8 days in New England Itinerary

8 days in New England Itinerary

Created using Inspirock New England travel planner

Make it your trip
Fly
1
Newport
— 1 night
Fly
2
Bar Harbor, Mount Desert Island
— 1 night
Drive
3
North Conway
— 1 night
Drive
4
Ogunquit
— 1 night
Drive
5
Boston
— 3 nights
Fly

S M T W T F S
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Newport

— 1 night

City by the Sea

With coastline on the west, south, and east, Newport is a maritime city with a rich history.
On the 12th (Tue), admire all the interesting features of Ocean Drive Historic District and then get to know the fascinating history of Cliff Walk. Here are some ideas for day two: examine the collection at The Breakers and then experience rural life at Stone Bridge Farm.

To see more things to do, traveler tips, photos, and more tourist information, read our Newport trip itinerary planning website.

Richmond to Newport is an approximately 3.5-hour flight. You can also drive; or take a bus. While traveling from Richmond, expect little chillier days and about the same nights in Newport, ranging from highs of 64°F to lows of 50°F. Wrap up your sightseeing on the 13th (Wed) early enough to fly to Bar Harbor.

Things to do in Newport

Outdoors · Historic Sites · Parks · Museums

Side Trip

Bar Harbor, Mount Desert Island

— 1 night
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Start off your visit on the 14th (Thu): take a tour by water with Boat Tours & Water Sports and then take in the awesome beauty at Cadillac Mountain.

For photos, other places to visit, where to stay, and more tourist information, use the Bar Harbor road trip planner.

Getting from Newport to Bar Harbor by flight takes about 3 hours. Other options: drive; or take a bus. Plan for little chillier temperatures traveling from Newport in October, with highs in Bar Harbor at 59°F and lows at 42°F. Wrap up your sightseeing on the 14th (Thu) early enough to drive to North Conway.

Things to do in Bar Harbor

Parks · Nature · Tours · Outdoors

Side Trip

North Conway

— 1 night
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 15th (Fri), take in the dramatic scenery at Diana's Baths and then admire all the interesting features of Kancamagus Highway.

To find more things to do, photos, other places to visit, and tourist information, read North Conway trip itinerary planner.

You can drive from Bar Harbor to North Conway in 4.5 hours. Other options are to do a combination of bus and car; or do a combination of flight and bus. In October, plan for daily highs up to 62°F, and evening lows to 45°F. Wrap up your sightseeing on the 15th (Fri) to allow time to drive to Ogunquit.

Things to do in North Conway

Parks · Nature · Outdoors · Scenic Drive

Ogunquit

— 1 night
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.
Kick off your visit on the 16th (Sat): enjoy the sea views from Nubble Lighthouse and then appreciate the extensive heritage of Marginal Way Walkway.

Plan a Ogunquit trip in moments using our itinerary builder.

Traveling by car from North Conway to Ogunquit takes 2 hours. Alternatively, you can take a bus. Traveling from North Conway in October, expect slightly colder with lows of 38°F in Ogunquit. Cap off your sightseeing on the 16th (Sat) early enough to go by car to Boston.

Things to do in Ogunquit

Historic Sites

Side Trip

Boston

— 3 nights

Beantown

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.
Change things up with these side-trips from Boston: Salem (Salem Witch Museum & The House of the Seven Gables). There's still lots to do: admire the natural beauty at Boston Public Garden, get engrossed in the history at USS Constitution Museum, enjoy breathtaking views from Skywalk Observatory, and explore the different monuments and memorials at Granary Burying Ground.

For ratings, maps, where to stay, and tourist information, read Boston trip itinerary builder tool.

Traveling by car from Ogunquit to Boston takes 1.5 hours. Alternatively, you can do a combination of taxi and train; or take a bus. Plan for somewhat warmer nights when traveling from Ogunquit in October since evenings lows in Boston dip to 50°F. Finish up your sightseeing early on the 19th (Tue) so you can catch the flight back home.

Things to do in Boston

Museums · Historic Sites · Parks · Neighborhoods

Side Trip