Weekend Picks – December 6th

Enchanted Trolley Tour and Christmas Tree Lighting

Boston’s beloved holiday tradition, the Mayor’s Enchanted Trolley Tour, is making its way through the city for its 28th year! This magical event brings festive cheer to neighborhoods across Boston with tree lightings, visits from Santa, and plenty of holiday spirit. Sponsored by Bank of America, the trolley tour will spread joy over two days, starting on Saturday, December 7, and wrapping up on Sunday, December 8. Each stop features a holiday tree lighting ceremony complete with hot chocolate, and it’s the perfect chance to come together with family, friends, and neighbors to celebrate the season. The Enchanted Trolley will be making a festive stop at Maverick Square on Sunday, December 8 at 6:15pm. Don’t miss your chance to see Santa, enjoy some holiday magic, and witness the lighting of East Boston’s holiday tree.

Eastie Elves Toy Drive

Donate a new and unwrapped toy to the Eastie Elves Toy Drive through December 12th.  Check out the drop-off locations here! 

Brunch in the Neighborhood

From savory meals to sweet surprises (and much-needed hair of the dog), there’s something for everyone! Whether you’re in the mood for comfort food or a morning cocktail, East Boston’s brunch scene has you covered. Check out some of our favorite spots in East Boston for brunch!

East Boston Winter Market!

This weekend, December 7th and 8th, the East Boston Winter Market is bringing the community together for a festive celebration you won’t want to miss. Hosted at Tea by the Sea – Overseas Student Services, the market is packed with holiday cheer. From unique gifts by local vendors to a FREE hot chocolate bar (yes, free!), and delicious treats like buñuelos and natilla, there’s something for everyone. A live violin performance will set the perfect holiday mood, and you can even snap a photo by a stunningly decorated Christmas tree. This event is more than shopping—it’s about celebrating East Boston’s multicultural charm. So grab your family, friends, and neighbors and head over to support local businesses and make magical memories this holiday season! You can learn more here. 

Brunch with Santa

Don’t miss Brunch with Santa at Pazza on Porter on Dec 7 from 12-2 PM—bring the whole family for a festive afternoon of holiday cheer, delicious bites, and fun for everyone!

Holiday Wreath Sale

The Eagle Hill Civic Association is hosting a Holiday Wreath Sale on Saturday, December 7th from 12pm-1:30pm at the East Boston High School Parking Lot. Stop by and pick one up!

East Boston Main Streets Tree Lighting

Join the East Boston Main Streets for the Annual Christmas Tree Lighting in Maverick Square on Sunday, December 8th, from 4:00 PM to 8:00 PM. This beloved tradition is packed with festive fun: 🎶 enjoy DJ music and live singing, 🎁 shop from local vendors, and soak in the festive vibes. Additionally, the Mayor’s Enchanted Trolley Tour will be in the area at 6:15 PM, bringing more holiday cheer to Maverick Square.

Jingle All the Way 5K in the Seaport

The Jingle All The Way 5K is back and coming to Boston’s Seaport! So, dig out your ugly sweaters, winter hats, and running shoes and join us on Saturday, December 7th for a holly jolly 5K. Post-race we’ll be sure to have a festive post-race celebration with live music, delicious food, and amazing drinks. Wearing your favorite holiday outfit is also strongly encouraged as we will be rewarding some of the best-dressed runners!  You can learn more here. 

East Boston Sunset Rave

Come one come all to a sunset rave in a surreal field in East Boston on Saturday DJ’ed by the one and only Gid, DJ GiddyBee. Bring your homies, dress warm, wear rain boots, byob and leave no trace 😏🤞 The party will follow an opening at 2pm to celebrate local artist Anja’s Experiments new art installation.

Get out there, Eastie, and make this weekend a festive one! Let us know what you’re up to by tagging @CaughtInEastie on Instagram. 🎄✨