8 days in New England Itinerary

8 days in New England Itinerary

Created using Inspirock New England trip builder

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Route & dates

8 days in New England Itinerary

Start: Chicago
Fly:  4​h
1
Boston
— 2 nights
Drive:  1​h 30​min
2
Ogunquit
— 1 night
Drive:  2​h
3
Boothbay Harbor
— 2 nights
Drive:  4​h 30​min
4
Falmouth
— 2 nights
bus + Fly:  6​h 30​min
End: Chicago

2
nights
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.
Deepen your sense of the past at sights like Freedom Trail and Louisa May Alcott's Orchard House. Take a break from Boston with a short trip to Dolphin & Whale Watching in Gloucester, about 50 minutes away. Next up on the itinerary: admire the masterpieces at Museum of Fine Arts, stroll the grounds of Mount Auburn Cemetery, admire the natural beauty at Boston Public Garden, and contemplate the long history of Granary Burying Ground.

To find traveler tips, photos, where to stay, and tourist information, use the Boston road trip planning tool .

Chicago to Boston is an approximately 4-hour flight. You can also do a combination of flight and bus; or drive. Traveling from Chicago to Boston, you'll lose 1 hour due to the time zone difference. In October in Boston, expect temperatures between 64°F during the day and 50°F at night. Wrap up your sightseeing on the 21st (Mon) to allow time to drive to Ogunquit.

Things to do in Boston

Historic Sites Museums Wildlife

Side Trips

Cambridge, Dolphin & Whale Watching, Louisa May Alcott's Orchard House
Highlights from your plan
Dolphin & Whale Watching
Freedom Trail ©
Freedom Trail
Louisa May Alcott's Orchard House ©
Louisa May Alcott's Orchard House

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.
On the 22nd (Tue), look for all kinds of wild species at Wells Reserve at Laudholm, visit a coastal fixture at Cape Neddick Nubble Lighthouse, and then get to know the fascinating history of Marginal Way Walkway.

To find more things to do, photos, maps, and tourist information, refer to the Ogunquit travel route planner .

You can drive from Boston to Ogunquit in 1.5 hours. Alternatively, you can take a train; or take a bus. Expect slightly colder evenings in Ogunquit when traveling from Boston in October, with lows around 38°F. Wrap up your sightseeing on the 22nd (Tue) early enough to drive to Boothbay Harbor.

Things to do in Ogunquit

Historic Sites Parks Wildlife

Side Trips

Nubble Lighthouse, Wells Reserve at Laudholm
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Nubble Lighthouse ©
Nubble Lighthouse
Wells Reserve at Laudholm ©
Wells Reserve at Laudholm

2
nights
Boothbay Harbor

Boothbay Harbor ©
Boothbay Harbor is a town in Lincoln County, Maine, United States. Start off your visit on the 23rd (Wed): contemplate the long history of The Wilson Memorial Chapel, then visit a coastal fixture at Pemaquid Point Lighthouse, then admire the engineering at The Swimming Hole At Bristol Dam, and finally identify plant and animal life at Boothbay Region Land Trust. Here are some ideas for day two: take in nature's colorful creations at Coastal Maine Botanical Gardens and then identify plant and animal life at Todd Audubon Sanctuary at Hog Island.

To find maps, traveler tips, ratings, and tourist information, read our Boothbay Harbor trip planner.

You can drive from Ogunquit to Boothbay Harbor in 2 hours. Other options are to do a combination of train and taxi; or do a combination of bus and taxi. Expect a daytime high around 61°F in October, and nighttime lows around 41°F. Finish your sightseeing early on the 24th (Thu) so you can drive to Falmouth.

Things to do in Boothbay Harbor

Parks Wildlife Historic Sites

Side Trips

Boothbay, Bristol, Todd Audubon Sanctuary at Hog Island
Highlights from your plan
Boothbay Region Land Trust ©
Boothbay Region Land Trust
Pemaquid Point Lighthouse ©
Pemaquid Point Lighthouse
Todd Audubon Sanctuary at Hog Island ©

2
nights
Falmouth

Falmouth ©
Falmouth is a town in Barnstable County, Massachusetts, United States; Barnstable County is coextensive with Cape Cod. Start off your visit on the 25th (Fri): look for all kinds of wild species at East Over Reservation, then explore the activities along Cape Cod Canal, then steep yourself in history at Edward Gorey House, and finally explore and take pictures at Cornelia Carey Sanctuary (The Knob). Get ready for a full day of sightseeing on the next day: engage your brain at Sandwich Glass Museum, then see the interesting displays at Heritage Museums & Gardens, then explore the landscape on two wheels at Shining Sea Bikeway, and finally enjoy the sea views from Nobska Point Lighthouse.

To see more things to do, maps, and other tourist information, you can read our Falmouth road trip planner.

You can drive from Boothbay Harbor to Falmouth in 4.5 hours. Alternatively, you can do a combination of flight and bus; or do a combination of taxi, flight, and bus. In October, daytime highs in Falmouth are 64°F, while nighttime lows are 46°F. Finish up your sightseeing early on the 26th (Sat) so you can travel back home.

Things to do in Falmouth

Parks Museums Historic Sites

Side Trips

Sandwich, Edward Gorey House, Cape Cod Canal, East Over Reservation
Highlights from your plan
East Over Reservation ©
East Over Reservation
Edward Gorey House ©
Edward Gorey House
Cornelia Carey Sanctuary (The Knob) ©

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