Winding Road Tours was founded on the guiding principle that the view from a bike, kayak, or trail is better than the view from a cubicle any day. We should know! After many years of merely existing at cubicles by day but then reveling in what the outdoors had to offer during evenings and on weekends, we decided to step off the corporate treadmill, take a deep breath, and try to experience life from a different point of view.
From this decision, Winding Road Tours was born.

With this in mind, we’ve designed our trips to take you outside of your daily routine by simply taking you outside. Join us for a day or a weekend as we take you on a scenic ride through the coastal villages of Long Island’s North Fork, or the pristine, historic streets of Shelter Island. Enjoy a gourmet catered lunch featuring locally grown foods. Spend time touring and tasting in Long Island’s burgeoning wine country.

Take all of this in while being lead by experienced, knowledgeable, and friendly guides. Whether it’s fixing a flat, answering a question about local wines, or giving you the inside scoop on where to pick the best local strawberries, we strive to provide customer service that is second to none.

Please take a look at the rest of the site to learn more about our trips and to read testimonials from guests about recent trips.

Thank You for visiting our website and we look forward to you joining us on the Winding Road.

Russ and Jim
Winding Road Tours Founders