Getting Around Long Island Without Losing Your Mind

Long Island is bigger than people give it credit for, and the tourist maps always send you to the exact same three spots. If you just want the boardwalk and a saltwater taffy, fine. But if you actually want to know where people who aren't visiting from New Jersey on a weekend drive end up, here's the rundown.

Places To Go To In Long Island

The North Shore is where most guides send you. Old Westbury Gardens, Hofstra University's arboretum, the Cradle of Aviation Museum. They're all legit. The problem is that these places sit within a five-mile radius of each other, meaning traffic on Route 108 and Northern Boulevard turns a simple trip into a 90-minute ordeal on any Saturday from Memorial Day through Labor Day. I learned this the hard way in July 2019 when I tried to hit three museums in one afternoon. My workaround was to hit the South Shore instead on those same days and just go north on weekdays. The museums were half-empty, the parking was free, and I actually had time to read the plaques instead of racing back to the car. Down the South Shore, Fire Island gets all the attention, and it deserves some of it. Cherry Grove and Robert Moses are the usual spots. The ferry from Patchogue runs about every hour in summer and costs roughly $8 each way for pedestrians. You can bring a cooler on but there's a weight limit and the bags get checked at the dock. Don't try to sneak a full six-pack through security—the checkpoint guys have seen every trick and they don't care about your excuses. Bring cash for the shower houses. Card-only signs outside don't mean the inside takes cards. The East End is a different beast entirely. The vineyards along the North Fork draw a crowd that peaks around 3pm on weekends. I've found that going at noon on a Thursday and hitting two or three tastings before the buses arrive gives you a much better experience. Some wineries like Bedell and Wölffer will let you reserve a parking spot ahead of time during harvest season, which saves you from circling for 40 minutes. The South Fork, around Montauk, is where you go if you want ocean views and lobster rolls that cost $32 and somehow taste worth it. Lighthouse Beach has a $10 car fee in season. There's no shade. Bring water.

For something most visitors miss, check out the Long Island Agricultural Preserve near Riverhead. It's not flashy. There's no admission fee. But the pumpkin patches in October and the apple orchards in September are legitimately some of the best produce you'll find anywhere in the state, and the farm stands along Route 25 between Riverhead and Southold sell things you can't get at a regular grocery store. Peaches in August. Heirloom tomatoes in July. If you time it right, you can fill your trunk for under $40. One thing nobody tells you about Long Island travel is that the LIRR changes schedules significantly on weekends. The Friday evening runbacks after Yankees games at Citi Field can push departure times back by 20 or 30 minutes depending on the line. If you're relying on the train to get to Jones Beach or Ronkonkoma on a game day, add an extra hour to your trip time or just drive. The parking at Jones Beach has a $12 fee on summer weekends and the lots near the main bathhouse fill by 10am. I learned to park at the Dune Road lot instead and walk about ten minutes to the beach. Same sand, half the wait. Gardiner's Bay on the far East End is another spot that shows up on nobody's list. It's a shallow inlet between the North and South Forks with a public boat launch at Shinnecock Neck. The water is calm enough for kayaking even if you've never paddled before, and there's a small parking area off Route 112 that holds maybe six cars. Bring bug spray. The no-see-ums in late June will eat you alive if you're not prepared.