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.

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.

Drive NYC to Hancock


  • 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




While in Hancock area:


  • Village Bike Rentals: Ashuwillticook Rail Trail
  • Whitney’s Farm – 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 drive takes in:

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


  • 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


  • A bit out of the way. Perhaps spend more time in areas where foliage is more scenic.
  • Accommodation: Air BnB “Blue Building with Neighborhood Character”

Drive Burlington to Montreal


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

  • 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 drive passes through pretty villages including Tamworth and Center Sandwich.


  • 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

Drive Boston to Edgartown (Martha’s Vineyard) via Plymouth


  • This was a lunch stop but would be worth spending a night
  • 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

Edgartown, Martha’s Vineyard

  • Very beautiful town – pretty location, 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

Newport, Rhode Island

  • Drive Golden Mile
  • Visit the Mansions – We visit 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)


  • Montauk Point Lighthouse & Museum & Gift Shop & Café
  • Accommodation: Montauk Manor – at tip of south fork of Long Island

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

On this trip we only had one night in Montauk then drove through the Hamptons on the way back to NYC. The Hamptons warrants a stay of many days to do justice to this beautiful area.

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, an excellent airfare became available from Boston to Iceland. As a result we took a side trip: Boston – Reykjavik – Boston. Please see our blog – Iceland Ring Road Tour.

Photos of New England Fall – October 2016
October/November 2016