16 days in Vermont Itinerary

16 days in Vermont Itinerary

Created using Inspirock Vermont route planner

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Route & dates

16 days in Vermont Itinerary

Start: New York City
Drive:  3​h 30​min
1
Bennington
— 3 nights
Drive:  1​h 45​min
2
Woodstock
— 5 nights
Drive:  1​h 30​min
3
Saint Johnsbury
— 3 nights
Drive:  1​h 45​min
4
Shelburne
— 4 nights
Fly:  5​h
End: New York City

3
nights
Bennington

Bennington ©
Bennington is a town in Bennington County, Vermont, in the United States. Explore the numerous day-trip ideas around Bennington: Equinox Mountain (in Arlington), Vermont Country Store (in Weston) and Manchester (Equinox Preservation Trust, Hildene, The Lincoln Family Home, & more). There's much more to do: take some stellar pictures from Bennington Battle Monument, immerse yourself in nature at Woodford State Park, explore the different monuments and memorials at New Catholic Cemetery, and contemplate in the serene atmosphere at The Old First Church.

For photos, ratings, traveler tips, and other tourist information, read Bennington travel planner .

New York City to Bennington is an approximately 3.5-hour car ride. Traveling from New York City in September, expect Bennington to be a bit cooler, temps between 74°F and 48°F. Wrap up your sightseeing on the 28th (Sat) to allow time to drive to Woodstock.

Things to do in Bennington

Parks Nature Museums

Side Trips

Manchester, Arlington, Woodford State Park, Vermont Country Store
Highlights from your plan
Hildene, The Lincoln Family Home ©
Hildene, The Lincoln Family Home
Bennington Battle Monument ©
Bennington Battle Monument
New Catholic Cemetery ©
New Catholic Cemetery

5
nights
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. You'll find plenty of places to visit near Woodstock: Okemo Mountain Resort (in Ludlow) and Killington Resort (in Killington). Next up on the itinerary: experience rural life at Sugarbush Farm, take in the views from Taftsville Covered Bridge, look for all kinds of wild species at Vermont Institute of Natural Science (VINS) Nature Center, and explore the striking landscape of Marsh - Billings - Rockefeller National Historical Park.

For more things to do, other places to visit, where to stay, and other tourist information, refer to the Woodstock vacation app .

Traveling by car from Bennington to Woodstock takes 2 hours. Expect a daytime high around 75°F in September, and nighttime lows around 50°F. Wrap up your sightseeing on the 3rd (Thu) to allow time to drive to Saint Johnsbury.

Things to do in Woodstock

Parks Historic Sites Nature

Side Trips

Plymouth, Windsor, Quechee, Montshire Museum of Science, Okemo Mountain Resort
Highlights from your plan
Sugarbush Farm ©
Sugarbush Farm
Billings Farm & Museum ©
Billings Farm & Museum

3
nights
Saint Johnsbury

Saint Johnsbury ©
St. You'll find plenty of places to visit near Saint Johnsbury: Barre (Rock of Ages Granite Quarry & Hope Cemetery), Montpelier (Morse Farm Maple Sugarworks & Bragg Farm Sugar House & Gift Shop) and Fisher Railroad Bridge (in Wolcott). Next up on the itinerary: stroll around Dog Mountain Home of Stephen Huneck Gallery, admire the landmark architecture of The Dog Chapel, contemplate the waterfront views at Lake Memphremagog, and engage your brain at Museum of Everyday Life.

To find ratings, photos, other places to visit, and tourist information, refer to the Saint Johnsbury online trip itinerary builder .

Getting from Woodstock to Saint Johnsbury by car takes about 1.5 hours. In October in Saint Johnsbury, expect temperatures between 60°F during the day and 40°F at night. Finish your sightseeing early on the 6th (Sun) to allow enough time to drive to Shelburne.

Things to do in Saint Johnsbury

Parks Nature Historic Sites

Side Trips

Barre, Montpelier, Lake Memphremagog, Museum of Everyday Life, Fisher Railroad Bridge
Highlights from your plan
Morse Farm Maple Sugarworks ©
Morse Farm Maple Sugarworks
Bragg Farm Sugar House & Gift Shop ©

4
nights
Shelburne

Shelburne ©
Shelburne is a town in southwestern Chittenden County, Vermont, in the United States. Explore the numerous day-trip ideas around Shelburne: Beer Tastings & Tours (in Burlington), Stowe (Stowe Recreation Path, Moss Glen Falls, & more) and Vermont State House (in Montpelier). The adventure continues: see the interesting displays at Shelburne Museum, shop like a local with Church Street Marketplace, take in the spiritual surroundings of Round Church, and make a trip to World's Tallest Filing Cabinet.

To find more things to do, traveler tips, reviews, and more tourist information, refer to the Shelburne online trip maker .

You can drive from Saint Johnsbury to Shelburne in 2 hours. In October, plan for daily highs up to 62°F, and evening lows to 44°F. Wrap up your sightseeing on the 10th (Thu) to allow time to travel back home.

Things to do in Shelburne

Parks Trails Outdoors

Side Trips

Burlington, Stowe, Vermont State House, Round Church, Magic Hat Brewing Company
Highlights from your plan
Shelburne Museum ©
Shelburne Museum
Shelburne Farms ©
Shelburne Farms
Stowe Recreation Path ©
Stowe Recreation Path

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