38 days in New England Itinerary

38 days in New England Itinerary

Created using Inspirock New England attractions planner

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Route & dates

38 days in New England Itinerary

Start: New York City
1
New Haven
— 2 nights
train:  1​h 30​min
2
Providence
— 2 nights
Drive:  45​min
3
Newport
— 3 nights
Drive:  1​h 15​min
4
Plymouth
— 2 nights
train:  1​h
5
Boston
— 4 nights
train:  45​min
6
Salem
— 3 nights
Drive:  1​h
7
Portsmouth
— 1 night
Drive:  1​h
8
Portland
— 2 nights
Drive:  3​h 30​min
9
Bar Harbor, Mount Desert Island
— 4 nights
bus:  1​h 15​min
10
Bangor
— 3 nights
Drive:  4​h 15​min
11
Lincoln
— 3 nights
Drive:  1​h 45​min
12
Woodstock
— 2 nights
Drive:  1​h 30​min
13
Manchester
— 3 nights
Drive:  2​h 45​min
14
Burlington
— 3 nights
Fly:  4​h
End: New York City

2
nights
New Haven

New Haven ©
New Haven, in the U.S. On the 30th (Mon), contemplate the long history of The Mark Twain House & Museum, then see the interesting displays at The Submarine Force Museum, and then get lost in a book at Beinecke Rare Book & Manuscript Library. On the 1st (Tue), you'll have a packed day of sightseeing: explore the world behind art at Yale Center for British Art, then admire all the interesting features of Yale University, then get a new perspective on nature at Yale Peabody Museum of Natural History, and finally walk around East Rock Park.

For maps, traveler tips, more things to do, and tourist information, read New Haven trip itinerary maker tool .

New York City to New Haven is an approximately 2-hour car ride. You can also take a train; or take a bus. Traveling from New York City in September, you can expect nighttime temperatures to be slightly colder in New Haven, with lows of 17°C. On the 2nd (Wed), wrap the sightseeing up by early afternoon so you can take a train to Providence.

Things to do in New Haven

Museums Historic Sites Parks

Side Trips

The Submarine Force Museum, The Mark Twain House & Museum
Find places to stay Sep 30 — Oct 2:
Highlights from your plan
Yale University Art Gallery ©
Yale University Art Gallery
The Mark Twain House & Museum ©
The Mark Twain House & Museum

2
nights
Providence

Providence ©
Providence has undergone a major upgrade in recent years, transforming from a rough-around-the-edges industrial city into an epicenter of culture.
Start off your visit on the 2nd (Wed): appreciate the extensive heritage of WaterFire Providence. On the 3rd (Thu), you'll have a packed day of sightseeing: learn about wildlife with up-close encounters at Roger Williams Park Zoo, see the interesting displays at Battleship Cove, then explore the world behind art at RISD Museum, and finally get a sense of history and politics at State House.

For maps, where to stay, traveler tips, and more tourist information, read Providence trip itinerary planning website .

You can take a train from New Haven to Providence in 1.5 hours. Other options are to drive; or take a bus. October in Providence sees daily highs of 22°C and lows of 9°C at night. Cap off your sightseeing on the 4th (Fri) early enough to go by car to Newport.

Things to do in Providence

Museums Historic Sites Parks

Side Trips

Fall River, New Bedford Whaling Museum
Find places to stay Oct 2 — 4:
Highlights from your plan
New Bedford Whaling Museum ©
New Bedford Whaling Museum
Lizzie Borden House ©
Lizzie Borden House
Roger Williams Park Zoo ©
Roger Williams Park Zoo

3
nights
Newport

Newport ©
With coastline on the west, south, and east, Newport is a maritime city with a rich history.
On the 5th (Sat), view the masterpieces at Thames Glass, take a memorable drive along Ocean Drive Historic District, then admire the striking features of Marble House, and finally make a trip to Cliff Walk. On your second day here, admire the landmark architecture of The Elms, see the interesting displays at The Breakers, then pause for some serene contemplation at St. Mary's Catholic Church, and finally observe the fascinating underwater world at Mystic Aquarium.

For maps, more things to do, photos, and more tourist information, read our Newport day trip app .

You can drive from Providence to Newport in an hour. Alternatively, you can take a bus; or ride a ferry. In October, daytime highs in Newport are 20°C, while nighttime lows are 11°C. Finish up your sightseeing early on the 7th (Mon) so you can go by car to Plymouth.

Things to do in Newport

Historic Sites Parks Outdoors

Side Trip

Mystic Aquarium
Find places to stay Oct 4 — 7:
Highlights from your plan
Ocean Drive Historic District ©
Ocean Drive Historic District
The Breakers ©
The Breakers
The Elms ©
The Elms

2
nights
Plymouth

Plymouth ©
Rightly calling itself "America's Hometown," Plymouth holds a prominent place in the nation's history and culture as the site of the first Puritan colony.
Plymouth is known for museums, historic sites, nature, wildlife, and parks. Your plan includes some of its best attractions: get engrossed in the history at Plimoth Plantation, contemplate the waterfront views at Cape Cod Canal, make a trip to Mayflower II, and take in nature's colorful creations at Brewster Gardens.

To find more things to do, other places to visit, traveler tips, and more tourist information, read our Plymouth sightseeing planner.

Traveling by car from Newport to Plymouth takes 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. Expect a daytime high around 21°C in October, and nighttime lows around 9°C. Finish up your sightseeing early on the 9th (Wed) so you can go by car to Boston.

Things to do in Plymouth

Museums Outdoors Parks

Side Trip

Cape Cod Canal
Find places to stay Oct 7 — 9:
Highlights from your plan
Plimoth Plantation ©
Plimoth Plantation
Plymouth Rock ©
Plymouth Rock
Jenney Museum ©
Jenney Museum

4
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.
Boston is known for historic sites, museums, parks, shopping, and nightlife. Your plan includes some of its best attractions: admire all the interesting features of Fenway Park, make a trip to Boston Public Library, buy something for everyone on your list at Faneuil Hall Marketplace, and get curious at Museum of Science.

For where to stay, maps, reviews, and other tourist information, read Boston planner .

You can drive from Plymouth to Boston in an hour. Other options are to take a bus; or take a train. In October, daytime highs in Boston are 20°C, while nighttime lows are 11°C. Wrap up your sightseeing by early afternoon on the 13th (Sun) to allow enough time to take a train to Salem.

Things to do in Boston

Museums Historic Sites Parks

Side Trips

Mount Auburn Cemetery, Cutler Park
Find places to stay Oct 9 — 13:
Highlights from your plan
Freedom Trail ©
Freedom Trail
Fenway Park ©
Fenway Park
Museum of Fine Arts ©
Museum of Fine Arts

3
nights
Salem

Salem ©
Best known for its 1692 witch trials, Salem has a number of significant historical sites, a bustling downtown, and many witch-themed attractions.
On the 13th (Sun), don't miss a visit to Stickworks Statue - What the Birds Know - by Patrick Dougherty and then pause for some photo ops at Bewitched Statue of Elizabeth Montgomery. Get ready for a full day of sightseeing on the next day: take an in-depth tour of Witch House, then walk around Salem Witch Trials Memorial, then stroll the grounds of Old Burying Point Cemetery, and finally explore the world behind art at Count Orlok's Nightmare Gallery.

To find photos, maps, where to stay, and tourist information, read Salem day trip website .

You can take a train from Boston to Salem in an hour. Alternatively, you can drive; or take a bus. Traveling from Boston in October, plan for a bit cooler nights in Salem, with lows around 8°C. Wrap up your sightseeing on the 16th (Wed) early enough to drive to Portsmouth.

Things to do in Salem

Museums Historic Sites Parks
Find places to stay Oct 13 — 16:
Highlights from your plan
Peabody Essex Museum ©
Peabody Essex Museum
The House of the Seven Gables ©
The House of the Seven Gables
Salem Witch Museum ©
Salem Witch Museum

1
night
Portsmouth

Portsmouth ©
Portsmouth is a city in Rockingham County, New Hampshire, in the United States. On the 16th (Wed), examine the collection at USS Albacore Museum, make a trip to Market Square, then contemplate the long history of Strawbery Banke Museum, and finally take in nature's colorful creations at Prescott Park. On the next day, look for gifts at The Salt Cellar, then explore the striking landscape at Perkins Cove, then appreciate the extensive heritage of Marginal Way Walkway, and finally enjoy the sand and surf at Ogunquit Beach.

For other places to visit, where to stay, photos, and other tourist information, you can read our Portsmouth vacation planner .

Drive from Salem to Portsmouth in an hour. Alternatively, you can do a combination of train and bus; or take a bus. In October, daily temperatures in Portsmouth can reach 19°C, while at night they dip to 7°C. Wrap up your sightseeing on the 17th (Thu) to allow time to drive to Portland.

Things to do in Portsmouth

Parks Museums Historic Sites

Side Trip

Ogunquit
Find places to stay Oct 16 — 17:
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Ogunquit Beach ©
Ogunquit Beach
Perkins Cove ©
Perkins Cove

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 18th (Fri), take a stroll through Old Port, explore the world behind art at Portland Museum of Art, then get engrossed in the history at Victoria Mansion, and finally sample the tasty concoctions at Allagash Brewery. On the 19th (Sat), you'll have a packed day of sightseeing: stroll through Old Orchard Beach, then indulge your thirst for a good beer at Rising Tide Brewing Company, then examine the collection at Portland Head Light, and finally don't miss a visit to Commercial Street.

For other places to visit, ratings, and more tourist information, read Portland day trip tool .

Drive from Portsmouth to Portland in an hour. Alternatively, you can take a train. Expect a daytime high around 19°C in October, and nighttime lows around 7°C. Finish your sightseeing early on the 19th (Sat) so you can drive to Bar Harbor.

Things to do in Portland

Museums Parks Outdoors

Side Trips

Old Orchard Beach, Portland Head Light
Find places to stay Oct 17 — 19:
Highlights from your plan
Portland Museum of Art ©
Portland Museum of Art
Portland Head Light ©
Portland Head Light
Old Port ©
Old Port

4
nights
Bar Harbor, Mount Desert Island

Bar Harbor ©
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Spend the 20th (Sun) exploring nature at Acadia National Park. And it doesn't end there: step off the mainland to explore Mount Desert Island, take a memorable drive along Park Loop Road, hike along Ocean Path, and get interesting insight from Tours.

Plan a trip to Bar Harbor easily and quickly by telling Inspirock to suggest an itinerary.

Drive from Portland to Bar Harbor in 3.5 hours. Alternatively, you can take a bus; or do a combination of bus and flight. In October in Bar Harbor, expect temperatures between 17°C during the day and 6°C at night. Finish up your sightseeing early on the 23rd (Wed) so you can go by car to Bangor.

Things to do in Bar Harbor

Parks Nature Outdoors

Side Trip

Acadia National Park
Find places to stay Oct 19 — 23:
Highlights from your plan
Acadia National Park ©
Acadia National Park
Cadillac Mountain ©
Cadillac Mountain
Shore Path ©
Shore Path

3
nights
Bangor

Bangor ©
Bangor is a city along the Penobscot River in the U.S. On the 24th (Thu), try your luck at Hollywood Casino, then pause for some photo ops at Paul Bunyan Statue, then examine the collection at Cole Land Transportation Museum, and finally explore the landscape on two wheels at Penobscot River Walkway. Keep things going the next day: browse the exhibits of Farnsworth Art Museum, take in the awesome beauty at Mount Battie, and then admire the striking features of Stephen King's House.

For photos, ratings, traveler tips, and more tourist information, you can read our Bangor vacation planning tool .

You can drive from Bar Harbor to Bangor in 1.5 hours. Alternatively, you can take a bus; or take a shuttle. In October in Bangor, expect temperatures between 19°C during the day and 5°C at night. Wrap up your sightseeing by early afternoon on the 26th (Sat) to allow time for the car ride to Lincoln.

Things to do in Bangor

Parks Museums Nature

Side Trips

Mount Battie, Farnsworth Art Museum
Find places to stay Oct 23 — 26:
Highlights from your plan
Mount Battie ©
Mount Battie
Mount Hope Garden Cemetery ©
Mount Hope Garden Cemetery
Farnsworth Art Museum ©
Farnsworth Art Museum

3
nights
Lincoln

Stretching through the White Mountain National Forest, Lincoln welcomes hikers along the Appalachian Trail.
Explore Lincoln's surroundings by going to North Conway (Diana's Baths & Kancamagus Highway). Next up on the itinerary: get interesting insight from Tours, take in the dramatic natural features at The Basin at Franconia Notch State Park, make a trip to Loon Mountain Ministries, and admire the sheer force of Flume Gorge.

For ratings, maps, photos, and other tourist information, read Lincoln trip itinerary planner .

Getting from Bangor to Lincoln by car takes about 4.5 hours. Other options: do a combination of bus and flight; or take a bus. Expect a daytime high around 18°C in October, and nighttime lows around 3°C. On the 29th (Tue), wrap the sightseeing up by early afternoon so you can drive to Woodstock.

Things to do in Lincoln

Outdoors Parks Nature

Side Trips

North Conway, Flume Gorge
Find places to stay Oct 26 — 29:
Highlights from your plan
Zipline
Kancamagus Highway ©
Kancamagus Highway
Flume Gorge ©
Flume Gorge

2
nights
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. Start off your visit on the 29th (Tue): appreciate the history behind Saint-Gaudens National Historic Site. On the 30th (Wed), you'll have a packed day of sightseeing: steep yourself in history at Billings Farm & Museum, admire all the interesting features of Sugarbush Farm, and then explore the stunning scenery at Quechee Gorge.

To find maps, traveler tips, more things to do, and tourist information, refer to the Woodstock day trip planning site .

Drive from Lincoln to Woodstock in 2 hours. Alternatively, you can take a bus. In October, daytime highs in Woodstock are 19°C, while nighttime lows are 5°C. Wrap up your sightseeing on the 31st (Thu) to allow time to drive to Manchester.

Things to do in Woodstock

Historic Sites Parks Nature

Side Trips

Saint-Gaudens National Historic Site, Quechee Gorge
Find places to stay Oct 29 — 31:
Highlights from your plan
Billings Farm & Museum ©
Billings Farm & Museum
Sugarbush Farm ©
Sugarbush Farm

3
nights
Manchester

Manchester ©
Manchester is a town in, and one of two shire towns (county seats) of, Bennington County, Vermont, United States. Kick off your visit on the 1st (Fri): take your sightseeing to a higher altitude at Equinox Mountain, then take in the exciting artwork at Southern Vermont Arts Center, then admire the natural beauty at Hildene, The Lincoln Family Home, and finally look for gifts at Northshire Bookstore. Get ready for a full day of sightseeing on the 2nd (Sat): look for all kinds of wild species at Equinox Preservation Trust, admire the sheer force of Lye Brook Falls, then explore and take pictures at North Meadow Farm, and finally revel in the low prices at Manchester Designer Outlets.

For reviews, other places to visit, ratings, and other tourist information, read our Manchester tour site .

You can drive from Woodstock to Manchester in 1.5 hours. Another option is to take a bus. In October, daily temperatures in Manchester can reach 19°C, while at night they dip to 5°C. Finish your sightseeing early on the 3rd (Sun) to allow enough time to drive to Burlington.

Things to do in Manchester

Parks Nature Shopping

Side Trip

Equinox Mountain
Find places to stay Oct 31 — Nov 3:
Highlights from your plan
Hildene, The Lincoln Family Home ©
North Meadow Farm ©
North Meadow Farm
Northshire Bookstore ©
Northshire Bookstore

3
nights
Burlington

Burlington ©
Burlington is the most populous city in the U.S. When in Burlington, make a side trip to see Fort Ticonderoga in Ticonderoga, approximately 1h 15 min away. There's still lots to do: hike along Burlington Bike Path, savor the flavors at Food & Drink, contemplate the long history of Shelburne Farms, and admire all the interesting features of University of Vermont.

For reviews, photos, and more tourist information, read Burlington holiday planner.

Drive from Manchester to Burlington in 3 hours. Alternatively, you can take a bus. In November in Burlington, expect temperatures between 9°C during the day and 0°C at night. Wrap up your sightseeing by early afternoon on the 6th (Wed) to allow enough time to travel back home.

Things to do in Burlington

Museums Parks Historic Sites

Side Trips

Shelburne, Fort Ticonderoga
Find places to stay Nov 3 — 6:
Highlights from your plan
ECHO, Leahy Center for Lake Champlain ©
Burlington Bike Path ©
Burlington Bike Path
Shelburne Museum ©
Shelburne Museum

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