17 days in Vermont Itinerary

17 days in Vermont Itinerary

Created using Inspirock Vermont vacation planner

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Route & dates

17 days in Vermont Itinerary

Start: Savannah
Fly:  6​h 15​min
1
Woodstock
— 4 nights
Drive:  1​h 45​min
2
Bennington
— 4 nights
Drive:  2​h 45​min
3
Stowe
— 5 nights
Drive:  1​h 30​min
4
Middlebury
— 3 nights
Drive + Fly:  7​h 45​min
End: Savannah

4
nights
Woodstock

Woodstock
Woodstock is the shire town of Windsor County, Vermont, United States. Eschew the tourist crowds and head to President Calvin Coolidge State Historic Site and Mount Tom. Your cultural itinerary includes sights like Montshire Museum of Science and Calvin Coolidge Homestead. Step out of Woodstock to go to Plymouth and see Plymouth Artisan Cheese, which is approximately 30 minutes away. There's much more to do: snap pictures at Taftsville Covered Bridge, indulge your thirst for a good beer at Long Trail Brewing Company, brush up on your knowledge of spirits at Vermont Spirits, and explore the activities along Ottaquechee River.

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

Savannah to Woodstock is an approximately 6.5-hour flight. You can also drive; or do a combination of train and bus. When traveling from Savannah in September, plan for slightly colder days and cooler nights in Woodstock: temperatures range from 75°F by day to 50°F at night. Cap off your sightseeing on the 28th (Sat) early enough to go by car to Bennington.

Things to do in Woodstock

Parks Historic Sites Nature

Side Trips

Plymouth, Quechee, Thundering Falls Trail, Long Trail Brewing Company, Cornish-Windsor Bridge
Highlights from your plan
Montshire Museum of Science ©
Montshire Museum of Science
Long Trail Brewing Company ©
Long Trail Brewing Company

4
nights
Bennington

Bennington ©
Bennington is a town in Bennington County, Vermont, in the United States. The Old First Church and Norman Rockwell Exhibition are good opportunities to explore the local culture. Give yourself a bit of retail therapy at Bennington Potters and The Art of Humor Gallery. You'll find plenty of places to visit near Bennington: Equinox Mountain (in Arlington), Manchester (Lye Brook Falls, Southern Vermont Arts Center, & more) and Creamery Covered Bridge (in Brattleboro). And it doesn't end there: stroll the grounds of New Catholic Cemetery, take in the views from Papermill Village Bridge, don't miss a visit to Silk Road Covered Bridge, and admire the majestic nature at Jamaica State Park.

For photos, more things to do, and tourist information, refer to the Bennington trip maker site .

Traveling by car from Woodstock to Bennington takes 2 hours. In September, daily temperatures in Bennington can reach 74°F, while at night they dip to 48°F. Wrap up your sightseeing on the 2nd (Wed) early enough to travel to Stowe.

Things to do in Bennington

Parks Nature Shopping

Side Trips

Manchester, Arlington, Creamery Covered Bridge, The Art of Humor Gallery, Jamaica State Park
Highlights from your plan
Equinox Mountain ©
Equinox Mountain
The Old First Church ©
The Old First Church
Equinox Preservation Trust ©
Equinox Preservation Trust

5
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.
Relax by the water at North Beach Park and White's Beach. You'll explore the less-touristy side of things at The Alchemist and St. Anne's Shrine. Change things up with these side-trips from Stowe: Museum of Everyday Life (in Glover), Boyden Valley Winery & Spirits (in Cambridge) and Fairbanks Museum and Planetarium (in Saint Johnsbury). And it doesn't end there: explore the different monuments and memorials at Hope Cemetery, steep yourself in history at Tea at the Governor's House, take in the exciting artwork at Ziemke Glass Blowing Studio, and browse the eclectic array of goods at Burlington Farmers' Market.

For where to stay and more tourist information, use the Stowe online journey planner .

Getting from Bennington to Stowe by car takes about 3 hours. In October in Stowe, expect temperatures between 60°F during the day and 39°F at night. Finish your sightseeing early on the 7th (Mon) to allow enough time to drive to Middlebury.

Things to do in Stowe

Breweries & Distilleries Historic Sites Shopping

Side Trips

Burlington, Hope Cemetery, Tea at the Governor's House, White's Beach, St. Anne's Shrine
Highlights from your plan
Boyden Valley Winery & Spirits ©
Boyden Valley Winery & Spirits
St. Anne's Shrine ©
St. Anne's Shrine
Hope Cemetery ©
Hope Cemetery

3
nights
Middlebury

Middlebury ©
Middlebury is the shire town (county seat) of Addison County, Vermont, United States. Satisfy your inner culture vulture at Shelburne Vineyard and Lake Champlain Maritime Museum. You'll explore the less-touristy side of things at Woodchuck Cider House and Halpin Covered Bridge. When in Middlebury, make a side trip to see Texas Falls Recreation Area in Hancock, approximately 34 minutes away. There's still lots to do: indulge your thirst for a good beer at Otter Creek Brewing, make a trip to Pulp Mill Covered Bridge, stop by Danforth Pewter, and relax in the rural setting at UVM Morgan Horse Farm.

To see reviews, where to stay, other places to visit, and tourist information, refer to the Middlebury trip planning website .

Traveling by car from Stowe to Middlebury takes 1.5 hours. Expect a daytime high around 61°F in October, and nighttime lows around 42°F. Finish your sightseeing early on the 10th (Thu) to allow enough time to travel back home.

Things to do in Middlebury

Breweries & Distilleries Parks Wildlife

Side Trips

Shelburne Vineyard, Texas Falls Recreation Area, Woodchuck Cider House, Lake Champlain Maritime Museum
Highlights from your plan
Lake Champlain Maritime Museum ©
Lake Champlain Maritime Museum
Woodchuck Cider House ©
Woodchuck Cider House
Shelburne Vineyard ©
Shelburne Vineyard

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