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Holiday Trolleys, Drone Shows and More Things to Do in Boston This Weekend with Kids

Santa Claus is coming to Boston this weekend, with stops all over New England for holiday fun! Photo courtesy of the Nantucket Chamber of Commerce
Santa Claus is coming to Boston this weekend, with stops all over New England for holiday fun! Photo courtesy of the Nantucket Chamber of Commerce
12/3/25 - By N Ferreira

Looking for the best things to do in Boston this weekend? Here are some family-friendly events and activities in the area to add to your list. 

Boston is bursting with holiday magic this weekend, offering families plenty of sparkle and cheer. The Holiday Drone Show on The Common lights up the sky with a dazzling display, the Mayor's Enchanted Trolley Tour brings music and merriment to neighborhoods across the city, and The Union Square Jingle fills the streets with festive fun. With celebrations happening all around, it’s the perfect weekend to bundle up and make some merry memories.

Make sure to tag us @mommypoppinsboston on Instagram so we can see all the fun you had!

More Things To Do in Boston This Week with Kids:

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Best Things To Do This Weekend in Boston

Nantucket Christmas Stroll

Nantucket — FREE
Friday, December 5-7
Join the island community of Nantucket and embrace the holiday spirit with one of New England's most classic (and prettiest) Christmas strolls. The 49th annual event features an illuminated tree-lined downtown, live entertainment, costumed carolers, and more.  READ MORE

Christmas at Gordon

Wenham
Friday & Saturday, December 5-6
Celebrate Christmas with friends and family at Gordon’s campus. From hot cocoa to the joyous Christmas Gala, Christmas at Gordon is everything merry and bright. READ MORE

Saint Bernards Come to Smolak Farms

North Andover — FREE
Saturday, December 6
Join the New England Saint Bernard Club at Smolak Farms for a sled pull! Families can come out and choose from our extensive selection of pre-cut trees. These lovable and gentle Saint Bernards will pull them back to your car and take pictures with families making this an unforgettable experience. READ MORE

Powisset Holiday Pig Wagon Lighting

Dover— FREE
Saturday, December 6
Powisset Farm’s popular annual Powisset Holiday Pig Wagon will return for the second year! This event features the lighting of the Powisset Holiday Pig Wagon, reflecting the long history of the beloved local farm. READ MORE

Holiday Drone Show on The Common

Boston—FREE
Saturday, December 6
Celebrate the Magic of the Season at Boston’s Holiday Drone Show. Watch the night sky come alive with dazzling drone displays every Saturday, with shows at 6:00 PM and 8:00 PM. READ MORE

Mayor's Enchanted Trolley Tour

Boston—FREE
Saturday, December 6
For the 29th year, the Mayor's Enchanted Trolley Tour will continue the festive tradition of lighting holiday trees while bringing holiday spirit to children across Boston. The event includes visits with Santa, tree lightings, and more. READ MORE

Ice Princess Party (Ages 3-10) at New England Botanic Garden

Boylston
Saturday, December 6
Join Amanda Maruco of Regal Princess Parties for a magical winter princess party. Participants are encouraged to come dressed as a winter fairy, prince, princess, or other cold weather magical being. Meet everyone’s favorite winter princess, try an icy winter craft, sing songs, read stories, and more during this magical program. Please note this class is geared toward children with their adult companions. READ MORE

Snap a Pic, With Ol' St. Nick

Harvard
Saturday, December 6
Santa will be making a special visit to the Fruitlands Museum Holiday Artisan Market on Saturday, December 6, to hear what all the little ones want in their stockings! Meet with Santa, take a picture, and browse the Artisan Market to discover unique holiday gifts. READ MORE

Gather & Glow: Chosen Family Hanukkah Party

Arlington
Saturday, December 6
Kindle new traditions and celebrate the season with community! Join fellow LGBTQ+ families for a night of connection, creativity, and light—with a latke bar, lantern making, sensory activities, and schmoozing. READ MORE

The Union Square Jingle

Somerville
Sunday, December 7
This celebration of Union Square sparkle, discovery, and delight is sure to jumpstart holiday shopping and get the whole family exploring all that the “38th coolest neighborhood in the world” has to offer!  READ MORE

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