The Vibe: Built in 1954, the Wallingford neighborhood location is the earliest outpost of the quintessential drive-in chain. Loyalists of all ages come for drive-in classics like fresh burgers, hand-whipped shakes, and house-cut fries; in fact, that’s pretty much all that’s on the menu. There’s no customer seating, so in-car dining is part of the experience.
The Crowd: Burger snobs and toddlers find common ground at this award-winning (local publications have cited Dick’s for its Best Cheap Eats, Best Burger, Best Fast Food, Best Fries...the list goes on), kitschy kitchen.
Time-Travel Tip: Don’t try to ask for substitutions or omissions; the as-is attitude is part of the tradition.
Santa Cruz, CA: The Beach Boardwalk
The Vibe: The 1907-founded boardwalk offers quintessential family fun on turn-of-the-century rides like the carousel, dating from 1911, and the Giant Dipper, from 1924. Even the modern amusements are classics: a haunted house, flume, and roller coasters.
The Crowd: Giant, roving reunion groups, weekend family outings, and stress-busting USCS students stroll the sunny strip.
Time-Travel Tip: Catch one of the late nights, when the rides close at 11 p.m., for all the joys of the park without any of the tantrums. Check the website for scheduling, as closing times vary greatly weekend to weekend.
The Vibe: The lanes at this hipster hangout were salvaged from an old Ohio bowling alley. The midwestern anyman feel of the bar is accentuated by 1970s scoring machines and classic Tiffany-style lamps.
The Crowd: Barflies and bowlers are a steady mix of American Apparel–clad Williamsburg wannabes, ironic vintage-bowling-shirt-sporting cool kids, and interlopers from other boroughs.
Time-Travel Tip: Show up before 8 p.m. Monday through Friday for $6 games and a dollar off drafts and well drinks. While the bar stocks more than 12 beers on tap, food options are grim (a vending machine), so fuel up pre-frame.
Seabrook, TX: Keels & Wheels Concours D’Elegance
The Vibe: This is not the place for bikini-clad car models. The genteel annual showcase (it may be in Texas, but it’s still a yacht club) attracts 200 classic and exotic cars as well as 60 vintage wooden boats. This year’s gem: the 1920s Pierce-Arrow used in the movie Smokey and the Bandit and owned by the movie’s star, Burt Reynolds.
The Crowd: Older car-enthusiasts and their grandchildren (children under 10 get in free) dominate the scene. While some chaperones may have driven the 1920s specimens, the kids will enjoy the public unveiling of the WaterCar. The amphibious vehicle reaches speeds of 125 mph on land and 45 on water.
Time-Travel Tip: Stroll the nearby Kemah boardwalk—just across the lake—for amusement rides, arcade games, restaurants, and shopping, or stick around to bid on one of the cars during the auto auction.
Fairmont Hotels & Resorts
The Vibe: Gidget goes Hawaiian at this indoor tiki space. The lounge offers dinner (Pacific Rim cuisine, of course) and a show, but the only show you really need is the— brace yourself—indoor rainstorm.
The Crowd: Young professionals with a penchant for the tacky saddle up to the bamboo bar for killer mai tais.
Time-Travel Tip: On Thursdays and Fridays, the bar has an all-you-can-eat buffet, along with happy-hour cocktail prices.
The Vibe: The Harlem Renaissance is alive and well at this iconic 1934 establishment. Wednesdays have been reserved for new talent for almost 80 years, during which the talent show discovered the likes of Ella Fitzgerald, Billie Holiday, Jackie Wilson, and The Isley Brothers.
The Crowd: Organizers encourage family-friendly acts like magicians, roller skaters, and animal trainers. Still, the seats are full of old neighborhood fixtures who come for the tradition and young Harlem tastemakers looking for the next big thing.
Time-Travel Tip: For fans with vertigo or a fear of heights, avoid the balcony—the seating is surprisingly steep.
Jeff Hutchens/Getty Images
Towson, MD: Skateland Roller Rink
The Vibe: Old-school disco, R&B, and hip-hop augment 1970s funk at this four-wheeled roller-dancing mecca.
The Crowd: The rink has nights for each generation to make sure the skaters who came of age in the '70s are just as happy as those who think Xanadu is a Broadway classic. On Saturdays, 21-and-over nights last until 2 a.m. (as late as 4 a.m. on the first Saturday of the month). A strictly over-30 crowd takes to the hardwood every Wednesday night.
Time-Travel Tip: Tuesday-night admission is a mere $3 for three hours (other nights are a steep $5 or $10).
Courtesy of Century Ballroom
The Vibe: Get your dance cards ready and take to the 2,000-square-foot floor for an evening of salsa or classic ballroom, or just gawk from the balcony. The venue offers weekly dance classes as well as lesson-and-dance combo nights.
The Crowd: Ideal for date night, the mostly-coupled crowd is an eclectic cross between Singin’ in the Rain baby boomers and Dirty Dancing–raised Gen Xers. Clothing is just as varied, with jeans and T-shirts Lindy Hopping next to cocktail attire.
Time-Travel Tip: Make it an evening by having dinner at the Tin Table, adjacent to the dance hall. When calling for a reservation, request to be seated in the ballroom. January and February mark the cabaret season, when guests can see a show over dinner and cap the evening with dancing.
The Vibe: Equal parts 1980s gritty punk and 1940s fishnetted pinup, the competitors here always provide a raucous spectacle. Skaters like Apocalyptica and Krissy Krash bring out the best (and the costumes) of the fans.
The Crowd: L.A.’s edgy 20-somethings come out for the booze and brawls. The occasional celebrity will join the spectators, but the packed venue isn’t much for coiffed clubbers.
Time-Travel Tip: Bring money (the ATM has high surcharge fees) for the cash bar and famous hot-dog-on-a-stick truck. And buy your tickets in advance—but skip the VIP option in favor of standing room, closer to the action.