Montauk and Shelter Island Overnight Bike Tour

Your guide will show you all the best spots to explore on your bike. They will also show you the way to beaches for swimming, either during your ride, or near the campsite where you can also enjoy prepared meals around a campfire.

This bike tour has flexible mileages for each day, ranging between 18 and 60 miles per day. Take the train from Manhattan to Southampton (with your bike) and our team will meet you there to get you going. Choose from a variety of self-guided routes to ride on, all ending at a full service campground (campground has showers, flush toilets and modern amenities) near the beach where a cookout dinner awaits you.

The next day, we start your off with a hearty breakfast before we ride on to beautiful Shelter Island and then the North Fork with it's wineries and beaches. Again, you'll have route choices ranging between 18 and 60 miles, but regardless of the ride you choose, we all end the ride in downtown Greenport, with its fun, vibrant Main Street loaded with shops and attractions. The train back to Penn Station leaves at 6:11pm, arriving around 9:00pm. We will give you a dinner that you can eat on the train on your way home.