially designed tree by submitting a ticket for the tree you are interested in. 

Those who seek a timeless, more active outdoor activity will find delight in ice skating on the Boston Common Frog Pond. Skaters may purchase tickets and skate for fun generally between 10:00 am and 9:00-10:00 pm, with the exception of an early 3:45 pm closure on Mondays. Additionally, the pond hosts Learn to Skate lessons around early December to mid-February; registration is required. This year, on New Year’s Eve, visitors of the Frog Pond can observe the annually-held Frog Pond Skating Spectacular: a free performance showcasing the talents of competitive figure skaters, both local and international. There are two shows and both run for about an hour. The first show starts at 3:30pm and the second one starts at 5:30. Also, there are fireworks over the Boston Common at the end of the show! Needless to say, this popular scenic city location helps promote immersion and outdoor fun every year.   

But, if staying cozy in your car while enjoying holiday magic sounds more appealing, you won't want to miss Magic of Lights at Gillette Stadium, returning for the last time ever from 5 p.m. until 10 p.m. from November 18th through December 31st. This dazzling drive-through features nearly a million sparkling lights, including the 200-foot Enchanting Tunnel of Lights, Candy Cane Lane, life-sized dinosaurs celebrating the season, and even a 32-foot animated Barbie. With festive displays accompanied by holiday tunes, Magic of Lights is an extraordinary experience for the whole family. Also, if you are planning on going on this magical light-filled adventure, be sure to purchase tickets in advance, as they will not be available at the gate.

From festive-pop ups and holiday trees to skating and remarkable light displays, Boston and its surrounding towns offer something for everyone this holiday season. Whether you’re out exploring or enjoying the magic from your car, these events are the perfect way to celebrate, create memories, and soak up the season’s cheer. Beyond simply enjoying the sights and activities, attending these seasonal events is also a wonderful way to support local businesses and community organizations that make the holidays brighter for everyone.