18 days in Middlebury, Woodstock & Manchester Itinerary

18 days in Middlebury, Woodstock & Manchester Itinerary

Created using Inspirock United States trip planner
Make it your trip
1
Middlebury
— 1 day
Drive
2
Woodstock
— 2 nights
Drive
3
Manchester
— 15 nights

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Middlebury — 1 day

Middlebury is the shire town (county seat) of Addison County, Vermont, United States. Start off your visit on the 20th (Wed): experience rural life at UVM Morgan Horse Farm, do a tasting at Lincoln Peak Vineyard, and then sample the tasty concoctions at Woodchuck Cider House.

For more things to do, traveler tips, maps, and more tourist information, read Middlebury holiday planner.

The Route module can give you travel options from your home to Middlebury. In September in Middlebury, expect temperatures between 73°F during the day and 51°F at night. Finish up your sightseeing early on the 20th (Wed) so you can go by car to Woodstock.
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Breweries & Distilleries · Wineries
Side Trip

Woodstock — 2 nights

Woodstock is the shire town of Windsor County, Vermont, United States. Start off your visit on the 21st (Thu): contemplate the long history of Marsh - Billings - Rockefeller National Historical Park. On the 22nd (Fri), you'll have a packed day of sightseeing: buy something for everyone on your list at Quechee Gorge Village Vermont Antique Mall.

To find where to stay, reviews, traveler tips, and other tourist information, read our Woodstock driving holiday planning website.

You can drive from Middlebury to Woodstock in 1.5 hours. In September, daytime highs in Woodstock are 75°F, while nighttime lows are 50°F. On the 22nd (Fri), wrap the sightseeing up by early afternoon so you can drive to Manchester.
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Parks · Historic Sites · Nature · Shopping
Side Trip

Manchester — 15 nights

Manchester is the largest city in the U.S. state of New Hampshire, the eleventh largest city in New England, and as of 2016 the largest city in northern New England, an area comprising the states of Maine, New Hampshire, and Vermont. Your day by day itinerary now includes Cold Hollow Cider Mill, Elements Hot Tub Spa and King Arthur Baking Company. Explore the numerous day-trip ideas around Manchester: Amherst (Mt. Pollux & Amherst College), New England Botanic Garden at Tower Hill (in Boylston) and Museum of Russian Icons (in Clinton). There's still lots to do: explore the world behind art at Currier Museum of Art, walk around Livingston Park, admire the landmark architecture of Castle in the Clouds, and see the interesting displays at Scouting Museum and Library.

To see maps, more things to do, photos, and more tourist information, use the Manchester online attractions planner.

You can drive from Woodstock to Manchester in 1.5 hours. Another option is to take a bus. September in Manchester sees daily highs of 76°F and lows of 55°F at night.
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Parks · Outdoors · Museums · Shopping
Side Trips