Coast down Mass Ave toward Harvard, and you'll come across the Hong Kong (1238 Mass Ave, Cambridge, 617.864.5311), a Cambridge institution open until three on the weekends, famous for its comedy scene, its scorpion bowls, and its occasional instances of bouncers tossing misbehavers down the stairs.
The Coolidge Corner Theatre's (290 Harvard Street, Brookline, 617.734.2500) "@fter midnite" program won't keep you out all night, but it will keep you entertained with some weird-ass offerings: the cultish, the campy, the classic. And it's not just movies — on Saturday, September 18, for example, you've got "Naked Girls Reading: Science Friction." And it's exactly as it sounds: nude broads reading Ray Bradbury, Isaac Asimov, and Jules Verne.
A few choice bars offer late-night menus that are worth hanging around for. Go basic at Eastern Standard (528 Comm Ave, Boston, 617.532.9100), with a grilled-cheese or roast-beef sandwich, or class it up with a 1 am ordering of oysters, steak tartare, or artisanal cheeses. The Franklin Café (278 Shawmut Avenue, Boston, 617.350.0010), a South End stalwart, is another place to grab a plate of food long after the dinner bell rang. And for all-night non-bar food options, load up on calzones, tiramisu, and sfogliatelle at Bova's Bakery in the North End (134 Salem Street, Boston, 617.523.5601). Market in the Square (60 Church Street, Cambridge, 617.441.2000) on the corner of Church and Brattle streets in Harvard Square is a beefed-up high-end deli and convenient store which charges too much but does stay open all night. The Shaw's in Porter Square is another option when you want Duncan Hines mix and a container of olives at 4:30.
But there's more than eating and drinking. There's also general late-night mischief. While it's still warm out, Indian Summer and all that, get yourself over to Jamaica Plain, and, by the cover of night, slip off your clothes and skinny dip in Jamaica Pond. There'll be turtles and murk, and there's the exciting chance you'll be busted by the cops and have to exit the water clutching your privates, but that's in large part the fun.
How many times have you been hanging out at 5:30 in the morning and found yourself with the unfightable urge to bowl? Too many to count, we know. It's a good thing for Boston Bowl (820 Morrissey Boulevard, Boston, 617.825.3800). Pool and arcade games are on ample offer, and from 9 pm on Monday to 7 am on Tuesday morning, you can bowl half price. And to make matters more exciting, it also houses its own brewery (named, winningly, Deadwood) on the premises.
In the mischief and mystery vein, you've also got SCUL, Boston's pedal-powered chopper gang. Tall bikes! Strange missions! "An organized battalion of funk." Bold nerds on wild bicycle spaceships. No hours of operation, per se, but the superheroism of it all lends itself to the stuff of dream-time.