Nostalgia-cation

1950s
The menu at Ellen's Stardust Diner (1650 Broadway at 51st St; 212-956-5151, ellensstardustdiner.com) tells you that the average rent in 1950 ($75) was not much more than what you'll pay for a meal for two at this charmingly touristy restaurant ($50). But with Ellen's waitstaff crooning retro melodies in your ear, it's easier to justify (particularly when your meal is washed down with an egg cream or malted). Complete your journey back in time by hopping aboard the New York Transit Museum Nostalgia Train trips. A wicker-lined car chugs to Coney Island on July 23 and another to Rockaway Park on August 20 (718-694-1600, mta.info/museum; 10am--5pm; $20--$50).

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1980s
Whether you were the head cheerleader in high school or the head nerd, attempt to right your teenage wrongs (or just relive them) at the, like, totally interactive Awesome 80s Prom (Webster Hall, 125 E 11th St between Third and Fourth Aves; 877-RAD-PROM, awesome80sprom.com; Sat 8pm; $55--$100). Only this time you won't need to sneak a beer in the limo ahead of time. If your dance moves look hotter at five miles per hour, the (Good Units, 356 W 58th St between Eighth and Ninth Aves; downandderby.org; Fri 17 9pm--4am; $10, with R.S.V.P. $5) is a bimonthly skating-boozing event where the drinks are cheap, the tunes are old-school, and knee-high socks and striped short shorts are encouraged. Skate rentals are limited, so arrive early or bring your own.

1990s
Bond with other fans of cult-classic television shows at Secret Formula's TV parties (secretformulany.tumblr.com), with themed cocktails, rare footage and clips, live music and one-of-a-kind contests (past events have featured Bill Haverchuck look-alike competitions). Michael Austin and Secret Formula's group sing-alongs are centered on everything from specific decades ('80s, '90s) to movies (The Lion King and The Little Mermaid, plus other, non-Disney flicks). If neither of those blowouts gets you feeling sufficiently smug about your '90s know-how, make plans to compete at one of five TV trivia events hosted by Trivia A.D. (triviaad.com) each month.