Things to Do in Cutchogue, New York

If you’re craving peaceful vineyards, breezy beaches, and small-town charm, I always suggest heading to Cutchogue, New York. I’ve wandered its farm roads, sipped wine under sunny skies, and let the coastal quiet wash over me—and I think you’ll fall in love with it too. Whether you’re after slow drives through the North Fork, farm-fresh meals, or just a quiet place to breathe, Cutchogue makes the perfect Long Island escape.

Best Time to Visit

In my experience, the best time to go is late spring through fall (May–October). I’ve visited in summer for beach days and wine tastings, but if you go in September or October—my favorite—you’ll catch harvest festivals and crisp-air vineyard strolls that feel like a dream.

How to Get There

• If you’re traveling by car: I usually take Route 25 from New York City—it’s about a 2-hour drive out to the North Fork via the Long Island Expressway (I-495), and the scenery gets better the farther east you go.
• By Train: I’ve taken the Long Island Rail Road (LIRR) to Mattituck Station before—it’s an easy ride, and from there you’re just a quick taxi or drive to Cutchogue.
• By Ferry: When I’ve come from New England, I’ve used the ferry from New London, Connecticut to Orient Point. It’s a peaceful ride and makes Cutchogue feel like a hidden getaway.

Where to Stay

• North Fork Guest House – I’ve stayed here when I needed a quiet couple’s escape. It’s cozy, elegant, and perfectly located near beaches and wineries.
• Harvest Inn – If you want vineyard views and boutique touches, this is my pick. I’ve recommended it to friends who love wine country stays—and they’ve always thanked me.
• The Shoals Suites & Slips – I love this one for a modern waterfront stay. It’s great for boaters and beach lovers alike, and the vibe is totally laid-back.

Best Things to Do in Cutchogue