This year’s 50-mile ride has been updated to include new roads with just as much breathtaking scenery. Almost half the course has been updated, offering a different perspective of the area locally known as the Ascutney Basin and bringing riders through a variety of picturesque and historic landscapes.

The ride starts out at the base of Mount Ascutney and heads east on Route 44 toward Windsor. Shortly, the course bears onto Back Mountain Road (Route 44A) and winds through the tall pines of Mount Ascutney State Park for several miles. When Back Mountain Road ends and riders merge onto Route 5 South, they will pass through the little village of Ascutney before turning onto Route 131 and across the Connecticut River to New Hampshire.

Shortly after entering New Hampshire, riders can fuel up at their first rest stop, then roll north along Route 12A. This road parallels the Connecticut River and offers a wide-angle view of Mount Ascutney to the west. Watch for the train tracks around mile 10.0, which cross the road at a dangerous angle and have been known to eat wheels!

New for this year, the 50-mile course returns to Vermont through the historic Cornish-Windsor covered bridge. This 150-year old bridge is the longest wooden covered bridge in the country and is a special point of interest along the route. Use caution crossing, as the span is narrow and open to two-way traffic.

Once back in Vermont, riders will pass through Windsor and head north to the second rest stop, in Hartland. From here, the course returns to the route used in previous years, traveling further north to Quechee—home of our friends at Skinny Pancake, who are hosting the third rest stop. After refueling at the stop in Quechee, the course turns west, along the crystal waters of the Ottaquechee River. Passing the scenic Taftsville covered bridge, the road briefly turns to gravel as it heads into Woodstock.

Woodstock is a local destination, home to quaint shops, gourmet eateries, and tons of historic treasures. The 50-mile course winds through the Village of Woodstock and circles the green before leaving town on Route 106 South. On the edge of town, Woodstock Elementary School is the site of the fourth rest stop.

Route 106 is characterized by a slight, steady uphill grade for several miles, followed by a two-mile descent to the final rest stop in the crossroads village of Hammondsville. Keeper’s restaurant, at the intersection of Bailey’s Mills Road, is a local favorite for casual gourmet dining. From here, it’s a flat, two-mile ride to the intersection of Route 44 East, the final leg of the course.

After a short series of narrow turns, the road opens into a wide valley, with the mountain looming large in the foreground. Riding through the village of Brownsville on your way to the finish line, take note of the Butcher & Pantry on the right, the little store and café with an always changing and always amazing chef’s menu of breakfast, lunch, and dinner.