Upstairs at the Pudding/Upstairs on the Square


1982 – present


10 Holyoke Street / 91 Winthrop Street


Hip and spirited upscale restaurant and bar




Upstairs at the Pudding was the first incarnation of the now-thriving Upstairs on the Square, both run by longtime friends Mary-Catherine Diebel and Deborah Hughes. The Pudding was a restaurant atop the legendary Harvard Hasty Pudding Theatre, with an adventurous classic European menu in the early years of Boston's culinary revolution. Rooftop-garden dining during the summer was part of its charm. The slightly outrageous décor is part of the charm of today's Upstairs on the Square - a pink, plush, shimmery, and textural set of rooms replete with zebra print, chandeliers and a fireplace - a sort of harmonious glam - sets an escapist, festive mood. The cuisine has continued to be shaped by award-winning chefs such as Boston's Susan Regis.

Photo by Rain Robertson