The Piccadilly Pineapple Adventure Trail is a captivating network of roads that wind through some of New England’s most breathtaking landscapes.

This self-guided journey offers “adventure” routes that can be downloaded as GPX tracks for easy navigation. It features a mix of paved backcountry roads and gentle gravel paths, with the opportunity to tackle select “hero” or “expert” sections that challenge your riding skills. Currently, there are three distinct Adventure routes available, each leading you along incredible back roads, to the summits of New England’s picturesque mountains, and even to an island off the coast of Rhode Island.

All routes are situated on legal state roads, requiring a plated vehicle for completion. Those with Jeeps or other 4×4 vehicles are encouraged to explore this network as well. It’s important to remember that while this route includes dirt paths, it also has paved segments, with many of the paved roads being charming back roads that showcase the scenic beauty of Central and Western Massachusetts. Each route spans approximately 500 miles.

Please be mindful that many of these roads pass through rural areas that typically experience low traffic. Show respect to the local community and adhere to all posted speed limits. Avoid driving around closed gates, especially during early spring, a time we New Englanders refer to as “mud season.”

While most dirt roads are suitable for larger motorcycles, riders should have some prior experience with navigating such terrains. Weather can impact the condition of some of the less-maintained roads in these off-the-beaten-path areas. Certain sections may be closed in winter, making familiarity with GPS navigation crucial when facing such closures. All routes are divided into sections or days, with each day represented by a unique GPS track.

Additional tracks for more challenging roads are available for some days; however, riders have the option to simply download the daily tracks and skip the more difficult segments if they choose. In Garmin MAPSource or Basecamp, the challenging sections are highlighted in red, while the standard routes are marked in green.

The gpx file contains a collection of waypoints for fuel stations, dining options, and numerous recommendations for hotels and campgrounds. Additionally, you will find various stops that offer breathtaking views, natural wonders such as waterfalls, and other intriguing points of interest worth exploring.

Take the time to explore each of the offered routes, and when you’re ready, download the GPX file to embark on your adventure and relish the journey.