8 days in United States Itinerary

8 days in United States Itinerary

Created using Inspirock United States journey planner

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Route & dates

8 days in United States Itinerary

Start: Boston
1
Boston
— 1 night
Drive:  2​h 30​min
2
Provincetown
— Few hours
Drive:  5​h
3
Woodstock
— 2 nights
Drive:  2​h
4
Stowe
— 1 night
Drive:  2​h 30​min
5
Jackson
— 1 night
Drive:  2​h
6
Portland
— 1 night
Drive:  1​h
7
Portsmouth
— 1 night
Drive:  1​h
8
Salem
— Few hours
Drive:  30​min
End: Boston

1
night
Boston

Boston ©
Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
Your list of things to see and do now includes The Point, North End, Harpoon Brewery & Beer Hall, and other attractions. Kick off your visit on the 14th (Mon): indulge your thirst for a good beer at Harpoon Brewery & Beer Hall, indulge your thirst for a good beer at Samuel Adams Brewery, appreciate the extensive heritage of Freedom Trail, then wander the streets of North End, and finally join in the after-dark buzz at The Point.

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

The Route module can give you travel options from your home to Boston. October in Boston sees daily highs of 64°F and lows of 50°F at night. You will have some time to spend on the 15th (Tue) before leaving for Provincetown.

Things to do in Boston

Breweries & Distilleries Historic Sites Neighborhoods
Highlights from your plan
Freedom Trail ©
Freedom Trail
North End ©
North End
Harpoon Brewery & Beer Hall ©
Harpoon Brewery & Beer Hall

few
hours
Provincetown

Provincetown
A small resort town with a year-round population of just 3,000, Provincetown draws nearly 60,000 annual visitors with its scenic beaches, art colonies, galleries, theaters, and shops.
To see traveler tips, photos, reviews, and more tourist information, refer to the Provincetown day trip planning tool .

You can ride a ferry from Boston to Provincetown in 1.5 hours. Alternatively, you can fly; or drive. In October, daytime highs in Provincetown are 63°F, while nighttime lows are 49°F. You'll set off for Woodstock on the 15th (Tue).

Things to do in Provincetown

Outdoors Parks Tours

2
nights
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. Kick off your visit on the 15th (Tue): contemplate the long history of Calvin Coolidge Homestead.

For other places to visit, traveler tips, more things to do, and more tourist information, you can read our Woodstock vacation builder website .

Traveling by combination of flight and taxi from Provincetown to Woodstock takes 4 hours. Alternatively, you can drive. Traveling from Provincetown in October, Woodstock is slightly colder at night with lows of 40°F. On the 17th (Thu), you're off toStowe.

Things to do in Woodstock

Nature Parks Historic Sites

Side Trips

Calvin Coolidge Homestead, Cornish-Windsor Bridge
Highlights from your plan
Mount Tom ©
Mount Tom
Cornish-Windsor Bridge ©
Cornish-Windsor Bridge
Taftsville Covered Bridge ©
Taftsville Covered Bridge

1
night
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.
Kick off your visit on the 17th (Thu): indulge your thirst for a good beer at Rock Art Brewery and then stroll through Stowe Recreation Path.

To find photos, ratings, traveler tips, and more tourist information, use the Stowe trip itinerary maker website .

Traveling by car from Woodstock to Stowe takes 2 hours. Alternatively, you can take a train; or take a bus. October in Stowe sees daily highs of 60°F and lows of 39°F at night. You'll have a few hours on the 18th (Fri) to wrap things up before traveling to Jackson.

Things to do in Stowe

Trails Parks Outdoors

Side Trips

Ziemke Glass Blowing Studio, Rock Art Brewery
Highlights from your plan
Stowe Recreation Path ©
Stowe Recreation Path
Ziemke Glass Blowing Studio ©
Ziemke Glass Blowing Studio
Rock Art Brewery ©
Rock Art Brewery

1
night
Jackson

Jackson ©
Jackson is a town in Carroll County, New Hampshire, United States. On the 18th (Fri), look and learn at Mount Washington Observatory Weather Discovery Center and then admire the sheer force of Echo Lake State Park.

To find traveler tips, other places to visit, reviews, and other tourist information, use the Jackson trip itinerary website .

Drive from Stowe to Jackson in 2.5 hours. Traveling from Stowe in October, plan for somewhat warmer nights in Jackson, with lows around 45°F. On the 19th (Sat), you'll have the morning to explore before heading off to Portland.

Things to do in Jackson

Nature Parks Museums

Side Trips

Mount Washington Observatory Weather Discovery Center, Echo Lake State Park
Highlights from your plan
Echo Lake State Park ©
Echo Lake State Park
Jackson Art Studio & Gallery ©
Jackson Art Studio & Gallery

1
night
Portland

Portland ©
Maine's biggest and perhaps most vibrant city, Portland was established as a fishing village in 1633 and grew to become New England's largest port.
Kick off your visit on the 19th (Sat): contemplate the long history of Wadsworth-Longfellow House and then enjoy the sea views from Portland Breakwater Lighthouse.

For photos, traveler tips, more things to do, and more tourist information, go to the Portland sightseeing planner .

You can drive from Jackson to Portland in 2 hours. In October, daytime highs in Portland are 62°F, while nighttime lows are 43°F. On the 20th (Sun), you'll have the morning to explore before heading off to Portsmouth.

Things to do in Portland

Historic Sites Shopping

Side Trips

Len Libby Chocolates, Portland Breakwater Lighthouse
Highlights from your plan
Wadsworth-Longfellow House ©
Wadsworth-Longfellow House
Portland Breakwater Lighthouse ©
Portland Breakwater Lighthouse
Len Libby Chocolates ©
Len Libby Chocolates

1
night
Portsmouth

Portsmouth ©
Portsmouth is a city in Rockingham County, New Hampshire, in the United States. Start off your visit on the 20th (Sun): contemplate the long history of Strawbery Banke Museum, visit a coastal fixture at Portsmouth Harbor Lighthouse, and then admire the natural beauty at Hamilton House.

Planning Portsmouth trip won't be overwheling when you use's Insprock itinerary maker.

Getting from Portland to Portsmouth by car takes about an hour. Other options: take a bus. October in Portsmouth sees daily highs of 62°F and lows of 44°F at night. You will have some time to spend on the 21st (Mon) before leaving for Salem.

Things to do in Portsmouth

Historic Sites Museums Parks

Side Trips

Hamilton House, Portsmouth Harbor Lighthouse
Highlights from your plan
Strawbery Banke Museum ©
Strawbery Banke Museum
Portsmouth Harbor Lighthouse ©
Portsmouth Harbor Lighthouse
Hamilton House ©
Hamilton House

few
hours
Salem

Salem ©
Best known for its 1692 witch trials, Salem has a number of significant historical sites, a bustling downtown, and many witch-themed attractions.
Start off your visit on the 21st (Mon): stroll the grounds of Old Burying Point Cemetery, then get engrossed in the history at Salem Witch Museum, and then contemplate the long history of The House of the Seven Gables.

To see maps, where to stay, more things to do, and other tourist information, go to the Salem visit planner.

Traveling by car from Portsmouth to Salem takes an hour. Alternatively, you can do a combination of bus and train; or take a bus. In October, daily temperatures in Salem can reach 64°F, while at night they dip to 45°F. Wrap up your sightseeing on the 21st (Mon) early enough to drive back home.

Things to do in Salem

Historic Sites Museums
Highlights from your plan
The House of the Seven Gables ©
The House of the Seven Gables
Salem Witch Museum ©
Salem Witch Museum
Old Burying Point Cemetery ©
Old Burying Point Cemetery

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