14 days in Vermont Itinerary

14 days in Vermont Itinerary

Created using Inspirock Vermont trip maker

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Route & dates

14 days in Vermont Itinerary

Start: New York City
Drive:  4​h 15​min
1
Manchester
— 2 nights
Drive:  1​h 30​min
2
Middlebury
— 2 nights
Drive:  1​h 30​min
3
Stowe
— 5 nights
Drive:  1​h 30​min
4
Woodstock
— 4 nights
Drive:  5​h
End: New York City

2
nights
Manchester

Manchester ©
Manchester is a town in, and one of two shire towns (county seats) of, Bennington County, Vermont, United States. Step out of the city life by going to Equinox Preservation Trust and Lye Brook Falls. Your inner history buff will appreciate Hildene, The Lincoln Family Home and Weston Priory. Go for a jaunt from Manchester to Weston to see Vermont Country Store about 30 minutes away. Next up on the itinerary: tee off at The Golf Club at Equinox, shop like a local with Southern Vermont Arts Center, and take in the awesome beauty at Bromley Mountain.

For more things to do, other places to visit, where to stay, and other tourist information, read Manchester trip itinerary maker website .

New York City to Manchester is an approximately 4.5-hour car ride. You can also take a bus; or do a combination of train and bus. Prepare for a bit cooler weather when traveling from New York City in September: high temperatures in Manchester hover around 74°F and lows are around 48°F. Cap off your sightseeing on the 25th (Wed) early enough to go by car to Middlebury.

Things to do in Manchester

Parks Outdoors Nature

Side Trips

Weston, Bromley Mountain
Highlights from your plan
Hildene, The Lincoln Family Home ©
Hildene, The Lincoln Family Home
Bromley Mountain ©
Bromley Mountain
Equinox Preservation Trust ©
Equinox Preservation Trust

2
nights
Middlebury

Middlebury ©
Middlebury is the shire town (county seat) of Addison County, Vermont, United States. Start off your visit on the 26th (Thu): don't miss a visit to Pulp Mill Covered Bridge, then identify plant and animal life at Texas Falls Recreation Area, then immerse yourself in nature at D.A.R. State Park, and finally tour the pleasant surroundings at Snake Mountain Trail. Get ready for a full day of sightseeing on the 27th (Fri): don't miss a visit to Cambridge Junction Covered Bridge, do a tasting at Lincoln Peak Vineyard, then sample the tasty concoctions at Woodchuck Cider House, then sample the tasty concoctions at Foley Brothers Brewing, and finally look for gifts at Danforth Pewter.

For more things to do, traveler tips, where to stay, and other tourist information, use the Middlebury driving holiday planner.

Traveling by car from Manchester to Middlebury takes 1.5 hours. Expect a daytime high around 73°F in September, and nighttime lows around 51°F. Wrap up your sightseeing on the 27th (Fri) early enough to drive to Stowe.

Things to do in Middlebury

Wildlife Parks Outdoors

Side Trips

Addison, Foley Brothers Brewing, Cambridge Junction Covered Bridge, Texas Falls Recreation Area, Woodchuck Cider House
Highlights from your plan
Texas Falls Recreation Area ©
Texas Falls Recreation Area
Snake Mountain Trail ©
Snake Mountain Trail
Woodchuck Cider House ©
Woodchuck Cider House

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.
Visit Smugglers Notch State Park and Ethan Allen Homestead for their historical value. Get outdoors at Stowe Recreation Path and Burlington Bike Path. Change things up with these side-trips from Stowe: Boyden Valley Winery & Spirits (in Cambridge), White's Beach (in South Hero) and North Beach Park (in Burlington). There's lots more to do: indulge your thirst for a good beer at Magic Hat Brewing Company, take in the architecture and atmosphere at Blessed Sacrament Church, look for all kinds of wild species at Missisquoi National Wildlife Refuge, and grab your bike and head to Shelburne Bay Park.

To see traveler tips and other tourist information, use the Stowe trip planner .

Getting from Middlebury to Stowe by car takes about 1.5 hours. September in Stowe sees daily highs of 73°F and lows of 48°F at night. Wrap up your sightseeing on the 2nd (Wed) early enough to drive to Woodstock.

Things to do in Stowe

Parks Outdoors Breweries & Distilleries

Side Trips

Burlington, Shelburne, White's Beach, Boyden Valley Winery & Spirits, Missisquoi National Wildlife Refuge
Highlights from your plan
Stowe Recreation Path ©
Stowe Recreation Path
Burlington Bike Path ©
Burlington Bike Path
Mount Mansfield State Forest ©
Mount Mansfield State Forest

4
nights
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. Visiting Marsh - Billings - Rockefeller National Historical Park and Montshire Museum of Science will get you outdoors. Your inner history buff will appreciate Billings Farm & Museum and Calvin Coolidge Homestead. Next up on the itinerary: sample the tasty concoctions at Harpoon Brewery, look for all kinds of wild species at Vermont Institute of Natural Science (VINS) Nature Center, explore the striking landscape at Quechee Gorge, and steep yourself in history at FH Gillingham & Sons General Store.

For maps, other places to visit, photos, and tourist information, go to the Woodstock tour itinerary planner .

Drive from Stowe to Woodstock in 1.5 hours. Alternatively, you can do a combination of train and bus; or take a train. October in Woodstock sees daily highs of 62°F and lows of 40°F at night. Cap off your sightseeing on the 6th (Sun) early enough to go by car back home.

Things to do in Woodstock

Parks Historic Sites Nature

Side Trips

Quechee, Plymouth, Montshire Museum of Science, Harpoon Brewery, Long Trail Brewing Company
Highlights from your plan
Montshire Museum of Science ©
Montshire Museum of Science
Quechee Gorge ©
Quechee Gorge

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