While the sprawling openness of Upstate New York (like this 518-mile waterfront route) is perfect for a long haul, what might be one of the state’s most iconic coastal journeys is sitting right at our fingertips.
Stretching 94.5 miles along Long Island’s rugged South Shore, Montauk Highway isn’t just a road–it’s a rite of passage. As the weather warms and “The End” begins to beckon, this scenic byway transforms into the ultimate summer escape, trading city skyscrapers for salt-crusted dunes and historic charm.
Think of it as New York’s answer to the Pacific Coast Highway, but with more lobster rolls, 18th-century history, and that unmistakable East End energy.
Here’s how to plan the perfect trek to the edge of the world!
New York’s most iconic seaside escape
Montauk Highway (Route 27) is far from your average commuter road–it’s a curated journey through Long Island’s most iconic beach towns.
The route officially begins at the Amityville-Copiague line and cuts through the heart of Suffolk County’s most legendary hamlets–Southampton, East Hampton, Bridgehampton, and Amagansett.
Key scenic stretches include Old Montauk Highway, which hugs the coastline with sweeping ocean views and winding, wooded terrain, and the Walking Dunes, known for their unique shifting sandy landscapes.
Must-visit stops along the route
There’s a lot to take in along the way, and every stretch offers something different to discover.
Instead of treating it as one long drive, it works just as well as a string of smaller weekend trips. Here are a few can’t-miss stops to build into your route:
- Riverhead gateway stops: grab the kids to explore the Long Island Aquarium
- Hampton Bays waterfront dining: grab a cocktail at Cowfish or RUMBA right on the Shinnecock Canal
- The Wölffer “Wine Stand” Detour: In Sagaponack, the Wölffer Estate Wine Stand offers a casual, open-air tasting experience. It’s the gold standard for sunset pours and live music in the vines
- Hamptons villages and luxe beach towns: East Hampton and Amagansett deliver a mix of upscale shopping, coffee spots, and quiet beach access
- Classic roadside bites: check out cult-favorite sweet treats like Levain Bakery and Montauk Bake Shoppe or iconic roadside staples such as Lobster Roll
- Shadmoor to Camp Hero nature stretch: as Montauk approaches, the scenery turns rugged–Shadmoor State Park offers cliffside ocean views and hiking trails, while Camp Hero State Park adds windswept paths and historic military ruins
- The Grand Finale: the road ends at Montauk Point Lighthouse, the oldest lighthouse in New York offering 360-degree Atlantic Ocean views
The trail at a glance
- Best time to go: Spring and summer bring the most to do outdoors, from beaches to winery stops, while fall brings crisp air and colorful coastal foliage for quieter, scenic drives
- Location: Runs through Long Island’s South Shore, from Amityville to Montauk Point State Park
