Route 30 – Middlebury to Poultney


Route 30 is one of the most underrated scenic roads in Vermont –, especially in Addison and Rutland counties. Route 30 starts near the Massachusetts border in Brattleboro and extends to Middlebury. While Middlebury is always a fun destination, make time to see the tiny towns of Cornwall, Whiting, and Sudbury, all located south of the classic New England college town.


Region: Lake Champlain Valley (Addison and Rutland counties)


Getting there: From Route 7 in Middlebury, follow signs for Route 30 south.


Miles: Middlebury to Poultney is 39 miles (one way)


Places of Interest: Middlebury College, Sudbury Congregational Church and Meeting House, Half Moon State Park (open through Columbus Day Weekend), historic Castleton (on Route 4A) and the Poultney Green (on Route 140).


Routes 2 to 114 – Montpelier to Island Pond


It’s hard to go wrong when you’re driving to the Northeast Kingdom in the fall. One of my favorite fall drives is from Montpelier to the northern reaches of Vermont’s most rural region. Foliage arrives a little early in the Northeast Kingdom (the area identified as Caledonia, Essex and Orleans counties), so plan on exploring around Oct. 1 to see the brightest colors.


Region: Central and Northern Vermont (Washington/Caledonia/Essex counties)


Getting there: Take Exit 8 off Interstate 89 toward Montpelier. Head east on Route 2 to Danville to Route 5 in St. Johnsbury. Take Route 5 north to Route 114 in Lyndonville.


Miles: Montpelier to Island Pond is 69 miles (one way)


Places of Interest: The Vermont State House, Marshfield Reservoir, Joe’s Pond, St. Johnsbury Athenaeum, Burke Mountain and Island Pond.


Route 313 in West Arlington to Sandgate Road


Whenever I’m in Manchester, my childhood home, I usually end up spending time in towns along the spine of the Green Mountains – Peru, Londonderry, Weston, and Stratton. But one of the areas I’m most excited to visit again this fall is the western part of Bennington County along the Battenkill River. We used to drive this route to New York State when I was growing up, and it still looks exactly the same as it did 40 years ago.

While you’re on Route 313, head north on Sandgate Road, which takes you around the back of Equinox Mountain and offers a completely new and beautiful perspective.


Region: Southern Vermont/Bennington County


Getting there: Take Route 7A to Arlington and travel west on Route 313. Sandgate Road will be on your right as you’re heading west.


Miles: Route 313 and Sandgate Road are a total of about 14 miles (one way)


Places of interest: West Arlington Covered Bridge, the Battenkill River and the Wayside Country Store.


Route 58 through Hazen’s Notch


Not far from Jay Peak is Route 58, which climbs to the east and changes to dirt through Hazen’s Notch in Westfield. Closed in the winter to traffic, Hazen’s Notch is not only beautiful and remote, it’s also an historic route. The notch was named after Moses Hazen — commissioned by George Washington — and his American Revolutionary forces in an attempt to reach St. John.


Region: Northern Vermont (Franklin/Orleans counties)


Getting there: Take Route 118 through Montgomery to Route 58


Miles: Route 58 through Hazens Notch is 10 miles (one way)

Places of Interest: Montgomery covered bridges, Jay Peak and The Long Trail


Chelsea Mountain Road to Route 110 in Tunbridge


Chelsea Mountain Road is a meandering dirt road that takes you from East Randolph to Route 110. The mountain road is quiet and steep in places, but less rugged and not as remote as some other highland roads in Vermont.


Once you’re on Route 110, visit Tunbridge’s covered bridges – the Flint Bridge (1845), Larkin Bridge (1902), Mill Bridge (1883; replaced in 2000), Cilley Bridge (1883), and Howe Bridge (1872).


Region: Central Vermont (Orange County)


Getting there: Take Exit 4 off Interstate 89 in Randolph and follow Route 66 east to Route 14 south. Take a left on scenic Chelsea Mountain Road in East Randolph to Route 110.


Miles: Chelsea Mountain Road is 7 miles (one way)


Places of Interest: Floyd’s General Store in Randolph Center, Tunbridge covered bridges and Tunbridge Fairgrounds


Route 131 in Cavendish


Windsor County is home to some of the prettiest towns in Vermont – Woodstock, Weston, Plymouth Notch and Chester. Route 100 is also a popular route through this region. But if you’re looking for something different, try Cavendish.


Region: Southern Vermont (Windsor County)


Getting there: Take Exit 8 off Interstate 91 and travel west onto Route 131 through Weathersfield and onto Cavendish and then Ludlow.


Miles: Route 131 from Interstate 91 to Route 103 in Ludlow is 34 miles


Places of Interest: Cavendish Stone Church, Downers Covered Bridge and Okemo Mountain Resort.


Route 121 in Saxtons River to Grafton to North Windham


I have a soft spot for the tiny village of Saxtons River in the town of Rockingham. The Saxtons River Inn, a vintage 1903 inn with a distinctive square, five-story tower, is a local landmark that’s worth visiting or photographing while you’re in town.

Head west on Route 121 through Grafton – one of Vermont’s most beautiful towns – and you’ll eventually find yourself on a dirt road that leads to North Windham. This is a gorgeous Vermont drive that is not to be missed.


Region: Southern Vermont (Windham County)

Getting there: Take Exit 6 off Interstate 89 in Bellows Falls and follow signs to Route 121 in Saxtons River.


Miles: Route 121 is 27 miles from Saxtons River to North Windham (one way)


Places of Interest: Flat Iron Exchange coffee house in Bellows Falls, Saxtons River Inn, Grafton Inn, Grafton Village Cheese and Kidder Covered Bridge


Huntington Road


By the time fall arrives, I’m usually planning most of my fall trips outside of the Burlington area. But there are plenty of beautiful, rural roads to check out during the fall season. One of my favorites is Huntington Road. As you head south from Richmond, you’ll see beautiful views of Camels Hump along the way.


Region: Lake Champlain Valley (Chittenden County)


Getting there: Take Exit 11 off Interstate 89 and take Route 2 east toward Richmond. Take a right onto Bridge Street, and then another right onto Huntington Road. Huntington Road turns into Main Road a few miles south of Richmond. The road becomes Gore Road as you get closer to Route 17.


Miles: Huntington Road/Main Road/Gore Road from Richmond to just north of Route 17 is 15 miles (one way)


Places of Interest: Old Round Church, Green Mountain Audubon and Camels Hump State Park


West Shore Road in the Champlain Islands


The nice thing about the Champlain Islands is that it’s one of the last places in Vermont for the leaves to turn, so you can enjoy fall colors well into late October. West Shore Drive in South Hero and Grand Isle hugs the shoreline of Lake Champlain and offers beautiful views of both the Adirondacks and Green Mountains.


Region: Northwest Vermont (Grand Isle County)


Getting there: Take Exit 17 off Interstate 89 and travel on Route 2 west toward the

Champlain Islands. Turn left on South Street followed by a right on West Shore Drive.


Miles: West Shore Drive is 9 miles (one way)


Places of Interest: Snow Farm Winery, Hero’s Welcome General Store and St. Anne’s Shrine