12 days in New England Itinerary

12 days in New England Itinerary

Created using Inspirock New England itinerary maker

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Route & dates

12 days in New England Itinerary

Start: Rochester
Drive:  5​h 15​min
1
Manchester
— 2 nights
Drive:  1​h 45​min
2
Woodstock
— 1 night
Drive:  2​h
3
Moultonborough
— 2 nights
Drive:  1​h 45​min
4
Portland
— 2 nights
Drive:  45​min
5
Ogunquit
— 2 nights
Drive:  30​min
6
Portsmouth
— 2 nights
+2
bus + foot + Fly:  4​h 45​min
End: Rochester

2
nights
Manchester

Manchester ©
Manchester is a town in, and one of two shire towns (county seats) of, Bennington County, Vermont, United States. Kick off your visit on the 19th (Sat): explore the world behind art at Williams College Museum of Art, stroll the grounds of The Old First Church, and then take your sightseeing to a higher altitude at Equinox Mountain. Get ready for a full day of sightseeing on the 20th (Sun): admire the sheer force of Lye Brook Falls, then snap pictures at Silk Road Covered Bridge, then stop by Manchester Hot Glass, and finally identify plant and animal life at Equinox Preservation Trust.

For photos, traveler tips, reviews, and other tourist information, read Manchester trip itinerary builder website .

Rochester to Manchester is an approximately 5.5-hour car ride. You can also do a combination of train and bus; or do a combination of flight and bus. Expect a daytime high around 62°F in October, and nighttime lows around 41°F. Cap off your sightseeing on the 21st (Mon) early enough to go by car to Woodstock.

Things to do in Manchester

Parks Nature Wildlife

Side Trips

Bennington, Equinox Mountain, Williams College Museum of Art
Highlights from your plan
The Old First Church ©
The Old First Church
Manchester Hot Glass ©
Manchester Hot Glass
Williams College Museum of Art ©
Williams College Museum of Art

1
night
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. On the 21st (Mon), contemplate the long history of Calvin Coolidge Homestead, sample the tasty concoctions at Long Trail Brewing Company, then contemplate the waterfront views at Ottaquechee River, and finally take in the views from Taftsville Covered Bridge. Get ready for a full day of sightseeing on the next day: brush up on your knowledge of spirits at Vermont Spirits, stop by Dan & Whit's General Store, then take in the views from Cornish-Windsor Bridge, and finally take your sightseeing to a higher altitude at Mount Tom.

To find photos, other places to visit, where to stay, and tourist information, read our Woodstock trip planning site .

Traveling by car from Manchester to Woodstock takes 2 hours. Alternatively, you can take a bus. In October, daytime highs in Woodstock are 62°F, while nighttime lows are 40°F. Finish up your sightseeing early on the 22nd (Tue) so you can go by car to Moultonborough.

Things to do in Woodstock

Parks Nature Breweries & Distilleries

Side Trips

Vermont Spirits, Cornish-Windsor Bridge, Dan & Whit's General Store, Long Trail Brewing Company, Calvin Coolidge Homestead
Highlights from your plan
Calvin Coolidge Homestead ©
Calvin Coolidge Homestead
Long Trail Brewing Company ©
Long Trail Brewing Company
Mount Tom ©
Mount Tom

2
nights
Moultonborough

Moultonborough ©
Moultonborough is a town in Carroll County, New Hampshire, United States. Start off your visit on the 23rd (Wed): examine the collection at Remick Country Doctor Museum & Farm, then take in the awesome beauty at Mt Chocorua, then take in the architecture and atmosphere at The Little White Church, and finally learn about winemaking at Sap House Meadery. Here are some ideas for day two: learn about winemaking at Black Bear Vineyard, then look for gifts at Innisfree Bookshop, and then explore the activities along Lake Chocorua.

To see where to stay, reviews, ratings, and other tourist information, go to the Moultonborough road trip planning website .

Getting from Woodstock to Moultonborough by car takes about 2 hours. In October in Moultonborough, expect temperatures between 60°F during the day and 42°F at night. Wrap up your sightseeing on the 24th (Thu) to allow time to drive to Portland.

Things to do in Moultonborough

Parks Nature Wineries

Side Trips

Chocorua, Remick Country Doctor Museum & Farm, The Little White Church, Sap House Meadery, Innisfree Bookshop
Highlights from your plan
Lake Chocorua ©
Lake Chocorua
Remick Country Doctor Museum & Farm ©
Innisfree Bookshop ©
Innisfree Bookshop

2
nights
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.
Start off your visit on the 25th (Fri): contemplate the long history of Wadsworth-Longfellow House, indulge your thirst for a good beer at Maine Beer Company, then take a memorable drive along Coastal Highway U.S. 1, and finally indulge your thirst for a good beer at Rising Tide Brewing Company. On the next day, look for gifts at Len Libby Chocolates, then go for a walk through Cliff Walk, then tour the pleasant surroundings at Higgins Beach, and finally enjoy the sea views from Portland Breakwater Lighthouse.

To see reviews, where to stay, more things to do, and tourist information, go to the Portland road trip planning site .

You can drive from Moultonborough to Portland in 2 hours. Expect a daytime high around 62°F in October, and nighttime lows around 43°F. Wrap up your sightseeing on the 26th (Sat) early enough to drive to Ogunquit.

Things to do in Portland

Outdoors Historic Sites Parks

Side Trips

Scarborough, Cliff Walk, Coastal Highway U.S. 1, Maine Beer Company, Portland Breakwater Lighthouse
Highlights from your plan
Wadsworth-Longfellow House ©
Wadsworth-Longfellow House
Higgins Beach ©
Higgins Beach
Maine Beer Company ©
Maine Beer Company

2
nights
Ogunquit

Ogunquit ©
Ogunquit means "beautiful place by the sea" in the language of the Native Americans who inhabited the region long ago, and this remains an accurate description of this holiday destination today.
Start off your visit on the 27th (Sun): enjoy the sand and surf at Kennebunk Beach, then enjoy the sand and surf at Footbridge Beach, and then browse for treasures at Uniques and Antiques. Here are some ideas for day two: take your sightseeing to a higher altitude at Mount Agamenticus, take in the views from Wiggly Bridge and Steedman Woods, then stop by Stonewall Kitchen, and finally view the masterpieces at Abacus.

For maps, more things to do, photos, and other tourist information, go to the Ogunquit day trip tool .

Drive from Portland to Ogunquit in an hour. Alternatively, you can do a combination of bus and taxi; or take a train. Traveling from Portland in October, you can expect nighttime temperatures to be little chillier in Ogunquit, with lows of 38°F. Wrap up your sightseeing on the 28th (Mon) to allow time to drive to Portsmouth.

Things to do in Ogunquit

Parks Outdoors Beaches

Side Trips

York, Kennebunk Beach, Wiggly Bridge and Steedman Woods
Highlights from your plan
Mount Agamenticus ©
Mount Agamenticus
Abacus ©
Abacus
Stonewall Kitchen ©
Stonewall Kitchen

2
nights
Portsmouth

Portsmouth ©
Portsmouth is a city in Rockingham County, New Hampshire, in the United States. Kick off your visit on the 29th (Tue): kick back and relax at Salisbury Beach State Reservation, then admire nature's wide array of creatures at Blue Ocean Discovery Center, then admire the natural beauty at Moffatt-Ladd House & Garden, and finally take in nature's colorful creations at Hamilton House. Here are some ideas for day two: enjoy the sand and surf at Front Beach, then indulge your thirst for a good beer at Smuttynose Brewing, then look for gifts at Yummies Candy and Nuts, and finally indulge your thirst for a good beer at Tributary Brewing.

To find more things to do, traveler tips, and more tourist information, read Portsmouth vacation app .

Portsmouth is just a stone's throw from Ogunquit. Traveling from Ogunquit in October, expect a bit warmer with lows of 44°F in Portsmouth. Finish your sightseeing early on the 30th (Wed) to allow enough time to travel back home.

Things to do in Portsmouth

Parks Outdoors Beaches

Side Trips

Kittery, Hampton, Salisbury Beach State Reservation, Front Beach, Hamilton House
Highlights from your plan
Hamilton House ©
Hamilton House
Front Beach ©
Front Beach
Smuttynose Brewing ©
Smuttynose Brewing

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