"Boston Winter" will feature a mix of winter activities. This includes an outdoor skating path and an expanded holiday shopping market. The Millennial Entertainment Group will also be producing hospitality experiences and attractions. The event will run seven days a week. For exact hours of operation, check the bottom of this page.

Berkshire Bank is the official community partner of "Boston Winter." The bank has helped bring to life year-round programming to City Hall Plaza. As part of that effort, the "Berkshire Community Stage" will return this year. Local artists and community groups will get a chance to showcase their talent.

The Main Streets Explorer is a pilot program. We're offering a shuttle on December 7, 14, and 21 between three Main Street Districts:

• Hyde Park
• Roslindale Village, and
• West Roxbury.

We want riders to experience the live music, restaurants, stores, and events in each neighborhood. Our free shuttle is open to anyone who wants to ride. It's an easy way to shop, eat, and play locally. Learn more about when and where to pick up the shuttle at the bottom of this page.

This pilot program is run by the Mayor's Office of New Urban Mechanics. Through this experiment, they are testing ways Main Street Districts could be even more welcoming spaces for all.

For the 24th 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 is sponsored by Bank of America, and includes visits with Santa, holiday performances, tree lightings and more.

On the first day of the 2019 Mayor’s Enchanted Trolley Tour, the trolley will be stopping at the following locations:

• 5:30 p.m. - Mattapan Square, Mattapan
• 6:30 p.m. - Wolcott Square, Readville
• 7:15 p.m. - Hastings Street Lot, Centre Street, West Roxbury

To learn more about the Mayor's Enchanted Trolley Tour and Tree Lightings, and view the full, three-day schedule, visit the 2019 Enchanted Trolley Tour page.

For the 24th 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 is sponsored by Bank of America, and includes visits with Santa, holiday performances, tree lightings and more.

On the second day of the 2019 Mayor’s Enchanted Trolley Tour, the trolley will be stopping at the following locations:

• 1 p.m. - Codman Square, Dorchester
• 1:45 p.m. - Hyde Square, Jamaica Plain
• 2:30 p.m. - J.P. Monument, Jamaica Plain
• 3:30 p.m. - Brigham Circle, Mission Hill
• 4:15 p.m. - Bolling Building, Roxbury
• 5:30 p.m. - Blackstone Square, South End
• 6:45 p.m. - Oak Square, Brighton

To learn more about the Mayor's Enchanted Trolley Tour and Tree Lightings, and view the full, three-day schedule, visit the 2019 Enchanted Trolley Tour page.

For the 24th 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 is sponsored by Bank of America, and includes visits with Santa, holiday performances, tree lightings and more.

On the third day of the 2019 Mayor’s Enchanted Trolley Tour, the trolley will be stopping at the following locations:

• 1 p.m. - M Street Park, South Boston
• 2 p.m. - Essex Street / Harrison Avenue, Chinatown
• 3 p.m. - Paul Revere Mall, North End
• 3:45 p.m. - Thompson Square, Charlestown
• 4:45 p.m. - Maverick Square, East Boston
• 6:30 p.m. - Adams Village, Dorchester

To learn more about the Mayor's Enchanted Trolley Tour and Tree Lightings, and view the full, three-day schedule, visit the 2019 Enchanted Trolley Tour page.

The free event will feature appearances by Mayor Walsh, NECN’s Jenny Johnson, Santa Claus, and Rudolph along with musical performances by the Boston Children’s Chorus, the Boston Pops Brass Quintet, and Berklee College of Music students Britani Washington and Sam Robbins.  

The Old South Church bell will toll when the tree is illuminated.  Light refreshments will be provided by local businesses New England Coffee, DAVIDsTEA, and HP Hood LLC. The Fairmont Copley Plaza will host a family reception immediately following for all in attendance.  The reception will include cookie decorating, photos with Santa, and treats from the Fairmont Copley Plaza.

Even more festivities will take place in and around Copley Square on November 27. The Boston Public Library and The Catered Affair will host a Storytime and Candy Cane Tea at the library from 3:30 - 5 p.m.  The tea is free but reservations are required by calling 617-859-2272. 

For additional information please call the Boston Parks and Recreation Department at 617-635-4505.  To learn more about The Friends of Copley Square, please visit www.friendsofcopleysquare.org.