10 days in New England Itinerary

10 days in New England Itinerary

Created using Inspirock New England journey planner

This plan was created by another user. Make it your plan

Route & dates

Start: Chicago
+2
Fly + Bus + Train:  6 h 15 min
1
New Haven
— 1 night
Drive:  2 h 15 min
2
Newport
— 1 night
Bus:  1 h 30 min
3
Boston
— 2 nights
Drive:  2 h
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 explore the world behind art at Yale University Art Gallery, and finally take in the views from Pearl Harbor Memorial Bridge.

To see other places to visit, photos, and more tourist information, use the New Haven day trip website.

Chicago to New Haven is an approximately 6.5- hour combination of flight and train. You can also do a combination of flight, bus, and train; or drive. The time zone changes from Central Standard Time to Eastern Standard Time, which is usually a 1 hour difference. September in New Haven sees daily highs of 77°F and lows of 59°F at night. Wrap up your sightseeing on the 26th (Sat) to allow time to 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 ©
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.
Kick off your visit on the 27th (Sun): cruise along Ocean Drive Historic District, see the interesting displays at The Breakers, and then appreciate the extensive heritage of Cliff Walk.

To see other places to visit, where to stay, traveler tips, and more tourist information, you can read our Newport tour itinerary planning site.

You can drive from New Haven to Newport in 2.5 hours. Alternatively, you can do a combination of train and bus; or take a bus. Expect a daytime high around 74°F in September, and nighttime lows around 58°F. Wrap up your sightseeing on the 27th (Sun) to allow time to take a bus to Boston.

Things to do in Newport

Historic Sites Outdoors Museums
Find places to stay Sep 26 — 27:
Highlights from your plan
The Breakers ©
The Breakers
Cliff Walk ©
Cliff Walk
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): admire the masterpieces at Museum of Fine Arts, admire the natural beauty at Boston Public Garden, and then get to know the fascinating history of Freedom Trail. Get ready for a full day of sightseeing on the next day: take a stroll through North End, then stroll the grounds of Granary Burying Ground, then stroll around Boston Common, and finally browse the different shops at Faneuil Hall Marketplace.

To find maps, reviews, and other tourist information, go to the Boston online route planner.

You can take a bus from Newport to Boston in 2 hours. Alternatively, you can drive; or do a combination of bus and train. September in Boston sees daily highs of 75°F and lows of 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

Museums Historic Sites Parks
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
Boston Common ©
Boston Common

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.
Kick off your visit on the 30th (Wed): enjoy the sea views from Portland Head Light, then appreciate the extensive heritage of Marginal Way Walkway, and then sample the tasty concoctions at Allagash Brewing Company. Get ready for a full day of sightseeing on the next day: explore the world behind art at Portland Museum of Art, enjoy the sand and surf at Ogunquit Beach, and then take in the dramatic natural features at Perkins Cove.

To see more things to do, maps, reviews, and tourist information, go to the Portland travel planning website.

Drive from Boston to Portland in 2 hours. Alternatively, you can take a bus; or take a train. Plan for little chillier nights when traveling from Boston in September since evenings lows in Portland dip to 52°F. Wrap up your sightseeing on the 1st (Thu) to allow time to drive to North Conway.

Things to do in Portland

Historic Sites Parks Museums

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.
On the 2nd (Fri), take in the dramatic scenery at Glen Ellis Falls, see the sky in a new way at Mount Washington Observatory Weather Discovery Center, and then cruise along Kancamagus Highway.

Ask Inspirock to suggest an itinerary and make planning a trip to North Conway fast, fun, and easy.

Traveling by car from Portland to North Conway takes 2 hours. Alternatively, you can do a combination of bus and taxi. In October, plan for daily highs up to 62°F, and evening lows 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

Scenic Drive Outdoors Nature

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.
Start off your visit on the 3rd (Sat): take in the dramatic scenery at Flume Gorge and then immerse yourself in nature at Franconia Notch State Park.

To find photos, other places to visit, more things to do, and more tourist information, use the Lincoln vacation planner.

Getting from North Conway to Lincoln by car takes about 1.5 hours. Other options: take a bus. Traveling from North Conway in October, Lincoln is a bit cooler at night with lows of 38°F. Finish up your sightseeing early on the 3rd (Sat) so you can go by car to Burlington.

Things to do in Lincoln

Nature Parks 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. Start off your visit on the 4th (Sun): hike along Burlington Bike Path, then browse the eclectic array of goods at Church Street Marketplace, and then examine the collection at Shelburne Museum.

To find photos, ratings, where to stay, and more tourist information, you can read our Burlington trip itinerary planning website.

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. Expect a bit warmer evenings in Burlington when traveling from Lincoln in October, with lows around 44°F. Finish your sightseeing early on the 4th (Sun) so you can travel back home.

Things to do in Burlington

Shopping Museums Outdoors

Side Trip

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

Similar Plans

37 days in United States BY A USER FROM AUSTRALIA September, teens, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems Preferences: September, teens, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular & hidden gems Pace: Medium 35 days in United States BY A USER FROM AUSTRALIA September, teens, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems Preferences: September, teens, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular & hidden gems Pace: Medium 38 days in United States BY A USER FROM AUSTRALIA September, teens, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems Preferences: September, teens, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular & hidden gems Pace: Medium 23 days in United States & Montreal BY A USER FROM ISRAEL October, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems Preferences: October, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular & hidden gems Pace: Medium 11 days in Boston, Tokyo & Kyoto BY A USER FROM UNITED STATES February, culture, outdoors, relaxing, romantic, historic sites, museums, shopping, popular sights Preferences: February, culture, outdoors, relaxing, romantic, historic sites, museums, shopping Attraction style: Popular sights Pace: Medium 20 days in New York City & New England BY A USER FROM BELGIUM July, teens, kids, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife, popular & hidden gems Preferences: July, teens, kids, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife Attraction style: Popular & hidden gems Pace: Medium 8 days in Portland, Bar Harbor & Niagara Falls BY A USER FROM UNITED STATES October, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife, slow & easy, popular & hidden gems Preferences: October, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife Attraction style: Popular & hidden gems Pace: Slow & easy 36 days in United States BY A USER FROM AUSTRALIA June, teens, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems Preferences: June, teens, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular & hidden gems Pace: Medium 13 days in Boston & Ireland BY A USER FROM UNITED STATES October, culture, outdoors, relaxing, beaches, historic sites, hidden gems Preferences: October, culture, outdoors, relaxing, beaches, historic sites Attraction style: Hidden gems Pace: Medium 11 days in Boston, New York City & Washington DC BY A USER FROM ARUBA June, culture, outdoors, relaxing, historic sites, museums, shopping, popular sights Preferences: June, culture, outdoors, relaxing, historic sites, museums, shopping Attraction style: Popular sights Pace: Medium 26 days in New England BY A USER FROM SLOVAKIA July, teens, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife, popular & hidden gems Preferences: July, teens, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife Attraction style: Popular & hidden gems Pace: Medium 31 days in Houston & Boston BY A USER FROM UNITED STATES October, teens, kids, outdoors, relaxing, historic sites, museums, shopping, wildlife, popular & hidden gems Preferences: October, teens, kids, outdoors, relaxing, historic sites, museums, shopping, wildlife Attraction style: Popular & hidden gems Pace: Medium
See more plans