The following is a summary of a trip to see the Fall colours between New York City and Stowe, then returning to New York City via Boston, Plymouth, Martha’s Vineyard, Newport (Rhode Island) and the Hamptons. We recommend a much slower pace to take in all there is to see – and perhaps leave out Bridport and Montreal to concentrate on New England.

Our overnight stops were NYC at the beginning of the trip then Hancock, Stowe, Bridport, Montreal, North Conway, Boston, Edgartown, Newport, Montauk and NYC at the end of the trip.

Photos of New England Fall – October 2016 

Photos of Boston to New York City – October/November 2016

Our Itinerary

Fly Qantas from Sydney via LA to JFK NYC. Hire car at JFK NYC. Begin driving tour taking in Hancock – Stowe – Burlington – Montreal – North Conway – Boston – Plymouth – Edgartown (Martha’s Vineyard) – Newport (Rhode Island) – Montauk & Hamptons – NYC. Fly Qantas back to Sydney.

JFK Airport
On arrival at JFK airport in New York City, we overnighted at the Holiday Inn Express NYC JFK Airport. We found that generally the hotels close to JFK Airport were quite expensive and the Holiday Inn Express offered good value for money. It was just an overnight stop as the next morning we wanted to pick up a hire car to begin our ‘leaf peeping’ trip of New England.

Hertz Hire Car
We took the Holiday Inn Express shuttle bus to Federation Circle Station where the Hertz Hire Car office was located (shuttle was free). We collected our car – a medium sized Chevrolet which provided plenty of room for our luggage and good power for the open roads.

Drive NYC to Hancock
Our first night’s accommodation was near Hancock – just over a 3-hour drive from JFK Airport. However there is much to see on the way, so we set off early in the morning.


  • Pretty little village worth a stop and stroll around
  • Good lunch stop is Otto’s Market – old fashioned store and cafe


  • Very attractive town with interesting shops, cafes, attractive buildings.
  • Worth a stop (alternative lunch stop to Germantown).

Great Barrington

  • Attractive town




We spent two nights at the Vacation Village in the Berkshires and highlights in the Hancock area were:


  • Village Bike Rentals: Ride the Ashuwillticook Rail Trail
  • Whitney’s Farm – so many pumpkins for Halloween!

North Adams

  • Dinner – The Public Eat+Drink
  • Mass MoCA if time

Mt Greylock

  • Very pretty drive up to Mt Greylock – autumn colours and views


  • Clark Art Institute

Drive Hancock to Stowe
This is a very pretty drive. We picked up a driving itinerary (from Reception at Vacation Village) to see the covered bridges – highly recommended. Manchester and Dorset were two of the prettiest towns we visited. There is excellent shopping in Manchester.


  • 5 (covered) bridges drive
  • Manchester – lovely town, shopping – recommend staying here
  • Dorset for lunch – beautiful little town
  • Route 30 – scenic route

We stayed two nights in Stowe. This is a beautiful area.

  • The peak of the autumn colours
  • Toll Road to Mount Mansfield (views, snow covered pine trees)
  • Von Trapp family lodge for lunch
  • Drive to Smugglers Notch – beautiful autumn foliage
  • Cable car ride up through the foliage
  • Accommodation: Stowe Motel & Snowdrift

Drive Stowe to Burlington
Driving from Stowe to Burlington was a bit out of our way, however we had read great things about Burlington. We spent one night in Burlington before driving to Montreal. 


Drive Burlington to Montreal
We spent one night in Montreal. Our accommodation was in walking distance from the Old Town which is very special. The cobbled streets and historic buildings are very attractive and there are some great restaurants and shops.


Drive Montreal to North Conway
This drive takes in:

  • Littletown – attractive town where author of Pollyanna lived
  • Mount Washington Resort – viewpoint of Mount Washington
  • Crawford Notch (pretty drive)

North Conway
We spent two nights in North Conway. There is a lot to see and do in this beautiful area and we would recommend a longer stay. The Kancamagus Highway circular drive takes all day, which leaves too little time to appreciate the other sites.

  • Circular drive on Kancamagus Highway for foliage (White Mountain National Forest) and back to North Conway
  • Flume Gorge & Visitor Centre
  • Cannon Mountain Aerial Tramway
  • Mount Washington Resort & Crawford Notch
  • Conway Scenic Railway
  • Settlers Green – outlet shopping
  • Dinner at Chef’s Bistro (
  • Accommodation: Spruce Moose Lodge

Drive North Conway to Boston
This was another beautiful drive through autumn foliage and had us wishing we had more time to spend in the area. The drive passes through pretty villages including Tamworth and Center Sandwich.

We had just two nights in Boston – again not nearly enough time.
Accommodation was generally expensive in Boston however we found a very good Air BnB apartment in a good location (the South End District).

Boston is a city that is easy to walk around – especially the Freedom Trail, Beacon Hill and Little Italy.

Highlights of Boston include:

  • Old Town Trolley Tour
  • Beacon Hill – upmarket historic residential/shopping district
  • Tutte Bakery, Beacon Hill for morning tea
  • Walk the Freedom Trail
  • Holocaust Memorial
  • Kennedy Museums
  • Little Italy for lunch
  • Harvard University (via train)
  • Accommodation: Apartment 6, 534 Tremont Street, South End District of Boston

Side Trip to Iceland
We did a ‘side trip’ to Iceland from Boston! There was a very good airfare from Boston to Reyjavik that we took advantage of – and spent 10 days touring Iceland. On our return to Boston we overnighted at the Four Points by Sheraton at Logan Airport before setting off on the second half of our US trip – to Martha’s Vineyard, Newport Rhode Island, the Hamptons and New York City.

We rented a wonderful touring vehicle from Alamo Car Hire at Logan Airport – a Chrysler Town & Country. When renting a car at Logan Airport, all the hire car companies are in one location – a purpose-built building – Rental Car Centre (RCC). It is very efficient.

Drive Boston to Edgartown (Martha’s Vineyard) via Plymouth
On our way to Edgartown, we spent a few hours in Plymouth – it is well worth a visit and a good place to have lunch. There is much to see and, if interested in American history, it would be worth staying overnight.


  • Mayflower II
  • Pilgrim Hall Museum
  • Church of the Pilgrimage
  • First Parish Church
  • Blue Blinds Bakery – Jewish Bakery – highly recommended (7 North St)
  • KKaties’s Burger Bar delicious burgers (38 Main St. Extension,)
  • Excellent Visitors Information Centre in Plymouth

Before leaving Plymouth, it is a good idea to check the departure time of the car/passenger ferry between Wood Hole and Vineyard Haven (Martha’s Vineyard). We caught the 6.15pm ferry – a large, comfortable vessel with an upstairs passenger seating area that included a buffet bar to buy food and drinks. The ferry trip takes about 45 minutes.

Once off the ferry, it is about a 20 minute drive to Edgartown.

Edgartown, Martha’s Vineyard
Edgartown is an exceptionally beautiful town. We spent 3 nights there and it was a perfect base from which to explore the island of Martha’s Vineyard.

Highlights of Edgartown & Martha’s Vineyard:

  • Edgartown – pretty location, beautiful architecture, restaurants and shops
  • Cycle around Edgartown
  • ‘Behind the Bookstore’ café for lunch recommended
  • Edgartown Books – worth a visit
  • Drive around island – highlights: Edgartown, Oak Bluffs (Gingerbread Houses). Vineyard Haven (where ferry comes in). If time do the whole island circuit and see Menemsha, Aquinnah-Gay Head Cliffs and Lighthouse. West Tisbury is pretty village.
  • Stay longer and visit Nantucket and Chappaquiddick
  • Accommodation: Harbor View Hotel – beautiful hotel, well located – highly recommended.

Drive Edgartown to Newport, Rhode Island
When leaving Martha’s Vineyard, it is highly recommended to make a booking on the ferry between Vineyard Haven and Woods Hole. We arrived at Vineyard Haven at 11.20am to buy tickets for the 12 noon ferry and found ourselves on standby. Unfortunately there was no space on the 12 noon so we had to wait for the 1.15pm ferry! 

It was a pretty drive to Newport – seeing the last of the Autumn foliage.

Newport, Rhode Island
We stayed for 2 nights in Newport and wished we had a third night! The highlight of our stay was visiting the mansions. There were 5 mansions open to the public but we only had time to visit 3 of them. There is an excellent Visitor Information Centre in Newport (in walking distance from the Newport Bay Club & Hotel) – where we were able to get details of mansion tours, catch the Trolley Tour, etc.

Highlights of a visit to Newport:

  • Drive Golden Mile
  • Visit the Mansions – We visited The Breakers, The Elms and Rosecliff
  • Cliff Walk
  • 11am Viking Tour – the Newport Trolley Tour (the Scenic Overview Tour)
  • Accommodation: Newport Bay Club & Hotel – great location

Drive Newport Rhode Island to Montauk on Long Island (Hamptons)
We had two days before we were due in New York City so we decided to stop over for one night in the Hamptons – a very fleeting visit.

The drive from Newport to Montauk was an interesting trip as we took a series of car ferries. The first ferry was from New London to Orient Point (Cross Sound Ferry) – a 45-minute trip during which we left the car and sat in the passenger deck (good facilities including nice food, TV room). Next was a short crossing (about 7 minutes) from Greenpoint to Shelter Island (the North Ferry Co),  then another short crossing (about 5 minutes) from Shelter Island to North Haven (South Ferry Co). From North Haven it is about 3 miles to Sag Harbor.

Sag Harbor is a pretty town – the first of a series of attractive ‘Hampton’ towns and villages. From Sag Harbor we took an hour to leisurely drive to Montauk (to drive without stopping would take about 30 minutes).

Montauk is at the eastern tip of Long Island peninsula – the furthest point we can drive. Our plan was to drive to the end of the peninsula to get a feel for the area – stay one night then drive back to NYC.

Highlights in Montauk include:

Drive from Montauk through the Hamptons to New York City


  • Drive through the Hamptons to see beautiful mansions behind hedges – Further Lane, East Hampton
  • East Hampton town – beautiful town, elegant shops
  • Citarella Gourmet Grocery Store, East Hampton – recommend for lunch
  • Amagansett – lovely town
  • Bridgehampton – very pretty
  • Sag Harbor

Stay longer to see:

  • Jackson Pollock’s house (Pollock-Krasner House & Studio) Open May-Oct Thu, Fri and Sat only
  • Parrish Art Museum

The Hamptons warrants a stay of many days to do justice to this beautiful area.

At the time of our visit (November 2016) it was about a 2.5 hour drive from East Hampton to NYC.

New York City

  • Accommodation: 4 nights Cambria Hotel, Chelsea – highly recommended
  • Walk the Highline
  • Chelsea Market in old Nabisco factory (at one end of Highline in Meatpackers)
  • 9/11 Memorial
  • World Trade Center Transportation Hub (the dove building)
  • Hop on Hop Off City Lights tour
  • Carol King musical – recommended
  • East River Ferry to Brooklyn or walk across Brooklyn Bridge – Grimaldi’s Pizza or Juliana’s Pizza
  • Walk Chelsea and Greenwich
  • Hop on Hop Off NYC Tour
  • Stardust Diner is fun
  • For more to see and do in NYC visit our blog New York in Winter

While the main purpose of this trip was to tour the New England Fall towns and visit the coastal area between Boston and NYC, as mentioned, an excellent airfare became available from Boston to Iceland. For details of our 10 day trip to Iceland (flying Boston – Reykjavik – Boston), please see our blog – Iceland Ring Road Tour.

For more details on a ‘leef peeping’ trip to New England, or the scenic coast between Boston and NYC, please contact
October/November 2016