Holiday Traditions Old and New on Tap This Weekend

By Adam Swift

If you’re not in the holiday spirit yet, just wait until this weekend in Charlestown.

All Roads Lead to Charlestown is rekindling an old-time holiday tradition in the neighborhood with the Charlestown Christmas Stroll from 11 a.m. to 4 p.m. at the Training Fieldon Saturday. And at the historic Warren Tavern, the 34th Toys for Tots Open House runs from 4 p.m. to 8 p.m. on Sunday.

“The Christmas Stroll was a tradition when we were kids, and it is something that we wanted to bring back,” said Aileen Gorman of All Roads Lead to Charlestown, who organized the event along with Sean Boyle and Erica Walsh. “I remember when I was a child and they used to shut down Main Street and the pushcarts, they would be lined up around Charlestown, and it was just something that was very nostalgic. So we wanted to do something for the kids in the town.”

A Christmas scene as seen on the U.S.S. Constitution during one of their past tree lightings on the vessel. This year’s tree lighting is planned for Saturday, Dec. 5 at 4:30 p.m.

On Saturday, the Christmas Stroll will include about 35 vendors along with horse-drawn wagon riders, Santa’s Village with an array of walk-through Christmas inflatables, a Nativity themed petting zoo, a trackless train ride, and of course, a visit from Santa Claus followed by a tree lighting at 4 p.m.

“A big part of All Roads is supporting small businesses, and a lot of the small businesses don’t have storefronts and during the pandemic a lot of these businesses struggled in their homes to make revenue,” said Gorman. “Part of any of our events we try to support these small businesses, so the market is a big part of supporting these businesses to get their names out there.”

In addition to supporting small business, Gorman said the goal of the Christmas Stroll is to have a fun, free event for children and families.

“We want the kids from all parts of Charlestown to be able to come to our event and not worry if they have any money in their pockets to be able to come,” she said. “Through our generous sponsors we have some great entertainment and decorations and all kinds of fun stuff for the kids that they can enjoy all day long.”

Gorman said All Roads Lead to Charlestown is grateful to all the Charlestown residents who have supported the event and bought raffle tickets to help fund the Stroll. She said the winner of the $5,000 raffle will be picked by Santa at 3:30 p.m. on Saturday.

The day after the Charlestown Christmas Stroll, the Warren Tavern takes center stage with its Toys for Tots Open House on Sunday from 4 p.m. to 8 p.m.

“We’ve been doing Toys for Tots for over 34 years at the Warren Tavern,” said Kim Mahoney, the manager of the Warren Tavern. “All of the donations go directly to Charlestown families, so we ask people they can either donate an unwrapped toy or a gift card. There is a greater need for teenagers, so a gift card suits a teenager a little bit better, because sometimes they are forgotten in all of this.”

Mahoney said the tavern works closely with the John F. Kennedy Family Center to help provide the donations to the community.

Anyone who donates an unwrapped toy gets a raffle ticket for a drawing for a number of items, including an outdoor heater this year.

“Because it is an open house, we do complimentary appetizers for everyone who is attending, and it’s just a really nice, fun event that we have been doing for a long time and we’re excited that we are able to do it again this year,” said Mahoney.

The event is typically attended by a wide range of community members, from neighbors to local politicians, and Governor Charlie Baker has been known to show up in the past.

“The generosity of the Charlestown community is amazing,” said Mahoney. “The folks really go out of their way to make sure families who don’t have a lot have a great Christmas. We would not be able to do this without the generosity of the community.”

If one tree lighting is not enough, the U.S.S. Constitution will light their tree on Sunday December 5 at 4:30 p.m., the ceremony is free and open to the public, and will include refreshments, holiday music and tours of the ship.  Also, don’t miss the Annual Open Studios and the December Art Exhibit opening at The Stove Factory and Gallery, 523 Medford Street. Doors will be open Saturday the 4th and Sunday the 5th from 11a.m. to 5 p.m.

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