8 days in Vermont Itinerary

8 days in Vermont Itinerary

Created using Inspirock Vermont tour planner

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Route & dates

8 days in Vermont Itinerary

Start: Boston
Drive:  3 h
1
Bennington
— 1 night
Drive:  2 h
2
Woodstock
— 1 night
Drive:  2 h
3
Burlington
— 2 nights
Drive:  45 min
4
Stowe
— 2 nights
Drive:  1 h 15 min
5
Saint Johnsbury
— 1 night
Drive:  3 h 45 min
End: Boston

1
night
Bennington

Bennington ©
Bennington is a town in Bennington County, Vermont, in the United States. On the 8th (Mon), look for gifts at Fiddlehead at Four Corners, explore the different monuments and memorials at The Old First Church, then explore the different monuments and memorials at New Catholic Cemetery, and finally snap pictures at Silk Road Covered Bridge. On the 9th (Tue), you'll have a packed day of sightseeing: take in the dramatic scenery at Lye Brook Falls, look for all kinds of wild species at Equinox Preservation Trust, and then look for gifts at Sugar Shack.

To see maps, ratings, and more tourist information, go to the Bennington route planner.

Boston to Bennington is an approximately 3-hour car ride. Plan for a bit cooler nights when traveling from Boston in October since evenings lows in Bennington dip to 41°F. Finish up your sightseeing early on the 9th (Tue) so you can travel to Woodstock.

Things to do in Bennington

Parks Historic Sites Wildlife

Side Trips

Manchester, Sugar Shack
Highlights from your plan
New Catholic Cemetery ©
New Catholic Cemetery
Equinox Preservation Trust ©
Equinox Preservation Trust
The Old First Church ©
The Old First Church

1
night
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. Kick off your visit on the 10th (Wed): take in the awesome beauty at Mount Tom, sample the tasty concoctions at Long Trail Brewing Company, and then contemplate the long history of Calvin Coolidge Homestead.

To see photos, traveler tips, reviews, and more tourist information, refer to the Woodstock tour itinerary planning website .

Traveling by car from Bennington to Woodstock takes 2 hours. In October in Woodstock, expect temperatures between 62°F during the day and 40°F at night. Finish your sightseeing early on the 10th (Wed) so you can drive to Stowe.

Things to do in Woodstock

Nature Parks Breweries & Distilleries

Side Trips

Long Trail Brewing Company, Calvin Coolidge Homestead
Highlights from your plan
Mount Tom ©
Mount Tom
Long Trail Brewing Company ©
Long Trail Brewing Company

2
nights
Burlington

Burlington ©
Burlington is the most populous city in the U.S. Start off your visit on the 11th (Thu): steep yourself in history at Crown Point State Historic Site, indulge your thirst for a good beer at Woodchuck Cider House, and then relax in the rural setting at Vermont Farm Tours. On the 12th (Fri), you'll have a packed day of sightseeing: contemplate in the serene atmosphere at Round Church, explore the galleries of Saint Albans Museum, and then contemplate in the serene atmosphere at St. Anne's Shrine.

To see reviews, ratings, photos, and more tourist information, go to the Burlington tour itinerary builder website .

You can drive from Woodstock to Burlington in 2 hours. Other options are to take a bus; or take a train. In October in Burlington, expect temperatures between 62°F during the day and 44°F at night. Finish up your sightseeing early on the 12th (Fri) so you can go by car to Stowe.

Things to do in Burlington

Historic Sites Museums Breweries & Distilleries

Side Trips

Round Church, Crown Point State Historic Site, Woodchuck Cider House, Saint Albans Museum, St. Anne's Shrine
Highlights from your plan
Crown Point State Historic Site ©
Crown Point State Historic Site
St. Anne's Shrine ©
St. Anne's Shrine
Woodchuck Cider House ©
Woodchuck Cider House

2
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.
Kick off your visit on the 13th (Sat): steep yourself in history at Tea at the Governor's House, then brush up on your knowledge of spirits at Green Mountain Distillers, then sample the fine beverages at Smugglers' Notch Distillery, and finally take a peaceful walk through Wiessner Woods. Get ready for a full day of sightseeing on the 14th (Sun): look for gifts at Shaw's General Store, then appreciate the views at Mad River Glen, and then do a tasting at Fresh Tracks Farm Vineyard and Winery.

For reviews, photos, traveler tips, and tourist information, read our Stowe online vacation planner .

Traveling by car from Burlington to Stowe takes an hour. Alternatively, you can take a bus. Traveling from Burlington in October, plan for a bit cooler nights in Stowe, with lows around 39°F. Finish your sightseeing early on the 14th (Sun) so you can travel to Saint Johnsbury.

Things to do in Stowe

Nature Parks Winter Sports

Side Trips

Tea at the Governor's House, Fresh Tracks Farm Vineyard & Winery, Smugglers' Notch Distillery - Maple Products - Gift Shop - Local Products, Mad River Glen, Green Mountain Distillers
Highlights from your plan
Mad River Glen ©
Mad River Glen
Fresh Tracks Farm Vineyard & Winery ©
Green Mountain Distillers ©
Green Mountain Distillers

1
night
Saint Johnsbury

Saint Johnsbury ©
St. Start off your visit on the 15th (Mon): trek along Lamoille Valley Rail Trail, then stroll through Dog Mountain, and then indulge your taste buds at Mike's Tiki Bar.

Plan trip to Saint Johnsbury with our itinerary maker to find out where to go and what to do.

Traveling by car from Stowe to Saint Johnsbury takes 1.5 hours. October in Saint Johnsbury sees daily highs of 60°F and lows of 40°F at night. Finish up your sightseeing early on the 15th (Mon) so you can travel back home.

Things to do in Saint Johnsbury

Parks Nightlife Trails

Side Trip

Mike's Tiki Bar
Highlights from your plan
Mike's Tiki Bar ©
Mike's Tiki Bar

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