Holiday Stroll & Gift Market

The 20th annual Dedham Square Holiday Stroll is a free event that kicks off the holiday season on the first Friday of December-rain or shine from 5-8pm. Get ready for exciting night of music and caroling, 50+ street vendor gift market, food vendors, and a lineup of free holiday fun including Santa, Mrs Claus and Elfie lighting the tree at 6:30pm, pictures with Santa, free activities, model train exhibit and much more! Updates are being added weekly to the Activities and Specials listing below.