9 days in New England Itinerary

9 days in New England Itinerary

Created using Inspirock United States itinerary planner

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Route & dates

9 days in New England Itinerary

Start: Rochester
Drive:  5​h
1
Manchester
— 1 night
Drive:  4​h 30​min
2
Portland
— 2 nights
Drive:  45​min
3
Kennebunkport
— 1 night
Drive:  30​min
4
Ogunquit
— 1 night
Drive:  30​min
5
Portsmouth
— 1 night
Drive:  1​h 15​min
6
Gloucester
— 2 nights
Fly:  5​h 30​min
End: Rochester

1
night
Manchester

Manchester ©
Manchester is a town in, and one of two shire towns (county seats) of, Bennington County, Vermont, United States. Start off your visit on the 19th (Sat): identify plant and animal life at Equinox Preservation Trust, admire the natural beauty at Hildene, The Lincoln Family Home, then take in the dramatic scenery at Lye Brook Falls, and finally admire all the interesting features of North Meadow Farm.

For maps, more things to do, and more tourist information, go to the Manchester online route planner .

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. Finish your sightseeing early on the 20th (Sun) so you can drive to Portland.

Things to do in Manchester

Parks Wildlife Nature
Highlights from your plan
Hildene, The Lincoln Family Home ©
Hildene, The Lincoln Family Home
Equinox Preservation Trust ©
Equinox Preservation Trust
North Meadow Farm ©
North Meadow Farm

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.
Your day-by-day itinerary now includes Maine Foodie Tours as well as Wicked Walking Tours. Get some cultural insight at Portland Head Light and Old Port. Change things up with a short trip to Pemaquid Point Lighthouse in Bristol (about 1h 15 min away). There's still lots to do: indulge your thirst for a good beer at Allagash Brewery, kick back and relax at Old Orchard Beach, take an in-depth tour of Victoria Mansion, and admire the masterpieces at Portland Museum of Art.

To find traveler tips, more things to do, other places to visit, and other tourist information, use the Portland online vacation builder .

Getting from Manchester to Portland by car takes about 4.5 hours. Other options: do a combination of bus and flight; or take a bus. October in Portland sees daily highs of 62°F and lows of 43°F at night. Finish your sightseeing early on the 22nd (Tue) so you can drive to Kennebunkport.

Things to do in Portland

Tours Nightlife Museums

Side Trips

Pemaquid Point Lighthouse, Portland Head Light, Old Orchard Beach
Highlights from your plan
Wicked Walking Tours ©
Wicked Walking Tours
Pemaquid Point Lighthouse ©
Pemaquid Point Lighthouse
Portland Head Light ©
Portland Head Light

1
night
Kennebunkport

Kennebunkport ©
Kennebunkport is a town in York County, Maine, United States. Kick off your visit on the 22nd (Tue): take in the architecture and atmosphere at St. Ann's Episcopal Church.

For reviews, more things to do, photos, and more tourist information, refer to the Kennebunkport trip site .

You can drive from Portland to Kennebunkport in an hour. Alternatively, you can take a bus; or do a combination of train and bus. Traveling from Portland in October, Kennebunkport is a bit cooler at night with lows of 38°F. Finish your sightseeing early on the 23rd (Wed) to allow enough time to drive to Ogunquit.

Things to do in Kennebunkport

Outdoors Parks Beaches
Highlights from your plan
St. Ann's Episcopal Church ©
St. Ann's Episcopal Church

1
night
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.
For more things to do, traveler tips, maps, and more tourist information, you can read our Ogunquit trip itinerary builder app .

Ogunquit is just a stone's throw from Kennebunkport. Expect a daytime high around 62°F in October, and nighttime lows around 38°F. You will leave for Portsmouth on the 24th (Thu).

Things to do in Ogunquit

Outdoors Parks Tours

1
night
Portsmouth

Portsmouth ©
Portsmouth is a city in Rockingham County, New Hampshire, in the United States. On the 24th (Thu), don't miss a visit to Market Square, examine the collection at USS Albacore Museum, then look for gifts at Kittery Trading Post, and finally kick back and relax at Hampton Beach State Park.

To see maps, other places to visit, and tourist information, read Portsmouth online trip itinerary maker .

Portsmouth is very close to Ogunquit. Traveling from Ogunquit in October, plan for a bit warmer nights in Portsmouth, with lows around 44°F. Wrap up your sightseeing by early afternoon on the 25th (Fri) to allow enough time to drive to Gloucester.

Things to do in Portsmouth

Museums Outdoors Parks

Side Trips

Kittery Trading Post, Hampton Beach State Park, Portsmouth Harbor Lighthouse
Highlights from your plan
Strawbery Banke Museum ©
Strawbery Banke Museum
Hampton Beach State Park ©
Hampton Beach State Park
Portsmouth Harbor Lighthouse ©
Portsmouth Harbor Lighthouse

2
nights
Gloucester

Gloucester ©
The still waters off the Gloucester shore are immortalized in paintings and prints produced by the hundreds of artists who visit this town.
Kick off your visit on the 25th (Fri): stroll the grounds of Old First Parish Burying Ground and then step into the grandiose world of Hammond Castle. Keep things going the next day: enjoy the sand and surf at Good Harbor Beach, then get great views at Bearskin Neck, and then identify plant and animal life at Halibut Point State Park.

For where to stay, reviews, more things to do, and tourist information, refer to the Gloucester trip itinerary planner.

You can drive from Portsmouth to Gloucester in 1.5 hours. Alternatively, you can do a combination of bus and train. In October in Gloucester, expect temperatures between 64°F during the day and 45°F at night. On the 27th (Sun), you'll have the morning to explore before heading back home.

Things to do in Gloucester

Parks Wildlife Nature

Side Trip

Rockport
Highlights from your plan
Good Harbor Beach ©
Good Harbor Beach
Halibut Point State Park ©
Halibut Point State Park
Hammond Castle ©
Hammond Castle

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