Travel one of the ten best roads to drive in the U.S., and enjoy bucolic rural scenery, hiking, art, ice cream factory, rafting, and an 1800s village store, church, and inn.

Readsboro Falls, VT route mapBillboards are not permitted along roadways in Vermont and, in some places, paving of certain roads is prohibited to safeguar the state’s bucolic, rural environment. As a result, many of the major routes that traverse Vermont are exceptionally picturesque. Ranked by many as one of the 10 best roads in America to drive, Route 100 extends from the southern edge of Vermont to its northern border. And the question, “what’s not to like?” On this tour, you can take your pick–do some hiking, eat ice cream,  look at art,  or just enjoy the scenery. This drive will take you north on Route 100 starting just north of Stamford, a small city nestled between the Taconic and  Hoosac  mountain ranges. For the first few miles, the Hoosic River flows parallel to the road. After Readsboro Falls, the road follows the Deerfield River with its stunning waterfalls. Continue past Readsboro to Whitingham,
the hometown of Brigham Young, the well known Mormon leader and founder of Salt Lake City. In the town of Wilmington, you’ll find plenty of  antique stores and shops including Left Bank Antiques in an 1850s bank building. You can also stop in at the Mount Snow Valley Chamber of Commerce for brochures on the area’s attractions and events.

Continue north to West Dover, a town with a Historic District–including a church, a village store,  and inn–dating from the early- to mid-1800s. The Stratton ski area is also just around the corner. West Wardsboro is one more town steeped in New England history. Chartered in 1786, the town was home to Samuel Hammond, who took part in the raid popularly known as the Boston Tea Party. Public whippings for minor offenses were carried out here until the early-1800s while crimes like blasphemy carried a death penalty.  Visit the Jamaica State Park for a white water rafting adventure on the West River. Nearby, South Londonderry has many beautiful homes dating from the late-1800s when the rich and the famous mill owners settled in the area. Next, you’ll see Weston, another picturesque town centered on a village green. During the summer, you may be able to watch  a performance at the Weston Playhouse; or, any time of year, visit the Weston Priory, a small Benedictine monastery. The Whales in Vermont Gallery, in one of the Grist Mill yard’s original edifices, has some wonderful wildlife and environmental art. The Coolidge State Forest and the Calvin Coolidge Homestead  are in the nearby hamlet of Plymouth.

You can load up on local Vermont products at the Granville Manufacturing Company, just north in Granville. Take a tour to find how some of the woodcrafts are made. Just north of Granville, park your vehicle at Moss Glen Falls to watch one of the prettiest waterfalls in Vermont. Just before Waterbury Center is the Ben & Jerry’s Factory, where you can tour the popular ice cream plant and see how your favorite flavors are made. The Stowe Hollow covered bridge (constructed in 1844) leads to the “Ski Capital of the World”–but there’s plenty of activities to do in this scenic resort town at any time of year. The drive finishes in the city of Newport. Look for the Goodrich Memorial Library, constructed in 1898 and featuring historic paintings, household utensils, photographs, and stuffed animals.

Starting Point:
Readsboro Falls, VT

Distance of Drive:
200 miles

Must Eat:
The Old Mill Inn
18 North Main St., Wilmington, VT 05363
Phone: 802-464-3700
Call ahead to confirm hours of operation.

Check out the waffle weaves! The world's best car drying towel.

Best Time of Year for Drive:
Spring to Fall

Points of Interest on Drive:
Moss Glen Falls
Ben & Jerry Factory
Jamaica State Park

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Filed under: Best Road Trips