Things to Do in the Winter

Discover the magic of wintertime in Boston and embark on a historical “Transportainment^®” adventure!

Go Ice Skating at Frog Pond

One of the most popular spots in the city to go ice-skating, Frog Pond is located within Boston Common. You can rent skates or bring your own and the café offers delicious hot cocoa to warm you up when you need a break.

Take the Old Town Trolley Tour

A great way to see all the sights, the Old Town Trolley Tour will take you to more than 100 of the city’s most popular attractions and historical sights. Along the way, you’ll be entertained by the onboard conductor and have no need to worry about finding parking around the city. Hop on and off as often as you wish and check out all that Boston has to offer.

Holiday Tree Lighting Ceremonies

If you’re visiting Boston in December, you can get into the spirit of the season by enjoying several different tree lighting ceremonies. The Boston Common ceremony takes place in early December and includes games, prizes and activities such as the lighting of the special tree that was a gift from Nova Scotia. There are also ceremonies at Copley Square and the Commonwealth Avenue Mall. Experience the sparkling lights and merriment that signifies the beginning of the holiday season in Boston.

First Night

One of the most popular events in Boston is the special New Year’s Eve celebration that takes place in several Boston neighborhoods. First Night attracts more than a million people each year and includes fireworks, live performances, a grand parade, crafts, ice sculptures and more.

Hanukkah Celebration at Faneuil Marketplace

Bring the family and enjoy music, crafts, delicious latkes, jelly doughnuts, Hanukkah gelt and games for the children. The Freedom Menorah will be lit and dedicated to the victims of the Boston Marathon bombing. Check online for the date and time of this family event.

Relive the Boston Tea Party at the Annual Reenactment

Returning in 2023 

Annually on December 16, visitors and locals gather to commemorate the fateful night that forever changed America’s history. The event begins at the Old South Meeting House as you join more than 100 re-enactors who bring the Boston Tea Party to life. You’ll march alongside the colonists to Griffin’s Wharf, dump tea overboard and learn about the Boston Tea Party and how it sparked the American Revolution.

Old Town Trolley’s Holiday Sights & Festive Nights Tour

Take in the fun and merriment of the holiday season on an Old Town Trolley Holiday Sights & Festive Nights Tour! You’ll have a front-row seat as you experience the dazzling lights and splendor of the season, riding through town as carolers fill the night air with music. Add complimentary seasonal beverages and snacks, and you’re all set for what promises to be a new holiday tradition in Beantown!