8 days in New England Itinerary

8 days in New England Itinerary

Created using Inspirock New England trip itinerary planner

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

Route & dates

8 days in New England Itinerary

Start: Chicago
Fly:  4​h
1
Boston
— 2 nights
Drive:  2​h 15​min
2
Lincoln
— 1 night
Drive:  1​h 15​min
3
North Conway
— 1 night
Drive:  3​h 15​min
4
Rockland
— 1 night
Drive:  2​h 15​min
5
Bar Harbor, Mount Desert Island
— 2 nights
Fly:  7​h 45​min
End: Chicago

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.
When in Boston, make a side trip to see Marginal Way Walkway in Ogunquit, approximately 1h 30 min away. And it doesn't end there: admire the masterpieces at Museum of Fine Arts, take a stroll through North End, ponder the world of politics at Old State House, and don't miss a visit to Faneuil Hall Marketplace.

To see traveler tips, reviews, other places to visit, and tourist information, you can read our Boston trip site .

Chicago to Boston is an approximately 4-hour flight. You can also do a combination of flight and bus; or drive. You'll lose 1 hour traveling from Chicago to Boston due to the time zone difference. October in Boston sees daily highs of 64°F and lows of 50°F at night. Wrap up your sightseeing on the 18th (Fri) to allow time to drive to Lincoln.

Things to do in Boston

Historic Sites Museums Parks

Side Trip

Marginal Way Walkway
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Marginal Way Walkway ©
Marginal Way Walkway
Boston Public Garden ©
Boston Public Garden

1
night
Lincoln

Lincoln ©
Stretching through the White Mountain National Forest, Lincoln welcomes hikers along the Appalachian Trail.
On the 19th (Sat), admire the majestic nature at Franconia Notch State Park, explore the striking landscape at The Basin at Franconia Notch State Park, and then kick your exploration up a notch at some of the top local zipline courses and adventure parks.

To find photos, maps, more things to do, and tourist information, refer to the Lincoln trip maker .

Getting from Boston to Lincoln by car takes about 2.5 hours. Other options: take a bus. Traveling from Boston in October, Lincoln is little chillier at night with lows of 38°F. Finish your sightseeing early on the 19th (Sat) to allow enough time to drive to North Conway.

Things to do in Lincoln

Nature Parks Adventure

Side Trip

Franconia
Highlights from your plan
The Basin at Franconia Notch State Park ©
Franconia Notch State Park ©
Franconia Notch State Park

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 20th (Sun), look and learn at Mount Washington Observatory Weather Discovery Center, then take in the dramatic natural features at Cathedral Ledge, and then take a memorable drive along Kancamagus Highway.

To find where to stay, photos, reviews, and more tourist information, go to the North Conway trip itinerary planning app .

Drive from Lincoln to North Conway in 1.5 hours. Alternatively, you can take a bus. Traveling from Lincoln in October, plan for a bit warmer nights in North Conway, with lows around 45°F. Cap off your sightseeing on the 20th (Sun) early enough to go by car to Rockland.

Things to do in North Conway

Outdoors Scenic Drive Nature
Highlights from your plan
Kancamagus Highway ©
Kancamagus Highway
Cathedral Ledge ©
Cathedral Ledge

1
night
Rockland

Rockland ©
Rockland is a city in Knox County, Maine, in the United States. On the 21st (Mon), steep yourself in history at Farnsworth Art Museum, then examine the collection at Owls Head Transportation Museum, and then admire the majestic nature at Camden Hills State Park.

To find where to stay, traveler tips, ratings, and more tourist information, use the Rockland trip builder website .

Drive from North Conway to Rockland in 3.5 hours. Alternatively, you can do a combination of car and bus; or take a bus. In October in Rockland, expect temperatures between 58°F during the day and 42°F at night. Finish your sightseeing early on the 21st (Mon) to allow enough time to drive to Bar Harbor.

Things to do in Rockland

Museums Nature Parks

Side Trips

Owls Head Transportation Museum, Camden Hills State Park
Highlights from your plan
Farnsworth Art Museum ©
Farnsworth Art Museum
Camden Hills State Park ©
Camden Hills State Park
Owls Head Transportation Museum ©
Owls Head Transportation Museum

2
nights
Bar Harbor, Mount Desert Island

Bar Harbor ©
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Kick off your visit on the 22nd (Tue): take in the spiritual surroundings of St. Saviour's Church :, tour the pleasant surroundings at Ocean Path, then take in the dramatic natural features at Thunder Hole, and finally kick back and relax at Sand Beach. Keep things going the next day: hike along Champlain Mountain & Beehive Loop Trail and then explore the landscape on two wheels at Carriage Roads.

To find other places to visit, photos, maps, and other tourist information, refer to the Bar Harbor online tour planner .

You can drive from Rockland to Bar Harbor in 2.5 hours. Alternatively, you can take a bus. In October, daytime highs in Bar Harbor are 59°F, while nighttime lows are 42°F. Finish your sightseeing early on the 23rd (Wed) to allow enough time to travel back home.

Things to do in Bar Harbor

Parks Outdoors Trails

Side Trip

Acadia National Park
Highlights from your plan
Thunder Hole ©
Thunder Hole
Carriage Roads ©
Carriage Roads
Champlain Mountain & Beehive Loop Trail ©

Similar Plans

7 days in New England BY A USER FROM UNITED STATES May, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, slow & easy, popular & hidden gems PREFERENCES: May, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Slow & easy 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 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 10 days in New York City & New England BY A USER FROM UNITED STATES October, culture, outdoors, romantic, historic sites, museums, popular & hidden gems PREFERENCES: October, culture, outdoors, romantic, historic sites, museums ATTRACTION STYLE: Popular & hidden gems PACE: Medium 9 days in New England BY A USER FROM ISRAEL November, outdoors, relaxing, shopping, wildlife, popular sights PREFERENCES: November, outdoors, relaxing, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 20 days in New England BY A USER FROM BELGIUM July, teens, kids, culture, outdoors, relaxing, beaches, historic sites, popular sights PREFERENCES: July, teens, kids, culture, outdoors, relaxing, beaches, historic sites 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 9 days in New England BY A USER FROM UNITED STATES October, beaches, historic sites, museums, popular sights PREFERENCES: October, beaches, historic sites, museums ATTRACTION STYLE: Popular sights PACE: Medium 11 days in New England BY A USER FROM IRAQ October, outdoors, historic sites, wildlife, popular sights PREFERENCES: October, outdoors, historic sites, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 7 days in New England BY A USER FROM UNITED STATES May, culture, relaxing, romantic, beaches, historic sites, museums, wildlife, popular & hidden gems PREFERENCES: May, culture, relaxing, romantic, beaches, historic sites, museums, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 13 days in New England BY A USER FROM CANADA September, culture, outdoors, historic sites, wildlife, slow & easy, popular sights PREFERENCES: September, culture, outdoors, historic sites, wildlife ATTRACTION STYLE: Popular sights PACE: Slow & easy 13 days in New England BY A USER FROM SWEDEN October, culture, outdoors, historic sites, museums, hidden gems PREFERENCES: October, culture, outdoors, historic sites, museums ATTRACTION STYLE: Hidden gems PACE: Medium
View more plans