20 Fun Things To Do Over Winter Break in Boston with Kids

Join the Trustees to search for snowy owls. Photo courtesy of the Trustees
Join the Trustees to search for snowy owls. Photo courtesy of the Trustees

When school takes a pause between Christmas and New Year's Day, it's nice to kick back and relax from the usual routines; but keeping kids busy over winter break can be a challenge. Thankfully, there is no shortage of fun and easy things to do around Boston during Christmas vacation week! Here are 20 enriching, socially distant activities from cooking workshops to STEM crafts and nature classes that will be sure to nip "I'm bored" in the bud.

For more things to do in Boston with kids over winter break, consult our Winter Fun Guide and our holiday guide. Plan to have a great time with your kids during the upcoming, and much-needed, school break. 

In-Person Winter Break Activities

The Painting Place in Wellesley is open for in-person workshops, drop-in crafts, or takeout projects. 

Winter Workshops at The Painting Place—Wellesley

Weekdays December 20-31, 2021
Sign up for a single day workshop (9 am-12 pm, with additional time optional) or multiple days and do a variety of painting projects, crafts, and games. There will also be outside play opportunities during snack and game time, weather permitting. Sign up for workshops on the website.

Reindeer Quest in Bird Park—Walpole

Free - Daily through January 2, 2022
Find 4 wooden reindeer sculptures—Charlie, Anna, Billy, and Birdy—hidden in Bird Park. Pick up a bell at the Bird Park Office and put it around the neck of the first reindeer you spot on this self-guided, free tour, available dawn to dusk.

Snowy Owl Prowl—Ipswich

Saturdays and Sundays in December and January, February, and March 2022 along with weekdays February 21-25, 2022
Join the Trustees to hike in the dunes in search of these magnificent birds. 

Drop-off nature programs are available during winter vacation at Puddlestompers. 

Puddlestompers Nature Vacation Programs—Newton and Wellesley

December 20-23 and December 27-31, 2021
Kids ages 4 to 7 will explore wintry nature habitats and play outside together during this drop-off program. Sign up kids for a session that begins at 9am and ends at 1pm, or sign up for multiple days, depending on availability.

There are many of the area's long-cherished light displays gracing ZooLights. Photo courtesy of the Stone Zoo

ZooLights at the Stone Zoo—Stoneham

Most days through January 9
For those who had trouble getting tickets before Christmas, ZooLights will stay aglow through January 9. Take the whole family for this magical tour of lights on a winding illuminated path full of enchanting lights and exotic animals. Reserve tickets online.

Private Cookie Decorating Classes at Smolak Farm—North Andover

Offered most days throughout December 2021
Book a private cookie baking and decorating workshop at Smolak Farm with a minimum of 7 family members or friends in your pod. Chefs teach the class and provide supplies for each baker to decorate six cookies. Smolak Farm also hosts many other holiday activities, including storytime with an elf and gingerbread house workshops. 

Masks are required at a winter vacation kids' cooking class at Powisset Farm, but the smiles will definitely still be on their faces.

Kiddos in the Kitchen at Powisset Farm—Dover

December 11, 2021
In this kids-oriented cooking class, children decorate holiday cookies. The farm is also hosting a free Reindeer Quest self-guided program from December 2021 through the end of January 2022.

Winter Lights—Canton, North Andover, or Stockbridge

Wednesdays to Sundays through January 8, 2022 
The gardens at the Bradley Estate, the Stevens-Coolidge House and Gardens, and Naumkeag are made even more magnificent at sundown with sparkly lights.

Castle Hill is enchanting day or night. Photo courtesy of The Trustees

Christmas at Castle Hill—Ipswich

Select days December 2021-January 2022
Come check out the decked halls and unique rooms at Castle Hill. This year's theme is the Roaring Twenties. 

Southwick Zoo Drive-Thru Winter Wonderland—Mendon

Wednesdays to Sundays through January 2, 2022
Drive through the Frozen Forest, cruise through Whoville, and have a meet and greet with Santa. Enjoy a cup of hot cocoa or delicious s'mores to warm up.

New Year's Eve Party with Cinderella—Billerica

December 31, 2021
Ring in the New Year at this afternoon party. Dress up, get a sparkly manicure, fancy hair updo, and enjoy fun and games and countdown to 2022 with Cinderella and Sugar Plum Parties.

Build and decorate clay folklore dolls at an outdoor workshop on December 31 at the deCordova Museum. Photo courtesy of the Trustees

New Year's Folklore Dolls Workshop—Lincoln

December 31, 2021
At this outdoor workshop, you can create "folklore-styled" dolls that will be fired and ready to take home as a holiday decoration. Children and families are welcome, and there will be hot cocoa and cider to keep warm.

Neighborhood Light Tour—Various locations

If your kiddies are really digging the sparkly lights, take a family drive to see some of the most elaborate holiday lights on houses in Boston area neighborhoods. 

Outdoor Ice Skating—Various locations

Enjoy several Boston-area outdoor ice skating rinks, including a reopened Boston Common Frog Pond, for a fresh-air spin.

Winter Day Trip—Various locations

See our ideas for spots that offer fun kids' winter activities, from Canton to Carlisle.

Snow Tubing—Various locations

It might be hard to fly away for a vacation, but tubing parks within 1 to 3 hours of Boston are open (and making snow) for downhill thrills.

Try some candy engineering at the Metropolitan Waterworks Museum. Photo courtesy of the museum

Candy Engineering Workshop—Boston

December 29-30, 2021
Kids (ages 4 and up are recommended) will design a candy maze and experiment with different spice drop structures at the Waterworks Museum. The museum recommends a $5 donation to attend.

The Boston Ballet Nutcracker—Boston

Now through December 26, 2021
This treasured classic is back on the big stage to make this holiday season bright. Join Clara, Uncle Drosselmeyer, the Mouse King, and all of the cast at the Boston Ballet.

Virtual Winter Break Activities 

Story Pirates Sleep Squad Show

Purchase and stream online
Having trouble winding the kids down after all the holiday fun? The award-winning sketch comedy troupe offers a new kind of bedtime ritual for kids ages 4-12, in which the "Dream Queen" guides kids through 3 different enchanting audio experiences, adapted in classic Story Pirates fashion from stories written by real kids. Purchasers determine their personal start date and then have 4 weeks to experience the show with unlimited views. You can also opt to buy a “Dreamtime Travel Kit” which is delivered to each family’s home address within 2 weeks of purchase. 

Online Storytime at the Boston Public Library

Multiple dates
The Boston Public Library (BPL) hosts a vast array of terrific events, both online and in-person. From Facebook Live's story time and crafts to Tween Time on Zoom, the BPL has families covered during the holidays to keep enrichment and learning happening.



Nantucket Christmas Stroll
Nantucket - 10:00 AM Pick
Holiday Happenings at Suffolk Downs
The Track at Suffolk Downs - 10:00 AM Pick
Sweets and Treats for the Holidays
Copper Mill Hall at Paul Revere Heritage Site - 10:00 AM Pick
Saint Bernards Come to Smolak Farms
Smolak Farms - 10:00 AM Pick
Neighborhood Guides
Activity Guides