17 days in New England Itinerary

17 days in New England Itinerary

Created using Inspirock New England trip planner

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Plan created by another user. Make it yours
Drive
1
Newport
— 3 nights
Drive to Ocean Street Terminal, Hyannis, MA, Ferry to Nantucket
2
Nantucket
— 1 night
Fly
3
Bar Harbor, Mount Desert Island
— 3 nights
Drive
4
Rockland
— 2 nights
Drive
5
Kennebunkport
— 2 nights
Drive
6
Stowe
— 1 night
Drive
7
Pittsfield
— 3 nights
Drive

S M T W T F S
20
21
22
23
24
25
26
27
28
29
30
1
2
3
4
5
6
7
8
9
10

3
nights
Newport

City by the Sea

With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Your inner history buff will appreciate Rough Point Museum and The Preservation Society of Newport County. You'll explore the less-touristy side of things at Fish'n Tales Adventures and Trinity Church. Step out of Newport to go to Bristol and see Blithewold Mansion, Gardens & Arboretum, which is approximately 32 minutes away. There's lots more to do: admire the majestic nature at Brenton Point State Park, cruise along Bellevue Avenue Historic District, enjoy the sea views from Beavertail Lighthouse and Park, and steep yourself in history at Chateau-sur-Mer.

To find maps, more things to do, photos, and tourist information, refer to the Newport driving holiday planner.

Madison to Newport is an approximately 7.5-hour flight. You can also drive; or do a combination of bus and subway. Traveling from Madison to Newport, you'll lose 1 hour due to the time zone difference. In September, daytime highs in Newport are 74°F, while nighttime lows are 58°F. Wrap up your sightseeing on the 26th (Sat) to allow time to travel to Nantucket.

Things to do in Newport

Historic Sites · Parks · Nature · Outdoors

Side Trips

1
night
Nantucket

Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Start off your visit on the 27th (Sun): take in the architecture and atmosphere at Nantucket United Methodist Church, contemplate the long history of Quaker Meeting House, then pause for some serene contemplation at St Paul's Episcopal Church, and finally kick back and relax at Nobadeer.

For photos, more things to do, where to stay, and more tourist information, read our Nantucket road trip planning app.

You can do a combination of car and ferry from Newport to Nantucket in 3.5 hours. Other options are to do a combination of taxi and ferry; or do a combination of taxi and flight. In September in Nantucket, expect temperatures between 71°F during the day and 59°F at night. Finish your sightseeing early on the 27th (Sun) so you can travel to Bar Harbor.

Things to do in Nantucket

Historic Sites · Parks · Outdoors · Beaches

3
nights
Bar Harbor, Mount Desert Island

Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Popular historic sites such as St. Saviour's Church : and Egg Rock Light are in your itinerary. Take a break from the city and head to Precipice Trail and Eagle Lake Acadia National Park. There's still lots to do: trek along Cadillac Mountain North Ridge Trail, stroll through Bar Island Trails, head outdoors with Dorr Mountain, and walk around Agamont Park.

To see reviews, ratings, and tourist information, read our Bar Harbor trip itinerary builder app.

Traveling by flight from Nantucket to Bar Harbor takes 6 hours. Alternatively, you can do a combination of ferry and car; or do a combination of ferry and bus. Traveling from Nantucket in September, you can expect nighttime temperatures to be little chillier in Bar Harbor, with lows of 52°F. Finish your sightseeing early on the 30th (Wed) to allow enough time to drive to Rockland.

Things to do in Bar Harbor

Parks · Outdoors · Trails · Nature

Side Trips

2
nights
Rockland

Rockland is a city in Knox County, Maine, in the United States. Kick off your visit on the 1st (Thu): admire the majestic nature at Owl's Head State Park, then examine the collection at Sail Power and Steam Museum, then visit a coastal fixture at Maine Lighthouse Museum, and finally look for gifts at Fiore Artisan Olive Oils and Vinegars. Get ready for a full day of sightseeing on the 2nd (Fri): walk around Camden Harbor Park and Amphitheatre, don't miss a visit to Curtis Island Light, then contemplate the long history of High Street Historic District, and finally walk around Harbor Park.

For maps, traveler tips, where to stay, and tourist information, you can read our Rockland day trip planning website.

Traveling by car from Bar Harbor to Rockland takes 2.5 hours. Alternatively, you can drive; or take a bus. Expect a daytime high around 69°F in September, and nighttime lows around 51°F. Wrap up your sightseeing on the 2nd (Fri) early enough to drive to Kennebunkport.

Things to do in Rockland

Parks · Museums · Historic Sites · Neighborhoods

Side Trips

2
nights
Kennebunkport

Kennebunkport is a town in York County, Maine, United States. On the 3rd (Sat), view the masterpieces at Compliments, relax and rejuvenate at Cottage Breeze Day Spa & Boutique, then get outside with Fisherman's Walk, then visit a coastal fixture at Portsmouth Harbor Lighthouse, and finally admire the majestic nature at Odiorne Point State Park. Keep things going the next day: see what you can catch with a fishing tour, stop by Maine-ly Drizzle, then get to know the fascinating history of Parson's Way, and finally make a trip to President Bush Compound.

To find more things to do, where to stay, ratings, and more tourist information, read our Kennebunkport trip itinerary builder website.

Traveling by car from Rockland to Kennebunkport takes 2.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. In October in Kennebunkport, expect temperatures between 62°F during the day and 38°F at night. Wrap up your sightseeing on the 4th (Sun) early enough to drive to Stowe.

Things to do in Kennebunkport

Historic Sites · Shopping · Outdoors · Wildlife

Side Trips

1
night
Stowe

The Ski Capital of the East

Stowe bustles in winter when skiers and snowboarders flock here to challenge themselves on the long, steep trails careening down Vermont's tallest peak, Mt.
Kick off your visit on the 5th (Mon): take a peaceful walk through Cady Hill Forest, take in the architecture and atmosphere at Blessed Sacrament Church, then relax in the rural setting at Nebraska Knoll Sugar Farm, and finally delve into the lush surroundings at Wiessner Woods.

For maps, where to stay, ratings, and more tourist information, you can read our Stowe trip planner.

Getting from Kennebunkport to Stowe by car takes about 4 hours. Other options: drive; or take a bus; or do a combination of bus and train. In October, daily temperatures in Stowe can reach 60°F, while at night they dip to 39°F. Wrap up your sightseeing on the 5th (Mon) to allow time to travel to Pittsfield.

Things to do in Stowe

Parks · Nature · Historic Sites · Shopping

3
nights
Pittsfield

Pittsfield is the largest city and the county seat of Berkshire County, Massachusetts, United States. Visiting Mohawk Trail State Forest and Pittsfield State Forest will get you outdoors. You'll explore the less-touristy side of things at Savoy Mountain State Forest and Bartlett's Orchard. Go for a jaunt from Pittsfield to Savoy to see Tannery Falls about 38 minutes away. And it doesn't end there: take in the awesome beauty at Lenox Mountain, stroll around Canoe Meadows Wildlife Sanctuary, take an in-depth tour of Herman Melville Memorial Room, and cruise along Concepts of Art Lenox Judaica.

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

Getting from Stowe to Pittsfield by car takes about 4 hours. Expect a daytime high around 60°F in October, and nighttime lows around 40°F. Finish up your sightseeing early on the 8th (Thu) so you can travel back home.

Things to do in Pittsfield

Parks · Nature · Museums · Scenic Drive

Side Trips