10 days in New England Itinerary

10 days in New England Itinerary

Created using Inspirock New England journey planner

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Route & dates

10 days in New England Itinerary

Start: Chicago
Fly:  6​h 15​min
1
New Haven
— 1 night
Drive:  2​h 15​min
2
Newport
— 1 night
Drive:  1​h 30​min
3
Boston
— 2 nights
4
Portland
— 2 nights
Drive:  1​h 45​min
5
North Conway
— 1 night
Drive:  1​h 15​min
6
Lincoln
— 1 night
Drive:  2​h 30​min
7
Burlington
— 1 night
Fly:  4​h 15​min
End: Chicago

1
night
New Haven

New Haven ©
New Haven, in the U.S. Kick off your visit on the 26th (Sat): gain insight at Yale University, get lost in a book at Beinecke Rare Book & Manuscript Library, then admire the masterpieces at Yale University Art Gallery, and finally snap pictures at Pearl Harbor Memorial Bridge.

To see more things to do, photos, where to stay, and other tourist information, read our New Haven trip builder tool .

Chicago to New Haven is an approximately 6.5-hour flight. You can also do a combination of flight and train; or drive. Due to the time zone difference, you'll lose 1 hour traveling from Chicago to New Haven. In September, daily temperatures in New Haven can reach 77°F, while at night they dip to 59°F. Finish your sightseeing early on the 26th (Sat) so you can drive to Newport.

Things to do in New Haven

Museums
Find places to stay Sep 25 — 26:
Highlights from your plan
Yale University Art Gallery ©
Yale University Art Gallery
Beinecke Rare Book & Manuscript Library ©
Yale University ©
Yale University

1
night
Newport

Newport ©
With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Start off your visit on the 27th (Sun): cruise along Ocean Drive Historic District, then see the interesting displays at The Breakers, and then get to know the fascinating history of Cliff Walk.

To see reviews, traveler tips, more things to do, and tourist information, read our Newport trip itinerary builder site .

Traveling by car from New Haven to Newport takes 2.5 hours. Alternatively, you can take a train; or take a bus. Expect a daytime high around 74°F in September, and nighttime lows around 58°F. Finish your sightseeing early on the 27th (Sun) to allow enough time to drive to Boston.

Things to do in Newport

Historic Sites Outdoors Parks
Find places to stay Sep 26 — 27:
Highlights from your plan
The Breakers ©
The Breakers
Ocean Drive Historic District ©
Ocean Drive Historic District

2
nights
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.
Start off your visit on the 28th (Mon): explore the world behind art at Museum of Fine Arts, take in nature's colorful creations at Boston Public Garden, and then appreciate the extensive heritage of Freedom Trail. On the next day, take a stroll through North End, explore the different monuments and memorials at Granary Burying Ground, stroll around Boston Common, then get a new perspective on things with Boat Tours & Water Sports, and finally browse the different shops at Faneuil Hall Marketplace.

To see other places to visit, reviews, maps, and tourist information, go to the Boston trip planner.

Drive from Newport to Boston in 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. In September in Boston, expect temperatures between 75°F during the day and 59°F at night. Finish up your sightseeing early on the 29th (Tue) so you can go by car to Portland.

Things to do in Boston

Parks Historic Sites Museums
Find places to stay Sep 27 — 29:
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Boston Public Garden ©
Boston Public Garden
Freedom Trail ©
Freedom Trail

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.
On the 30th (Wed), see the interesting displays at Portland Head Light, appreciate the extensive heritage of Marginal Way Walkway, and then sample the tasty concoctions at Allagash Brewing Company. Keep things going the next day: explore the world behind art at Portland Museum of Art, kick back and relax at Ogunquit Beach, and then take in the dramatic natural features at Perkins Cove.

For more things to do, photos, ratings, and other tourist information, read our Portland trip itinerary maker tool .

Getting from Boston to Portland by car takes about 2 hours. Other options: take a bus; or take a train. Traveling from Boston in September, plan for slightly colder nights in Portland, with lows around 52°F. Finish up your sightseeing early on the 1st (Thu) so you can go by car to North Conway.

Things to do in Portland

Parks Historic Sites Beaches

Side Trips

Ogunquit, Portland Head Light
Find places to stay Sep 29 — Oct 1:
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Portland Head Light ©
Portland Head Light
Perkins Cove ©
Perkins Cove

1
night
North Conway

North Conway ©
North Conway combines colonial New England architecture with outlet shops selling goods from some of the world's most recognizable brands, all set amid the scenery of the White Mountains.
Start off your visit on the 2nd (Fri): take in the dramatic scenery at Glen Ellis Falls, then see the sky in a new way at Mount Washington Observatory Weather Discovery Center, and then explore and take pictures at Kancamagus Highway.

To see ratings, where to stay, other places to visit, and tourist information, go to the North Conway trip itinerary app .

Traveling by car from Portland to North Conway takes 2 hours. Alternatively, you can do a combination of bus and taxi. In October, daily temperatures in North Conway can reach 62°F, while at night they dip to 45°F. Cap off your sightseeing on the 2nd (Fri) early enough to go by car to Lincoln.

Things to do in North Conway

Outdoors Scenic Drive Parks

Side Trip

Glen Ellis Falls
Find places to stay Oct 1 — 2:
Highlights from your plan
Kancamagus Highway ©
Kancamagus Highway
Glen Ellis Falls ©
Glen Ellis Falls

1
night
Lincoln

Lincoln ©
Stretching through the White Mountain National Forest, Lincoln welcomes hikers along the Appalachian Trail.
On the 3rd (Sat), get to know the fascinating history of Flume Gorge, then admire the majestic nature at Franconia Notch State Park, and then whizz through the canopy at some of the top local zipline courses and adventure parks.

To see more things to do, traveler tips, maps, and more tourist information, use the Lincoln online trip planner .

Drive from North Conway to Lincoln in 1.5 hours. Alternatively, you can take a bus. Traveling from North Conway in October, plan for slightly colder nights in Lincoln, with lows around 38°F. Finish your sightseeing early on the 3rd (Sat) so you can drive to Burlington.

Things to do in Lincoln

Parks Nature Historic Sites

Side Trip

Franconia
Find places to stay Oct 2 — 3:
Highlights from your plan
Franconia Notch State Park ©
Franconia Notch State Park
Flume Gorge ©
Flume Gorge

1
night
Burlington

Burlington ©
Burlington is the most populous city in the U.S. Kick off your visit on the 4th (Sun): trek along Burlington Bike Path, then shop like a local with Church Street Marketplace, and then examine the collection at Shelburne Museum.

Plan trip to Burlington with our itinerary maker to find out where to go and what to do.

Getting from Lincoln to Burlington by car takes about 2.5 hours. Other options: do a combination of car and bus; or take a bus. Plan for somewhat warmer nights when traveling from Lincoln in October since evenings lows in Burlington dip to 44°F. Finish your sightseeing early on the 4th (Sun) so you can travel back home.

Things to do in Burlington

Parks Trails Shopping

Side Trip

Shelburne Museum
Find places to stay Oct 3 — 4:
Highlights from your plan
Burlington Bike Path ©
Burlington Bike Path
Shelburne Museum ©
Shelburne Museum
Church Street Marketplace ©
Church Street Marketplace

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