The annual Beacon Hill Holiday Stroll unites Charles Street merchants who collectively open their doors for one festive afternoon each December, but the beloved holiday tradition can actually be traced back to the efforts of Upstairs Downstairs Antiques.
In the early ‘90s, the Charles Street antiques store held an annual open house in December, inviting customers and fellow business owners to join them for an evening replete with wine and hors d’oeuvres.
“It was a rather small, festive gathering in appreciation of our customers and neighboring businesses, with no intent at all on selling anything,” wrote Rebecca Connolly Hackler, who co-owned the store with Lauren Decatur at the time. “In fact, if someone wanted to buy something during the party, it would be strange! We’d simply set the item aside, and they’d come back another day for it.”
By the mid ‘90s, Upstairs Downstairs joined together with some neighboring shops (specifically Carol White Sullivan at Hyacinths, Doug Spain of Churchill Galleries, and Jack Bone and Michael Riendeau of Antiques at 99), according to Hackler. At this time, other Charles Street merchants proposed to Hackler and Decatur that rather that Upstairs Downstairs Antiques hosting a solo open house, neighboring businesses could band together and collectively hold an open house for the holidays instead.
By 1996-1997, the effort became much more organized with the help of the Beacon Hill Antique Dealers Association and carolers and Santa Claus were hired for the occasion. Pedestrian traffic during what became known as the Beacon Hill Holiday Stroll became so congested that Charles Street was eventually closed to vehicles and Santa arrived by horse and buggy.
More businesses joined the effort each year, Hackler wrote, and by 1998, it fell under the umbrella of the Beacon Hill Business Association and become an organized event featuring ads, poster and a program of events.
The Stroll was moved to Sunday afternoon in 2001 because the traffic on the night strolls was becoming a problem, and daytime was deemed to be more family friendly.
A Charles Street storefront decorating contest began in the ‘90s as part of the Stroll, Hackler added.
Meanwhile, in recent years, the Joint Charles Street Committee – a collaboration between the Civic Association and the Beacon Hill Business Association – has undertaken a similar effort today with its annual Holiday Storefront Decorating Contest.