Party Earth Review Although Upstairs on the Square is only a few steps above Winthrop Square, its cupcake pink walls, gold chandeliers, and endless fresh flowers transport patrons far from the college town below. After ascending the leopard... ... read full review
91 Winthrop Street
Boston, MA 02138
Red Line: Harvard
Cambridge / Somerville, Boston –
Although Upstairs on the Square is only a few steps above Winthrop Square, its cupcake pink walls, gold chandeliers, and endless fresh flowers transport patrons far from the college town below.
After ascending the leopard-striped staircase, preppy grad students and sophisticated professionals unwind with a fancy cocktail or glass of wine in the Monday Club Bar, a casual space full of natural light and red-green patterned walls that owners describe as “bad girl plaid.”
Sunday brunch is particularly popular in the adjoining Zebra Room, where groups of poised girlfriends with mimosas in hand can people-watch out the oval picture windows as they devour brioche French toast or pasta with Maine crab.
A flight of stairs leads up to the airy Soirée dining room, whose pink tablecloths, mirrored ceilings, and facing fireplaces are reminiscent of 1920s sophistication. The space is a favorite for fancy affairs like bridal parties, romantic dates, and breaking up with the boyfriend, since he’d feel really awkward making a scene in such a refined place.
Popular afternoon tea time on the weekends sees patrons innocently enjoying their cup with praline chocolates and cheesy gruyere, or not so innocently with a side of champagne or spiked hot chocolate.
Habitually mellow, the bar sees the normal swell on weekend evenings, but clears out relatively early as most guests make it their first stop of the night.
The epitome of feminine elegance, Upstairs on the Square makes guests feel like the pampered upper crust.
If you’re tired of mindlessly bobbing your head to Top 40, head to Upstairs on the Square on the last Thursday of each month for a much more cultured dance experience. You’ll swear you’ve been transported back in time as you swing to big band classics played by the Bo Winniker brass band.
Harvard grad students, romantic couples, Cambridge professionals, students looking for a more sophisticated night out, and girly girls having an intimate outing with friends, mid 20s to late 30s.
Ambient jazz, classical, and big band favorites. Live band the last Thursday of each month.
Upscale American menu with an emphasis on seasonal and local ingredients such as oysters, burgers, octopus, and salmon, as well as desserts like signature chocolate-covered pecan turtles, butterscotch pudding, and churros. Valet available from 5pm M–Sa and noon Su.
Appetizers $9–$17, entrées $12–$42, desserts $6–$8. Beer $5–$7, wine $9–$14/glass or $36–$80+/bottle, cocktails $10–$13. Valet $14.
Preppy: dark jeans, conservative cardigans, blazers, polo shirts, khakis, vintage jewelry, flats, designer attire.
Friday and Saturday nights to clink glasses with Cambridge’s classy set, weekends to sip some proper tea, or Sundays for brunch to nurse mimosas and bask by the sunny windows.
Noir (Charles Hotel, 1 Bennett Street) is a vibrant nightspot that exudes a smoky 1940s atmosphere befitting its evocative name.