14 days in New England Itinerary

14 days in New England Itinerary

Created using Inspirock United States trip itinerary planner

Make it your trip
Fly
1
Boston
— 2 nights
Fly
2
Nantucket
— 1 night
Ferry to Oak Bluffs, Martha's Vineyard, MA, Bus to Edgartown
3
Edgartown
— 1 night
Ferry to New Bedford, MA, Taxi to Newport
4
Newport
— 2 nights
Drive
5
Manchester
— 1 night
Drive
6
Bretton Woods
— 1 night
Drive
7
Bar Harbor, Mount Desert Island
— 2 nights
Drive
8
Portland
— 2 nights
Fly

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Boston

— 2 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.
Boston is known for historic sites, museums, and parks. Your trip includes some of its best attractions: admire the natural beauty at Boston Public Garden, take an in-depth tour of Boston Tea Party Ships & Museum, take a tour by water with Boat Tours & Water Sports, and get to know the fascinating history of Freedom Trail.

To find reviews, more things to do, maps, and other tourist information, go to the Boston holiday maker.

Knoxville to Boston is an approximately 4-hour flight. You can also drive; or take a bus. Expect slightly colder weather when traveling from Knoxville in October: highs in Boston hover around 64°F, while lows dip to 50°F. Finish your sightseeing early on the 3rd (Mon) to allow enough time to fly to Nantucket.

Things to do in Boston

Museums · Historic Sites · Parks · Neighborhoods

Nantucket

— 1 night
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Kick off your visit on the 4th (Tue): see the interesting displays at Whaling Museum, then don't miss a visit to Brant Point Lighthouse, and then enjoy the sea views from Sankaty Head Lighthouse.

Inspirock's itinerary builder makes planning a Nantucket trip simple and quick.

Fly from Boston to Nantucket in 2.5 hours. Alternatively, you can do a combination of car and ferry; or do a combination of bus and ferry. In October, plan for daily highs up to 64°F, and evening lows to 51°F. Finish your sightseeing early on the 4th (Tue) to allow enough time to travel to Edgartown.

Things to do in Nantucket

Historic Sites · Museums

Edgartown

— 1 night
Edgartown is a town located on Martha's Vineyard in Dukes County, Massachusetts, United States. Kick off your visit on the 5th (Wed): admire the natural beauty at Mytoi, then admire the landmark architecture of Trinity Park Tabernacle, then don't miss a visit to Flying Horses Carousel, and finally visit Martha's Vineyard Camp meeting Association (MVCMA).

For other places to visit, traveler tips, and more tourist information, refer to the Edgartown road trip planning app.

You can do a combination of ferry and bus from Nantucket to Edgartown in 2.5 hours. Expect little chillier evenings in Edgartown when traveling from Nantucket in October, with lows around 46°F. Finish your sightseeing early on the 6th (Thu) so you can travel to Newport.

Things to do in Edgartown

Historic Sites · Neighborhoods · Parks

Side Trip

Newport

— 2 nights

City by the Sea

With coastline on the west, south, and east, Newport is a maritime city with a rich history.
On the 6th (Thu), see what you can catch with Fish'n Tales Adventures, examine the collection at The Breakers, and then tour the pleasant surroundings at Cliff Walk. On the 7th (Fri), you'll have a packed day of sightseeing: tour in style with a train tour, then explore and take pictures at Ocean Drive Historic District, and then stroll around Fort Adams State Park.

For where to stay, photos, ratings, and tourist information, you can read our Newport trip itinerary builder website.

Traveling by combination of ferry and taxi from Edgartown to Newport takes 2.5 hours. Alternatively, you can do a combination of car and ferry; or do a combination of bus and ferry. In October in Newport, expect temperatures between 64°F during the day and 50°F at night. Finish your sightseeing early on the 8th (Sat) to allow enough time to drive to Manchester.

Things to do in Newport

Historic Sites · Outdoors · Parks · Tours

Manchester

— 1 night
Manchester is the largest city in the U.S. state of New Hampshire, the eleventh largest city in New England, and as of 2016 the largest city in northern New England, an area comprising the states of Maine, New Hampshire, and Vermont. Start off your visit on the 8th (Sat): explore the world behind art at Currier Museum of Art, then experience rural life at Charmingfare Farm, and then learn about winemaking at Moonlight Meadery & Hidden Moon Brewing.

To find other places to visit, ratings, traveler tips, and other tourist information, read Manchester travel route tool.

Drive from Newport to Manchester in 2.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. Traveling from Newport in October, plan for a bit cooler nights in Manchester, with lows around 45°F. Wrap up your sightseeing on the 9th (Sun) early enough to drive to Bretton Woods.

Things to do in Manchester

Museums · Wineries

Side Trips

Bretton Woods

— 1 night
Bretton Woods is an area within the town of Carroll, New Hampshire, United States, whose principal points of interest are three leisure and recreation facilities. On the 9th (Sun), immerse yourself in nature at Franconia Notch State Park and then surround yourself with nature on Bretton Woods Canopy Tour.

To find maps, ratings, where to stay, and tourist information, go to the Bretton Woods itinerary website.

You can drive from Manchester to Bretton Woods in 2 hours. Alternatively, you can do a combination of bus and taxi; or do a combination of bus and taxi. Traveling from Manchester in October, expect nights in Bretton Woods to be a bit cooler, around 29°F, while days are colder, around 39°F. Cap off your sightseeing on the 10th (Mon) early enough to go by car to Bar Harbor.

Things to do in Bretton Woods

Wildlife · Tours · Outdoors · Parks

Side Trip

Bar Harbor, Mount Desert Island

— 2 nights
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Start off your visit on the 10th (Mon): trek along Ocean Path and then contemplate the waterfront views at Jordan Pond Path Trailhead. On the next day, take a memorable drive along Park Loop Road, then take in the awesome beauty at Cadillac Mountain, and then look for gifts at Bar Harbor Popcorn.

Inspirock's itinerary builder makes planning a Bar Harbor trip simple and quick.

Traveling by car from Bretton Woods to Bar Harbor takes 5.5 hours. Alternatively, you can fly; or take a bus. Traveling from Bretton Woods in October, things will get a bit warmer in Bar Harbor: highs are around 59°F and lows about 42°F. Wrap up your sightseeing on the 12th (Wed) to allow time to drive to Portland.

Things to do in Bar Harbor

Parks · Outdoors · Nature · Shopping

Side Trip

Portland

— 2 nights

The Forest City

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.
Portland is known for breweries & distilleries, museums, and nightlife. Your trip includes some of its best attractions: enjoy the sea views from Portland Head Light, take a stroll through Old Port, sample the tasty concoctions at Allagash Brewing Company, and learn the secrets of beer at a beer tour and tasting.

To see ratings, other places to visit, traveler tips, and other tourist information, read our Portland trip itinerary planner.

Traveling by car from Bar Harbor to Portland takes 3.5 hours. Alternatively, you can do a combination of flight and bus; or take a bus. October in Portland sees daily highs of 62°F and lows of 43°F at night. Wrap up your sightseeing by early afternoon on the 14th (Fri) to allow time for the flight back home.

Things to do in Portland

Breweries & Distilleries · Tours · Historic Sites · Museums

Side Trip

Martha's Vineyard travel guide

4.3
Beaches · Lighthouses · Landmarks
Martha's Vineyard is an island located south of Cape Cod in Massachusetts that is known for being an affluent summer colony. It includes the smaller Chappaquiddick Island which is usually connected to the Vineyard, though storms and hurricanes have been known to separate the two. The last such separation of the islands was in 2007 and the two islands are again connected as of April 2, 2015.It is the 58th largest island in the United States, with a land area of 100sqmi, and the third largest on the East Coast of the United States, after Long Island and Mount Desert Island. The island constitutes the bulk of Dukes County, Massachusetts, which also includes the Elizabeth Islands and the island of Nomans Land.The Vineyard was home to one of the earliest known deaf communities in the United States; consequently, a special sign language developed on the island called Martha's Vineyard Sign Language (MVSL).The 2010 census reported a year-round population of 16,535 residents, although the summer population can swell to more than 100,000 people. About 56% of the Vineyard's 14,621 homes are seasonally occupied.

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