Things to do in Boston this Weekend of December 8 include Holiday Trolley, Somerville Illuminations & More!

Things to do in Boston this Weekend of December 8 include Holiday Trolley, Somerville Illuminations and more!

Our picks for fun things to do in Boston this weekend of December 8 – December 10 include the Holiday Trolley, Somerville Illuminations 2023, Downtown Boston Holiday Market, SoWa Sundays & SoWa Artists Guild Winter Festival, and more!

For a complete list of fun events in the Greater Boston area check out the Localite Boston Calendar!

There’s always lots going on in Boston in terms of events and activities. There are fun things to do in Boston for adults and also Things to do in Boston with family. Our weekly round-up brings you the best things to do in Boston this weekend.

Editor’s Note: Our staff makes every effort to bring you the latest updates on activities, entertainment, food, and drink specials in the Greater Boston area. However, all information is subject to change by the organizers. As always, please confirm before you make your plans!

Also, check out our articles on Chinese Food Boston, Best Nail Salons in Boston, Flea Market Boston Massachusetts, Best Parks In Boston, and Outdoor Activities Boston!

Things to do in Boston this weekend of December 8, 2023 – Friday

Laughing Through The Pain

Are you the type to deal with your pains and stresses through humor? Well, you’ll fit right in here.

Head over to The Foundry and laugh through the pain. Let these amazingly talented comedians tickle your funny bone with dark humor.

You’re in for a night of gut-busting laughter as you’re taken on a rollercoaster ride of comedy tackling taboo topics with charm and wit.

Ira Claybourne, Steph Dalwin, Liz Dufresne, Kristina Feliciano, Emily Goldstein, Amber Malone, Erzhena Soktoeva, and Brisa Sylvestre will take the stage to give you the time of your lives!

When: Friday, December 8, 2023, 6:30 am – 7:30 pm
Where: The Foundry, 101 Rogers St, Cambridge, MA 02142 
How much: $17

Downtown Boston Holiday Market

Downtown Boston Holiday Market

Image credit: Downtown Boston Facebook

Get your Christmas gifts right in the heart of Downtown Crossing! Downtown Boston has curated a lineup of artisan vendors who offer awesome handcrafted products.

Expect a rotation of diverse vendors! You’ll find everything you’ll need, whether it’s for a family member, friend, or coworker.

When: Friday, December 8, 2023, 11 am | Fridays & Saturdays until December 23, 2023
Where: Summer Street Plaza, 10 Summer Street, Boston, MA 02110
How much: Free

Cozy Holiday Market

With Christmas right around the corner, holiday markets are popping up left and right! This one in East Somerville is one of the best ones to visit!

As you explore a variety of artisans, materials, charming products, and other winter items, sip on a warm drink. Now, that’s a nice cozy night outdoors.

Santa will even be there! So, unearth your ugliest holiday sweater and take a fun photo with him.

When: Friday, December 8, 2023, 5 pm – 8 pm
Where: East Somerville, 15 Garfield Ave, Somerville, MA 02145
How much: Free

Candle Making Workshop

There’s something so fun and fulfilling about learning a skill and making something with it.

Make your way to The Studio by Garden Streets and learn all about the art of candle making. You’ll get to practice making your soy wax candles with deliciously scented essential oils, glass jars, and gorgeous natural decorations.

You can proudly place them in your home or gift them to somebody this holiday season.

When: Friday, December 8, 2023, 6 pm – 7:30 pm
Where: The Studio by Garden Streets, 100 Cambridgeside Pl 2nd floor, Cambridge, MA 02141
How much: $65

Somerville Illuminations 2023

Things to do in Boston this Weekend of December 8 include Holiday Trolley, Somerville Illuminations & More!

Image credit: Somerville Arts Council Facebook

The stunning twinkling lights are some of the best parts of the Christmas season– and Somerville is going to be decked out in them.

The residents went all out and decked out their yards and spaces in dazzling lights, incredible ornaments, and shrines of devotion and fantasy. So, celebrate their artistry and creativity, and check out this year’s interactive Illuminations extravaganza!

When: Friday, December 8, 2023, 6 pm – 10 pm | Until early January 2024
Where: Buildings around Somerville, Massachusetts
How much: Free

Park-9 Ugly Sweater Party

Among the best and silliest holiday traditions is to don an ugly holiday sweater. Well, Park-9 is inviting you to a Ugly Sweater Party!

And the best part? Your furry babies can join in on the fun too! So, find the best sweater (you can even match!) and head over to Park-9 to have a bark-tastic time.

When: Friday, December 8, 2023, 6 pm – 10 pm
Where: Park-9 Dog Bar, 48 Waters Ave #1, Everett, MA 02149
How much: Free

Deal Alert – Enjoy the lowest price guaranteed on the very popular Boston Whale Watching Cruise

Boston Whale Watching Tour

Experience the best of New England’s marine wildlife on this guided whale-watching cruise around the Stellwagen Bank National Marine Sanctuary. Hop on a high-speed catamaran that gets to and from the whales in the least amount of time possible. See humpback and fin whales, plus Atlantic white-sided dolphins with the help of a naturalist guide. The on-board galley offers food and beverages for purchase during the trip.

Find out more and book your Boston Whale Watching Cruise TODAY!!!

Things to do in Boston this Weekend of December 9, 2023 – Things to do in Boston on Saturday

Natural Wreath-Making Workshop

Add something personal to your Christmas decorations this year. Join the natural wreath-making workshop and create a one-of-a-kind piece of decor.

The people at Appleton Farms will teach a simple technique for making these festive pieces with a variety of textural evergreen boughs foraged from the property. Then, let your imagination run wild as you decorate it with various natural ingredients, like berries, pinecones, and dried forage.

When:  Saturday, December 9, 2023, Various times between 10 am – 3:30 pm | Until December 10, 2023
Where: Appleton Farms, 219 County Rd, Ipswich, MA 01938
How much: Trustees member: $60; non-member: $75

Holiday Trolley

Things to do in Boston this weekend

Image credit: The Good Witch of Salem Facebook

Hop on the Holiday Trolley and help The Good Witch of Salem find the Gingerbread Man!

The quest will start at the shop with a story about the elusive character. Take part and interact with the story through motions, props, and baking tools. You’ll also learn how gingerbread cookies are made. But one will come alive and run off into the street! Then, race through downtown Salem in search of him!

Aside from going on a searching adventure, there will be music, instruments, dancing, and lots of surprises!

When:  Saturday, December 9, 2023, 10:30 am – 2:30 pm
Where: The Good Witch of Salem, 2 North St, Salem, MA 01970
How much: $38 – $54

List Your Event On The Localite Boston Calendar For FREE!


Event Listing in Boston

We have now enabled the Community Event Submission feature on our website. You can submit your event for Free and assuming it is appropriate for our audience, your event will get listed on our calendar – for FREE!

Check out our Event Listing Page and submit your event TODAY!!!

Boston Events this Weekend of December 8, 2023 – Sunday

SoWa Sundays & SoWa Artists Guild Winter Festival

Things to do in Boston this Weekend of December 8 include Holiday Trolley, Somerville Illuminations & More!

Image credit: SOWA Artists Guild Facebook

Head over to Art Heaven, 450 Harrison Ave, for SoWa Sunday. Meet artists and be the first to see new works. Walk the street to see plenty of vendors that can cater to your art and design needs.

It’s also the SoW Artists Guild Winter Festival! So, it’s the perfect place to get some holiday shopping done.

When:  Sunday, December 10, 2023, 10 am – 7 pm | Until December 17, 2023
Where: SoWa Artists Guild, 450 Harrison Ave, Boston, MA 02118

Holiday Charity Ice Baths

Take an ice bath and help those in need.

Ice Bath Boston coaches will prepare and coach you the whole way. But you won’t slip into icy cold water. You can compete against yourself or with a friend! See how long you can safely stay in.

Choose your pledge: $, $10, or $25 for every minute you stay in. You’ll also get to pick which charity you want your donation to go to: The Greater Boston Food Bank, Rosie’s Plae, UNICEF, or Squash Dreamers.

After the bath, socialize! Enjoy the holiday bazaar of local small businesses, live music, warm beverages, and healthy snacks.

Seasoned veterans and first-timers are welcome to join!

When:  Sunday, December 10, 2023, 10 am – 2 pm
Cambridge Athletic Club, 215 First St, Cambridge, MA 02142
How much: 
$5 -$25 per minute

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