SECTION 1 EAST

This segment heads directly east from Greenfield, quickly crossing the Connecticut River while meandering through historic tobacco and sod farms. You will ride north of the Quabbin Reservoir, passing through picturesque New England towns such as New Salem, Leverett, and Petersham. In Petersham, take a moment to stop at “The Store” and relax on the town common with a quick snack. From there, prepare for some challenging roads that will test your riding abilities as you navigate back north into beautiful state forest areas. Harvard Forest, Federation State Women’s Forest, and Wendell State Forest are all part of this section, providing fantastic opportunities for adventure biking. The journey concludes with a brief stop at the top of Poets Tower before returning to your hotel, covering a total of 155 miles. 

SECTION 2 SOUTH

This day presents an opportunity to truly challenge yourself from the start; Hawk Road is a must-see. Occasionally, you may encounter a sign indicating that it is not a through road, but this is typically intended to deter cars. Ensure you are prepared for tough terrain before embarking on this journey. This section is often regarded as the most challenging of all the segments on the PPAT, and it features two of my favorite lunch spots. While both locations are a bit off the main route, the detour is certainly worthwhile. Liston’s Bar and Grill in Worthington may serve the best burger you’ve ever had, along with a wonderful outdoor seating area. The Chesterfield General Store on Route 143 in Chesterfield is another fantastic stop; if they are making wood-fired pizzas that day, you absolutely must try one! Keep an eye out for these two locations on the waypoint list and make sure to visit them! You will also pass by Glendale Falls, so take a moment to dismount and enjoy the view. Nearby, there is a charming self-service ice cream stand in Middlefield. This section promises a full day filled with incredible adventure riding, adding 156 miles to your odometer!  

SECTION 3 WEST

This day promises to be the most exhilarating on all the PPAT routes, covering 174 miles of fantastic riding! It also features many of my favorite roads in western Massachusetts. Begin your adventure early and be prepared to spend the entire day on this route; you will cherish every moment! Departing from the hotel, you will head west, slightly south of the renowned Mohawk Trail. Charming towns such as Buckland, Hawley, and Savoy will captivate you with their rural charm and delightful dirt roads. Before returning east, you will conquer the highest peak in Massachusetts, Mount Greylock! Then, navigate the famous Hairpin turn in Clarksburg, MA! From this point, you can opt for the “hard” section leading to Raycroft Lookout. Dismount and take the brief hike to the lookout. If you’re seeking a challenge afterward, continue on the hard track or return to the regular route heading north to Vermont. It’s a brief stop in the Green Mountain state, but it’s one you shouldn’t miss. Here, you’ll discover another fantastic dining spot. The Readsboro General Store may appear to be one of those places you’d simply pass by, but that would be a missed opportunity. Stop in and enjoy a meal! Believe me, you will be glad you did!  

SECTION 4 – NORTH

Today’s journey will lead you once again into the lush landscapes of the Green Mountain State. You will traverse a few miles of the renowned Puppy Dog Route, which was among the original downloadable GPS routes for Adventure Rides. This was one of the very first rides I embarked on when I acquired my first KLR back in the late 90s. Following a swift ride along the green river, you will return to MA and cross the CT river once more. This segment also briefly takes you into Southern NH, providing an opportunity to experience Falls Road. This road begins in NH but soon descends into Royalton MA. It’s important to note that this is not an easy road, so be cautious if you decide to take it! After this exhilarating ride, you will navigate through several state forest trails, leading you back to Greenfield. With another 140 miles of incredible adventure riding, you will have successfully completed the Piccadilly Pineapple Adventure Trail, Cloverleaf edition!