This was my first trip through the Hamptons and I was honestly shocked by how beautiful the area was. It also has some of the most diverse roads I’ve found yet. You’ve got plenty of twists, crazy fast straights, an ocean-side road (with its own twists), and plenty of shit to see.

The Route

From what I understand, not even the locals went to The Big Duck. And according to my wife, the locals “don’t know what’s cool” so I guess we’ll start there.

As I didn’t know my way around the island, a buddy of mine (coincidentally has the same bike as I do, just in the wrong color) guided me through the island for 2 days. Thanks, Rodger! We spent two days touring the island and this route is our first day.

We didn’t actually start at The Big Duck but that’s where this route starts you off. Just go see it, go inside, and learn the history.

After the duck, you’ll head to route 27 on the way to some of the most beautiful twists you’ve seen. They’re truly special and you’ll see very little traffic on the way. Unless you’re going in peak summer season; then all bets are off.

After the twists through Sag Harbor, you’ll connect back on 27 which is a fast straight through Amagansett on the way to Montauk. Most of the way is a passing road to feel free to get ahead. The latter part of 27 has some fast twists but be careful here. One way in, one way out. IYKYK.

Make your way through Montauk and pay to park at the lighthouse. Stretch your legs and walk up to take in the views. Quite beautiful up there.

Grab brunch at Jon’s Pancake House in town. It’s a local legend and has been there forever. The corn beef hash and potatoes were fantastic. Can’t go wrong.

After Montauk, you can either take 27 all the way to Dune Road or take backroads to stay closer to shore and enjoy the real estate. There are some beautiful homes and roads off the main route and you can avoid some of the traffic on 27 in peak season. Up to you.

Cross Ponquogue Bridge to connect you to Dune Road and enjoy. It’s a truly special road and I took any excuse to ride it. It’s right along the water so do be careful during high tide and after rains. The puddles are going to be deeper than they seem but you should be OK. Just use your head.

👉️ Google Maps & .GPX Download Links 🔗 

Click on the Google Maps links below for a full waypoint by waypoint route. Open it in Google Maps on your phone to follow the whole route turn-by-turn.

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