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Orange to Brattleboro
This route was brought to you by:
RouteXpert Paul Hedges - Adv RouteXpert
Last edit: 07-01-2020
Route Summary
A great days riding along this one way route through Western Massachusetts and South Vermont. A great combination of scenery and twisty roads.
Along which you will find some of the best New England roads and some of the best New England views. The roads and scenery alone make this a 4 star ride
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Verdict
Duration
5h 19m
Mode of travel
Car or motorcycle
Distance
264.06 km
Countries
Mount Greylock Memorial WP38
RouteXpert Review
The day starts in Orange, Massachusetts as you head out of town on the 2a a quick left and you head south towards Lake Wyola (WP3)
Arriving in Shutesbury take a right and continue along towards Leverett Pond (WP6)
Head across the Connecticut River (WP8) and then turn right and ride to the top of Sugarloaf Mountain (WP9). Back on the road and it is a quick coffee break at Subway (WP10)
Continue the 116, after passing through Conway look out for one of the covered bridges New England is famous for (WP13) keep riding the winding 116 passing through Ashfield until turning right onto the 112. Trees line the curves as you head north to Shelburne Falls. Here take some time to view the famous potholes in the river (WP19). Continue north on the 112 until taking a right onto the quiet Adamsville Road. Ride the twisting back roads until you meet up again with the Mohawk Trail. This road is a continually curving road that makes it’s way through the Florida State Forest. There are plenty of opportunities to take photographs across the mountain views before stopping for lunch at the Golden Eagle (WP34) while enjoying the views across the valley. Heading down the hillside ride through North Adams before turning left and heading towards Mount Greylock. Ride up the twisting road to the highest point in Massachusetts and take time to visit the Veterans War Memorial Tower and look out across the countryside. 90 miles visibility is possible if the weather is good. $10 to park at the top but the views alone make that feel inexpensive.
Head back down the mountain, back through North Adams and take the 8 heading north. This road is made of long easy curves as it leads you through the surrounding hills. Take a left on the 100 towards Whitingham and pass the huge Harriman Reservoir. Pass through Whitingham and continue north until reaching the Molly Start Trail. Pull over at the Hogback overlook and take in the views (WP49). There is also a chance to visit the Vermont Distillery and see what is on offer. The easy flowing road continues until you reach the Vermont Maple Museum (WP50) where there is never a reason not to buy maple good maple syrup. Follow the road along until you reach the town of Brattleboro and a stop at the Flamingo Diner for a coffee to finish the days riding (WP53)

Salmon Falls WP19
view from Mount Sugarloaf WP9
Links
Mount Greylock
Vermont Distillers
Vermont Maple Museum
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Disclaimer
Use of this GPS route is at your own expense and risk. The route has been carefully composed and checked by a MyRoute-app accredited RouteXpert for use on TomTom, Garmin and MyRoute-app Navigation.

Changes may nevertheless have occurred due to changed circumstances, road diversions or seasonal closures. We therefore recommend checking each route before use.

Preferably use the route track in your navigation system. More information about the use of MyRoute-app can be found on the website under 'Community' or 'Academy'.
Nearby routes
Massachusetts
About this region
Massachusetts, officially the Commonwealth of Massachusetts, is the most populous state in the New England region of the United States. It borders on the Atlantic Ocean to the east, Connecticut to the southwest and Rhode Island to the southeast, New Hampshire to the northeast, Vermont to the northwest, and New York to the west. The capital of Massachusetts is Boston, which is also the most populous city in New England. It is home to the Greater Boston metropolitan area, a region influential upon American history, academia, and industry. Originally dependent on agriculture, fishing and trade, Massachusetts was transformed into a manufacturing center during the Industrial Revolution. During the 20th century, Massachusetts's economy shifted from manufacturing to services. Modern Massachusetts is a global leader in biotechnology, engineering, higher education, finance, and maritime trade.Massachusetts was a site of early English colonization: the Plymouth Colony was founded in 1620 by the Pilgrims of the Mayflower, and in 1630 the Massachusetts Bay Colony, taking its name from the indigenous Massachusett, established settlements in Boston and Salem. In 1692, the town of Salem and surrounding areas experienced one of America's most infamous cases of mass hysteria, the Salem witch trials. In 1777, General Henry Knox founded the Springfield Armory, which, during the Industrial Revolution, catalyzed numerous important technological advances, including interchangeable parts. In 1786, Shays' Rebellion, a populist revolt led by disaffected American Revolutionary War veterans, influenced the United States Constitutional Convention. In the 18th century, the Protestant First Great Awakening, which swept Britain and the Thirteen Colonies, originated from the pulpit of Northampton preacher Jonathan Edwards. In the late 18th century, Boston became known as the "Cradle of Liberty" for the agitation there that later led to the American Revolution.
The entire Commonwealth of Massachusetts has played a powerful scientific, commercial, and cultural role in the history of the United States. Before the American Civil War, Massachusetts was a center for the abolitionist, temperance, and transcendentalist movements. In the late 19th century, the sports of basketball and volleyball were invented in the western Massachusetts cities of Springfield and Holyoke, respectively. In 2004, Massachusetts became the first U.S. state to legally recognize same-sex marriage as a result of the Massachusetts Supreme Judicial Court's decision in Goodridge v. Department of Public Health. Many prominent American political dynasties have hailed from the state, including the Adams and Kennedy families. Harvard University in Cambridge is the oldest institution of higher learning in the United States, with the largest financial endowment of any university, and Harvard Law School has educated a contemporaneous majority of Justices of the Supreme Court of the United States. Kendall Square in Cambridge has been called "the most innovative square mile on the planet", in reference to the high concentration of entrepreneurial start-ups and quality of innovation which have emerged in the vicinity of the square since 2010. Both Harvard and MIT, also in Cambridge, are perennially ranked as either the most or among the most highly regarded academic institutions in the world. Massachusetts residents have been described by the World Population Review as having the highest average IQ of all U.S. states, exceeding 104, and the state's public-school students place among the top tier in the world in academic performance. The state has been ranked as one of the top states in the United States for citizens to live in, as well as one of the most expensive.
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