60 days in Vermont Itinerary

60 days in Vermont Itinerary

Created using Inspirock Vermont route planner

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Route & dates

60 days in Vermont Itinerary

Start: New York City
Drive:  6​h 30​min
1
Derby
— 11 nights
Drive:  1​h 30​min
2
Stowe
— 12 nights
Drive:  1​h 30​min
3
Middlebury
— 12 nights
Drive:  1​h 30​min
4
Woodstock
— 13 nights
Drive:  1​h 45​min
5
Manchester
— 11 nights
Drive:  4​h 15​min
End: New York City

11
nights
Derby

Derby ©
Museum-lovers will appreciate Old Stone House Museum and Bread and Puppet Theater. Get outdoors at Jay Peak Ski Resort and Maidstone State Park. Venture out of the city with trips to Museum of Everyday Life (in Glover), Hazen's Notch (in Montgomery) and Hill Farmstead Brewery (in Greensboro Bend). On the 28th (Sun), spend an exhilarating day on the slopes at Burke Mountain Resort.

To see photos, other places to visit, reviews, and tourist information, refer to the Derby route builder tool .

New York City to Derby is an approximately 6-hour car ride. You can also fly. In April, Derby is slightly colder than New York City - with highs of 48°F and lows of 29°F. On the 3rd (Fri), you're off toStowe.

Things to do in Derby

Parks Outdoors Nature

Side Trips

East Burke, Jay, Newport, Glover, Brighton State Park
Highlights from your plan
Jay Peak Resort ©
Jay Peak Resort
Bread and Puppet Theater ©
Bread and Puppet Theater
Old Stone House Museum ©
Old Stone House Museum

12
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.
Shelburne Farms and Tea at the Governor's House will appeal to history buffs. Step out of the city life by going to Stowe Recreation Path and Burlington Bike Path. You'll find plenty of places to visit near Stowe: Beverage Warehouse (in Winooski), Burlington (North Beach Park, Vintage Photography Emporium, & more) and Goodsell Ridge Preserve (in Isle La Motte). There's lots more to do: admire the majestic nature at Alburg Dunes State Park, kick back and relax at White's Beach, take your sightseeing to a higher altitude at Mount Mansfield State Forest, and do a tasting at Snow Farm Vineyard and Winery.

To see traveler tips, where to stay, and tourist information, refer to the Stowe trip itinerary maker website .

Getting from Derby to Stowe by car takes about 1.5 hours. May in Stowe sees daily highs of 68°F and lows of 43°F at night. Finish up your sightseeing early on the 15th (Wed) so you can go by car to Middlebury.

Things to do in Stowe

Parks Outdoors Winter Sports

Side Trips

Burlington, Shelburne, South Hero, Jeffersonville, Morrisville
Highlights from your plan
Stowe Recreation Path ©
Stowe Recreation Path
Shelburne Museum ©
Shelburne Museum
Burlington Bike Path ©
Burlington Bike Path

12
nights
Middlebury

Middlebury ©
Middlebury is the shire town (county seat) of Addison County, Vermont, United States. Step out of the city life by going to Snake Mountain Trail and Middlebury College Snow Bowl. Let the collections at Mahaney Center for the Arts and New England Maple Museum capture your imagination. You'll find plenty of places to visit near Middlebury: Waitsfield (Mad River Glen & Mad River), Warren (Warren Falls, Sugarbush Resort, & more) and Brandon (Foley Brothers Brewing, Neshobe River Winery, & more). There's lots more to do: sample the tasty concoctions at Woodchuck Cider House, stop by Danforth Pewter, glide through natural beauty at Rikert Nordic Center, and examine the collection at Vermont Marble Museum.

For other places to visit, traveler tips, where to stay, and more tourist information, read our Middlebury travel route website .

You can drive from Stowe to Middlebury in 1.5 hours. In May in Middlebury, expect temperatures between 69°F during the day and 47°F at night. Finish up your sightseeing early on the 27th (Mon) so you can go by car to Woodstock.

Things to do in Middlebury

Parks Outdoors Winter Sports

Side Trips

Brandon, Warren, Addison, Waitsfield, Ripton
Highlights from your plan
Lincoln Peak Vineyard ©
Lincoln Peak Vineyard
Lake Champlain Maritime Museum ©
Lake Champlain Maritime Museum
Vermont Marble Museum ©
Vermont Marble Museum

13
nights
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. Your inner history buff will appreciate Billings Farm & Museum and Marsh - Billings - Rockefeller National Historical Park. Give yourself a bit of retail therapy at Pierce's Store and Quechee Gorge Village Vermont Antique Mall. You'll find plenty of places to visit near Woodstock: Rutland (Deer Leap Trail & Pico Mountain), Ludlow (Okemo Mountain Resort & Healdville Trail) and Morrill Homestead (in Strafford). There's lots more to do: get curious at Montshire Museum of Science, identify plant and animal life at New England Falconry, fly down the slopes at Killington Resort, and indulge your thirst for a good beer at Long Trail Brewing Company.

To find ratings, other places to visit, where to stay, and other tourist information, read our Woodstock holiday planner .

Drive from Middlebury to Woodstock in 1.5 hours. In May, plan for daily highs up to 70°F, and evening lows to 45°F. Wrap up your sightseeing on the 9th (Sun) to allow time to drive to Manchester.

Things to do in Woodstock

Parks Outdoors Nature

Side Trips

Quechee, Windsor, Plymouth, Ludlow, Rutland
Highlights from your plan
Billings Farm & Museum ©
Billings Farm & Museum
Quechee Gorge ©
Quechee Gorge

11
nights
Manchester

Manchester ©
Manchester is a town in, and one of two shire towns (county seats) of, Bennington County, Vermont, United States. Visiting Mount Snow Resort and Jamaica State Park will get you outdoors. Do your shopping at Vermont Country Store and Jud Hartmann Gallery. Venture out of the city with trips to Rockingham Meeting House (in Rockingham), Gallery North Star (in Grafton) and Chester (Stone House Antique Center & DaVallia Art & Accents). On the 14th (Fri), spend an exhilarating day on the slopes at Stratton Mountain. There's still lots to do: take in nature's colorful creations at Hildene, The Lincoln Family Home, view the masterpieces at The Art of Humor Gallery, learn about winemaking at Putney Mountain Winery, and brush up on your knowledge of spirits at Saxtons River Distillery.

For other places to visit, maps, more things to do, and other tourist information, you can read our Manchester road trip planning app .

Traveling by car from Woodstock to Manchester takes 2 hours. Alternatively, you can take a bus. In June in Manchester, expect temperatures between 76°F during the day and 53°F at night. Finish up your sightseeing early on the 20th (Thu) so you can go by car back home.

Things to do in Manchester

Parks Outdoors Museums

Side Trips

Brattleboro, Bennington, Grafton, Dover, Chester
Highlights from your plan
Hildene, The Lincoln Family Home ©
Hildene, The Lincoln Family Home
Vermont Country Store ©
Vermont Country Store
Bennington Museum ©
Bennington Museum

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