Riding Vermont’s Route 100 From Massachusetts to Memphremagog

Vermont Route 100 motorcycle ride
Vermont is still a state full of small farms. Photos by the author.

Vermont is a four-season state. It offers great skiing in the winter, sweet maple syrup in the spring and fantastic foliage in the autumn. Summer? Summer is for motorcycle riding. Vermont’s topography lends itself to incredible motorcycle roads, and State Route 100 is one of the best. Extending from Massachusetts to nearly the Canadian border, Route 100 traces the eastern flank of the Green Mountains, and it is as fine a motorcycle road as you will find anywhere.

I entered Vermont from North Adams, Massachusetts, where Route 100 zigzags through the quiet towns of Readsboro and Whitingham and loops around Harriman Reservoir before finally turning north. The first town of any size that I encountered was Wilmington, where I stopped at Dot’s Restaurant.

Vermont Route 100 motorcycle ride
A map of the route taken, by Bill Tipton/compartmaps.com.

Dot’s is a Wilmington icon. The building dates from 1832 and has been a diner since the 1930s. When Hurricane Irene hit Vermont a few years ago, the Deerfield River backed up and pushed Dot’s off its foundation. After three years and a complete foundation replacement, Dot’s has reopened, and the restaurant is every bit as popular as before.

In the morning, after a good night’s sleep and a great breakfast at the Gray Ghost Inn, I hit the road. Just north of the Gray Ghost, Route 100 twists and turns down to the river. The same storm that nearly destroyed Dot’s also wiped out this section of Route 100. By rebuilding it all at once, many of the off-camber and reducing-radius corners were fixed, yet the nature of the road was not compromised. The miles of new pavement made this section of the road a joy to ride.

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Vermont Route 100 motorcycle ride
The Gray Ghost Inn is a family-owned B&B that caters to motorcyclists and offers up a delicious traditional Vermont breakfast.

North of Weston, Route 100 tucks in tight against a series of small lakes. With a few houses on the left and swimmers and boaters on the right, I felt like I was in the scene. The heat of the sun through the pine trees and the mouthwatering smell of burgers on a grill made this stretch a feast for all five senses.

In Plymouth, I took a side trip on Route 100A to Plymouth Notch. This is where President Calvin Coolidge was born and where he retired after his presidency. Elected as Vice President in 1920, he happened to be staying here when President Harding died. His father, a notary public, swore him in as our 30th president at 2:47 a.m. in the front parlor of their home by the light of a kerosene lantern.

Vermont Route 100 motorcycle ride
Founded by Calvin Coolidge’s father, Plymouth Cheese makes some outstanding cheeses.

There are about 20 ski resorts in Vermont and more than half are near Route 100. I turned up Mountain Road toward Killington, the largest ski resort in Vermont. This multilane road with turning lanes, hotels and restaurants was a big departure from the rural landscape of the past 100 miles. It’s all designed for the winter ski crowds, but traffic was light today so I whizzed up past the golf course and the Killington Grand Hotel to the ski area parking lot. I hopped in the gondola to the summit and then hiked another couple hundred yards to the highest point. At 4,229 feet above sea level, the view from Vermont’s second-highest peak is outstanding, and I could see the Green Mountains rippling out in all directions.

Vermont Route 100 motorcycle ride
Swimmers enjoy the cool water of the Mad River.

North of Killington, Route 100 traces through the ripples. It is a fantastic motorcycle road as it dips and swoops through the woods and around the hills through Pittsfield, Stockbridge and Rochester, where I stopped for a maple milk shake at the Rochester Café.

This section of Vermont is known for the Gaps, the roads crossing the Green Mountains other parts of the country refer to as passes. In Rochester, State Route 73 heads over Brandon Gap, while to the east, Bethel Mountain Road crosses Rochester Gap. In Hancock, State Route 125 heads west over Middlebury Gap, while the dirt road to the east crosses Roxbury Gap. The partially unpaved Lincoln Gap heads out of Warren, and State Route 17, Appalachian Gap, leaves out of Waitsfield. I could spend an entire day happily zipping back and forth on these roads.

Vermont Route 100 motorcycle ride
Lower Podunk Road is two miles farther down Route 100.

Riding into Waterbury I came across the first traffic lights I had seen since Wilmington, 130 miles ago. The congestion was worth it though, as just past the final light was the Ben and Jerry’s ice cream factory. Here I toured the factory, which ended with a scoop of Ben and Jerry’s famous ice cream. Out in back is a “flavor graveyard,” a mock cemetery with granite headstones for discontinued flavors, or the “dearly depinted,” as they call them. RIP, Cool Britannia and Urban Jumble.

Vermont Route 100 motorcycle ride
Hard to find and just plain weird stuff from yesteryear is for sale at the Vermont Country Store.

Stowe, the next town on Route 100, is in a beautiful location below the 4,200-foot summit of Mount Mansfield. Despite being a big tourist town, it does not have a chain hotel, and the accommodations run the full range of amenities and prices. North of Stowe, the landscape opened up to rolling hills and farms. The fields were larger and the forest farther away. The road was full of sweeping turns with a rhythm and flow that made me crack the throttle a little bit more and smile inside my helmet, enjoying a thoroughly wonderful romp through the open country and empty highway. Farther on, I stopped at the Troy General Store. This is what a general store should be; the wooden floor creaked as I walked and stuff was hanging from the ceiling. A sandwich was being made in the deli, and I could smell a pizza in the oven.

Near Coventry, at the intersection with State Route 105, Route 100 just ends. After 200 miles, I expected something more than a 100 END sign, but, disappointingly, there it was. It was only 10 miles to the Canadian border so I decided to head there. I rode through Newport and along the east side of Lake Memphremagog to the village of Derby Line.

Vermont Route 100 motorcycle ride
St. Mary Star of the Sea church rises above Newport and Lake Memphremagog.
Vermont Route 100 motorcycle ride
The beautiful church building dominates the skyline over the lake.

The “Line,” in this case, is the border between Vermont and Canada. It passes right through the Haskell Free Library and Opera House: half of the building is in Derby Line, the other half is in Stanstead, Québec. In the reading room, the border is painted on the floor. Upon request, the librarian took my picture, where I stood with one foot in the USA and one foot in Canada. I couldn’t go any farther north without a passport.

Vermont Route 100 motorcycle ride
The Haskell Free Library and Opera House straddles the U.S./Canada border.

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