14 days in Vermont Itinerary

14 days in Vermont Itinerary

Created using Inspirock Vermont trip itinerary planner
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Make it your trip
Fly to Logan International Airport, Drive to Wilmington
1
Wilmington
— 2 nights
Drive
2
Jamaica
— 1 night
Drive
3
Weston
— 1 night
Drive
4
Plymouth
— 1 night
Drive
5
Killington
— 3 nights
Drive
6
Stowe
— 5 nights
Drive

S M T W T F S
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1

Wilmington — 2 nights

Wilmington is a town in Windham County, Vermont, United States. Kick off your visit on the 18th (Sun): relax and rejuvenate at Serenity Spa and then contemplate the long history of Hildene, The Lincoln Family Home. Here are some ideas for day two: see the interesting displays at Shelburne Falls Trolley Museum, whizz through the canopy at some of the top local zipline courses and adventure parks, and then snap pictures at Bridge of Flowers.

For traveler tips, maps, reviews, and other tourist information, use the Wilmington visit planner.

Kalamazoo to Wilmington is an approximately 9.5-hour combination of flight and car. You can also drive. Traveling from Kalamazoo in June, Wilmington is slightly colder at night with lows of 54°F. On the 20th (Tue), you'll travel to Jamaica.
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Adventure · Tours · Outdoors · Museums
Side Trips
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Jamaica — 1 night

Jamaica is a town in Windham County, Vermont, United States. Start off your visit on the 20th (Tue): shop like a local with Jud Hartmann Gallery and then immerse yourself in nature at Jamaica State Park.

For ratings, other places to visit, photos, and tourist information, go to the Jamaica journey planner.

Drive from Wilmington to Jamaica in an hour. In June in Jamaica, expect temperatures between 76°F during the day and 52°F at night. You'll set off for Weston on the 21st (Wed).
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Shopping · Nature · Parks · Museums
Side Trip
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Highlights from your trip

Weston — 1 night

Weston is a town in Windsor County, Vermont, United States. Start off your visit on the 21st (Wed): take your sightseeing to a higher altitude at Bromley Mountain and then contemplate in the serene atmosphere at Weston Priory.

To see other places to visit, photos, maps, and tourist information, refer to the Weston trip builder tool.

Weston is just a stone's throw from Jamaica. June in Weston sees daily highs of 76°F and lows of 52°F at night. Wrap up your sightseeing by early afternoon on the 22nd (Thu) to allow time for the car ride to Plymouth.
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Historic Sites · Shopping · Winter Sports · Outdoors
Side Trip
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Plymouth — 1 night

Plymouth is a town in Windsor County, Vermont, United States. Start your trip to Plymouth by creating a personalized itinerary on Inspirock.

Traveling by car from Weston to Plymouth takes an hour. In June, daily temperatures in Plymouth can reach 74°F, while at night they dip to 54°F. Finish your sightseeing early on the 23rd (Fri) to allow enough time to drive to Killington.
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Historic Sites
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Killington — 3 nights

Killington is a town in Rutland County, Vermont, United States. Venture out of the city with trips to Quechee Gorge (in Quechee), Lincoln (Off-Road Tours & Flume Gorge) and Whiteface Mountain (in Wilmington). There's much more to do: fly down the slopes at Killington Resort, tour the pleasant surroundings at Thundering Brook Falls Trail, and admire the majestic nature at Gifford Woods State Park.

For more things to do and tourist information, you can read our Killington trip itinerary maker tool.

Killington is very close to Plymouth. In June, plan for daily highs up to 74°F, and evening lows to 54°F. Finish your sightseeing early on the 26th (Mon) so you can drive to Stowe.
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Parks · Outdoors · Nature · Winter Sports
Side Trips
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Stowe — 5 nights

The Ski Capital of the East

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.
Venture out of the city with trips to Franconia (The Basin at Franconia Notch State Park & Franconia Notch State Park) and Burlington (Vermont Farm Tours, Burlington Bike Path, &more). There's still lots to do: trek along Stowe Recreation Path, explore the activities along Mad River, cruise along Smugglers Notch State Park, and shop like a local with Nebraska Knoll Sugar Farm.

To see photos, maps, other places to visit, and other tourist information, you can read our Stowe itinerary maker site.

Traveling by car from Killington to Stowe takes 1.5 hours. Alternatively, you can take a bus. June in Stowe sees daily highs of 74°F and lows of 51°F at night. Finish your sightseeing early on the 1st (Sat) to allow enough time to drive back home.
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Parks · Nature · Outdoors · Trails
Side Trips
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Vermont travel guide

4.5
The Green Mountain State
Known for its autumn foliage and maple syrup, Vermont is one of the country's smallest states in terms of both population and geographic area. Despite its small size and mostly rural character, the state boasts many picturesque places to visit, including Lake Champlain, one of the nation's largest freshwater bodies. Split in half by the Green Mountains--a popular holiday destination for hiking and skiing--Vermont features a rolling landscape dotted with farms and quaint towns known for their family-run inns, antique shops, and restaurants. Be sure to explore the state's many wild areas while on vacation, but beware of the so-called "mud season," a period of a few weeks when the state's unpaved roads become undrivable due to spring thaw.
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