9 days in Vermont Itinerary

9 days in Vermont Itinerary

Created using Inspirock Vermont travel planner

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Route & dates

9 days in Vermont Itinerary

Start: Boston
Drive:  3​h
1
Bennington
— 2 nights
Drive:  1​h 45​min
2
Woodstock
— 3 nights
Drive:  1​h 30​min
3
Stowe
— 3 nights
Drive:  3​h 30​min
End: Boston

2
nights
Bennington

Bennington ©
Bennington is a town in Bennington County, Vermont, in the United States. Satisfy your inner culture vulture at Bennington Museum and New Catholic Cemetery. Your inner history buff will appreciate The Old First Church and Robert Frost Stone House Museum. Explore the numerous day-trip ideas around Bennington: Pittsfield (Herman Melville's Arrowhead & Balderdash Cellars) and National Shrine of the Divine Mercy (in Stockbridge). There's lots more to do: take in the views from Silk Road Covered Bridge, look for gifts at Bringing You Vermont, and examine the collection at The Bennington Center for the Arts.

To see more things to do, reviews, other places to visit, and tourist information, read our Bennington trip planner.

Boston to Bennington is an approximately 3.5-hour car ride. Traveling from Boston in September, plan for a bit cooler nights in Bennington, with lows around 48°F. Finish your sightseeing early on the 16th (Mon) so you can drive to Woodstock.

Things to do in Bennington

Historic Sites Museums Shopping

Side Trips

Pittsfield, National Shrine of the Divine Mercy, Robert Frost Stone House Museum
Highlights from your plan
Bennington Museum ©
Bennington Museum
National Shrine of the Divine Mercy ©
The Old First Church ©
The Old First Church

3
nights
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. Your cultural itinerary includes sights like Calvin Coolidge Homestead and Billings Farm & Museum. You'll explore the less-touristy side of things at Mount Tom and FH Gillingham & Sons General Store. Go for a jaunt from Woodstock to Salisbury to see Black Bear Vineyard about 1h 15 min away. There's much more to do: explore the activities along Ottaquechee River, snap pictures at Taftsville Covered Bridge, look for all kinds of wild species at New England Falconry, and relax in the rural setting at Sugarbush Farm.

To find photos, other places to visit, more things to do, and other tourist information, refer to the Woodstock online tour itinerary planner .

Drive from Bennington to Woodstock in 2 hours. In September, plan for daily highs up to 75°F, and evening lows to 50°F. Finish your sightseeing early on the 19th (Thu) so you can drive to Stowe.

Things to do in Woodstock

Parks Nature Historic Sites

Side Trips

Calvin Coolidge Homestead, Black Bear Vineyard
Highlights from your plan
FH Gillingham & Sons General Store ©
Mount Tom ©
Mount Tom
New England Falconry ©
New England Falconry

3
nights
Stowe

Stowe ©
Stowe bustles in winter when skiers and snowboarders flock here to challenge themselves on the long, steep trails careening down Vermont's tallest peak, Mt.
Your inner history buff will appreciate Ethan Allen Homestead and Tea at the Governor's House. Boyden Valley Winery & Spirits and Remarkable Things at Stowe Craft are good opportunities to explore the local culture. There's lots more to do: take in the dramatic scenery at Moss Glen Falls, indulge your thirst for a good beer at Stowe Cider, sample the fine beverages at Green Mountain Distillers, and snap pictures at Giles W. Dewey Memorial Bridge.

To see traveler tips, reviews, and other tourist information, read our Stowe online attractions planner .

Traveling by car from Woodstock to Stowe takes 1.5 hours. Alternatively, you can do a combination of bus and train; or take a train. In September, daytime highs in Stowe are 73°F, while nighttime lows are 48°F. Wrap up your sightseeing on the 22nd (Sun) to allow time to drive back home.

Things to do in Stowe

Breweries & Distilleries Nature Parks

Side Trips

Ethan Allen Homestead, Green Mountain Distillers, Tea at the Governor's House, Boyden Valley Winery & Spirits
Highlights from your plan
Moss Glen Falls ©
Moss Glen Falls
Boyden Valley Winery & Spirits ©
Boyden Valley Winery & Spirits
The Alchemist ©
The Alchemist

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