6 days in Woodstock & Southern Vermont Itinerary

6 days in Woodstock & Southern Vermont Itinerary

Created using Inspirock Vermont itinerary builder

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Route & dates

6 days in Woodstock & Southern Vermont Itinerary

Start: Newark
Drive:  5​h
1
Woodstock
— 1 night
Drive:  1​h
2
Grafton
— 1 night
Drive:  1​h
3
Dorset
— 1 night
Drive:  15​min
4
Manchester
— 2 nights
Drive:  4​h 30​min
End: Newark

1
night
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. On the 23rd (Tue), take a peaceful walk through Mount Tom, steep yourself in history at Calvin Coolidge Homestead, and then contemplate the waterfront views at Ottaquechee River. Here are some ideas for day two: steep yourself in history at FH Gillingham & Sons General Store, look for all kinds of wild species at New England Falconry, then examine the collection at American Precision Museum, and finally immerse yourself in nature at Ascutney State Park.

To see maps, ratings, more things to do, and tourist information, you can read our Woodstock holiday planner.

Newark to Woodstock is an approximately 5-hour car ride. You can also do a combination of flight and car. Traveling from Newark in July, Woodstock is slightly colder at night with lows of 59°F. Cap off your sightseeing on the 24th (Wed) early enough to go by car to Grafton.

Things to do in Woodstock

Parks Nature Historic Sites

Side Trips

Calvin Coolidge Homestead, Ascutney State Park, American Precision Museum
Highlights from your plan
Mount Tom ©
Mount Tom
Ascutney State Park ©
Ascutney State Park
New England Falconry ©
New England Falconry

1
night
Grafton

Grafton ©
Grafton is a town in Windham County, Vermont, United States. Kick off your visit on the 25th (Thu): take in the exciting artwork at Sherwin Art Glass, see the interesting displays at Mill Museum, take an in-depth tour of Grafton Historical Society, then take in the exciting artwork at Gallery North Star, and finally view the masterpieces at Jud Hartmann Gallery.

For reviews, other places to visit, and other tourist information, refer to the Grafton journey planning tool .

Traveling by car from Woodstock to Grafton takes an hour. In July in Grafton, expect temperatures between 82°F during the day and 58°F at night. Finish your sightseeing early on the 25th (Thu) to allow enough time to travel to Dorset.

Things to do in Grafton

Museums Shopping

Side Trips

Mill Museum, Sherwin Art Glass
Highlights from your plan
Grafton Historical Society ©
Grafton Historical Society
Mill Museum ©
Mill Museum
Sherwin Art Glass ©
Sherwin Art Glass

1
night
Dorset

Dorset ©
Dorset is a town in Bennington County, Vermont, United States. Start off your visit on the 26th (Fri): stop by Dorset Union Store, then relax in the rural setting at Merck Forest & Farmland Center, then get a taste of life in the country at Mountain View Ranch, and finally immerse yourself in nature at Emerald Lake State Park.

To find other places to visit, ratings, where to stay, and tourist information, use the Dorset itinerary app .

Traveling by car from Grafton to Dorset takes an hour. In July in Dorset, expect temperatures between 79°F during the day and 59°F at night. Wrap up your sightseeing on the 26th (Fri) to allow time to drive to Manchester.

Things to do in Dorset

Parks Nature Shopping

Side Trips

Merck Forest & Farmland Center, Mountain View Ranch
Highlights from your plan
Emerald Lake State Park ©
Emerald Lake State Park
Merck Forest & Farmland Center ©
Merck Forest & Farmland Center
Dorset Union Store ©
Dorset Union Store

2
nights
Manchester

Manchester ©
Manchester is a town in, and one of two shire towns (county seats) of, Bennington County, Vermont, United States. Do some cultural sightseeing at Hildene, The Lincoln Family Home and Saratoga Monument. Eschew the tourist crowds and head to Equinox Preservation Trust and North Meadow Farm. Step out of Manchester to go to Woodford and see Woodford State Park, which is approximately 32 minutes away. There's still lots to do: explore the activities along Battenkill River, immerse yourself in nature at Lake Shaftsbury State Park, take your sightseeing to a higher altitude at Bromley Mountain, and look for gifts at Northshire Bookstore.

To see photos, ratings, other places to visit, and more tourist information, read our Manchester online vacation planner .

You can drive from Grafton to Manchester in an hour. In July, plan for daily highs up to 81°F, and evening lows to 58°F. Cap off your sightseeing on the 27th (Sat) early enough to travel back home.

Things to do in Manchester

Parks Nature Historic Sites

Side Trips

Woodford State Park, Lake Shaftsbury State Park, Battenkill River, Saratoga Monument
Highlights from your plan
Hildene, The Lincoln Family Home ©
Hildene, The Lincoln Family Home
Woodford State Park ©
Woodford State Park
Lake Shaftsbury State Park ©
Lake Shaftsbury State Park