For a budget-friendly sampling of retro family fun, rent a station wagon and head to the North Fork, where humble motels are plentiful and the activities are delightfully nostalgic. Plan your trip post–Memorial Day to assure open restaurants and beach-worthy weather.
1. If you’re heading out in mid-June, make a pit stop at Riverhead’s 96-acre Splish Splash water park (631-727-3600). Appreciate the relative calm of the “Lazy River,” or withstand gruesome lines with local day-campers for a ride on the 80-foot “Cliff Diver” slide.
2. Dry off and drive 40 minutes to Greenport’s resortlike Silver Sands Motel (Dirty Dancing meets The Flamingo Kid; from $150; 631-477-0011). Rent a cottage on the beach for scenic views of Shelter Island and easy access to swimming and sailing come morning. For dinner, it’s Dungeness-crab legs ($14.95) and baked stuffed clams ($6.95) at Crabby Jerry’s clam shack (above) on the Main Street wharf (631-477-8252).
3. Hit the turf Saturday at the Drossos Motel’s low-concept (think windmills) 18-hole Tick Tock Miniature Golf course (631-477-1334). Don’t miss the on-site frozen-custard stand.
4. Drive twenty minutes southwest to New Suffolk, where the folks at Captain Marty’s Fishing Station (631-734-6852) will happily lend you fishing gear and an old-school aluminum motorboat. Find a spot on Peconic Bay to reel in some bluefish or fluke. Back on dry land, head to the Farmer Bar (631-734-5410) for a hearty southern feast of smoked barbecue brisket ($10) and fried green “tomaters” ($6).
5. After dinner, pack up and catch the North Ferry to Shelter Island. Avoid André Balazs’s hipper-than-thou Sunset Beach and instead check in to one of two modish Fred Bernstein–designed cottages at the Pridwin Hotel (from $257; 631-749-0476). The next morning, book a two-hour guided kayak tour with local pundit Jay Damuck (631-749-1990) for a look at local marshes and the occasional osprey.
6. Before catching the North Ferry back to Greenport, take a slight detour to Shelter Island’s Vine Street Café (631-749-3210). Take advantage of the restaurant’s new lunch-to-go menu; with options like oven-baked country fried chicken and herb-rubbed grilled fish sandwiches, you’ll wish the ferry ride took more than seven minutes.
7. Spend the afternoon in Greenport’s Mitchell Park, where Sundays offer a wealth of vintage diversions, including an antique carousel, a lively skate park rife with local teens, and a misting field (a bunch of sprinklers).
8. On your way back to the motel, take a ride on Frank Field’s miniature locomotive (631-477-2433), just north of Mitchell Park. Rides aren’t strictly for kids—about half of Frank’s passengers are grown-ups—so don’t be ashamed to hop onboard.
9. Spend the last leg of your North Fork trip at Harbes Family Farm (631-298-0800). Dart through the labyrinthine corn mazes (pictured, right) (sadly, without a caped David Bowie), set up the kids with pony and haystack rides, and indulge everyone’s sweet tooth with Harbes’s homemade candy apples.