Harvard Square: The Sinclair
It was especially hard to choose a single outdoor dining spot in Harvard Square; the alfresco hideaways at Russell House Tavern and Harvest both merit a mention, and the rooftop at Daedalus has been a high-flying mainstay for years. But this year we have to give a standing O to the roof deck at The Sinclair, which lures Harvard Square hipsters and music lovers for dinner and a drink before hitting a concert at the restaurant's adjacent nightclub component. Plus now there's an even newer reason to visit: this month the restaurant unveiled a newly redesigned upstairs bar, dubbed the Club Car, a cool eight-seater steps away from the roof deck. The Club Car is designed to look like an art deco-era train depot watering hole, with design elements inspired by vintage rail ties, an antique train-signal switchboard and photograph installations that evoke picture perfect glimpses of an "American landscape" whirring by.
52 Church St., Cambridge; 617-547-5200