15 days in Vermont, Toronto & New York City Itinerary

15 days in Vermont, Toronto & New York City Itinerary

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Route & dates

15 days in Vermont, Toronto & New York City Itinerary

Start: London
Fly + Drive:  13​h 15​min
1
Bennington
— 2 nights
Drive:  1​h 45​min
2
Woodstock
— 3 nights
Drive:  1​h 45​min
3
Shelburne
— 2 nights
+2
Drive + Fly + Drive:  11​h 45​min
4
Toronto
— 1 day
+2
Drive + Fly + Drive:  9​h
5
New York City
— 5 nights
Fly:  11​h 15​min
End: London

2
nights
Bennington

Bennington ©
Bennington is a town in Bennington County, Vermont, in the United States. Start off your visit on the 8th (Tue): appreciate the history behind Bennington Battle Monument, then explore the activities along Lake Shaftsbury State Park, then take in the views from Bridge at the Green, and finally admire the majestic nature at Woodford State Park. On the next day, stroll the grounds of New Catholic Cemetery, relax in the rural setting at Earth Sky Time Community Farm, then take in nature's colorful creations at Hildene, The Lincoln Family Home, and finally relax in the rural setting at Mad Tom Orchard.

To see ratings, maps, traveler tips, and more tourist information, use the Bennington trip planner .

London, UK to Bennington is an approximately 13.5-hour combination of flight and car. The time zone difference when traveling from London to Bennington is minus 5 hours. When traveling from London in September, plan for somewhat warmer days and about the same nights in Bennington: temperatures range from 27°C by day to 10°C at night. Wrap up your sightseeing on the 9th (Wed) early enough to drive to Woodstock.

Things to do in Bennington

Parks Nature Historic Sites

Side Trips

Manchester, Lake Shaftsbury State Park, Bridge at the Green, Mad Tom Orchard, Woodford State Park
Highlights from your plan
Lake Shaftsbury State Park ©
Lake Shaftsbury State Park
New Catholic Cemetery ©
New Catholic Cemetery
Mad Tom Orchard ©
Mad Tom Orchard

3
nights
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. Change things up with these side-trips from Woodstock: Baird Farm Vermont Maple Syrup (in Chittenden), Dog Mountain Home of Stephen Huneck Gallery (in Saint Johnsbury) and Brandon (Maple View Farm Alpacas & Inn to Inn). There's lots more to do: get curious at Montshire Museum of Science, walk around Paradise Park, take in the history at Hubbardton Battlefield, and catch a live event at Giorgetti Park.

For reviews, photos, maps, and more tourist information, read Woodstock trip itinerary planning site .

You can drive from Bennington to Woodstock in 2 hours. In September in Woodstock, expect temperatures between 28°C during the day and 11°C at night. Cap off your sightseeing on the 12th (Sat) early enough to go by car to Shelburne.

Things to do in Woodstock

Parks Outdoors Historic Sites

Side Trips

Brandon, Eshqua Bog Natural Area, Montshire Museum of Science, Giorgetti Park, Baird Farm Vermont Maple Syrup
Highlights from your plan
Montshire Museum of Science ©
Montshire Museum of Science
Inn to Inn ©
Inn to Inn

2
nights
Shelburne

Shelburne is a town in southwestern Chittenden County, Vermont, in the United States. Start off your visit on the 13th (Sun): relax in the rural setting at Hacketts Orchard, then trek along Stowe Recreation Path, and then relax in the rural setting at Dakin Farm. Keep things going the next day: stroll through D.A.R. State Park and then learn the secrets of beer at a beer tour and tasting.

To find where to stay, reviews, ratings, and more tourist information, read our Shelburne road trip planning site .

Drive from Woodstock to Shelburne in 2 hours. Alternatively, you can take a bus; or take a bus. In September, daily temperatures in Shelburne can reach 28°C, while at night they dip to 13°C. Wrap up your sightseeing on the 14th (Mon) to allow time to travel to Toronto.

Things to do in Shelburne

Tours Outdoors Parks

Side Trips

Stowe, Hacketts Orchard, Dakin Farm, D.A.R. State Park
Highlights from your plan
Beer Tastings & Tours
Stowe Recreation Path ©
Stowe Recreation Path
Hacketts Orchard ©
Hacketts Orchard

1
day
Toronto

Toronto
Toronto is a city in Woodson County, Kansas, United States, along the Verdigris River. Kick off your visit on the 15th (Tue): immerse yourself in nature at Cross Timbers State Park.

To find ratings, maps, and other tourist information, read Toronto trip itinerary planning app .

The Route module can help you plan travel from Shelburne to Toronto. The time zone difference moving from Eastern Standard Time (EST) to Central Standard Time (CST) is minus 1 hour. Plan for somewhat warmer temperatures traveling from Shelburne in September, with highs in Toronto at 33°C and lows at 19°C. Wrap up your sightseeing on the 15th (Tue) to allow time to travel to New York City.

Things to do in Toronto

Nature Parks

5
nights
New York City

New York City ©
Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
New York City is known for museums, nightlife, shopping, historic sites, and parks. Your plan includes some of its best attractions: stroll around Central Park, enjoy breathtaking views from Empire State Building, appreciate the history behind Statue of Liberty National Monument, and admire the landmark architecture of Grand Central Terminal.

To find where to stay, maps, reviews, and more tourist information, you can read our New York City vacation planner.

Explore your travel options from Toronto to New York City with the Route module. The time zone difference moving from Central Standard Time to Eastern Standard Time is 1 hour. Expect a daytime high around 31°C in September, and nighttime lows around 22°C. Wrap up your sightseeing on the 21st (Mon) to allow time to travel back home.

Things to do in New York City

Museums Parks Historic Sites
Highlights from your plan
Central Park ©
Central Park
Empire State Building ©
Empire State Building
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art

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