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Great Escapes for Discerning Drivers

New England Fall Colours Tour

19 September 2020 - 10 October 2020

New England is well known as a distinctly American region rich in history, culture, and natural beauty. It is particularly known for its brilliant autumns (fall) to drive lazily through mountains blanketed with gold-and-red foliage. There are also plenty of other things to do such as stopping at country stores, orchards, local restaurants, wandering through antique shops lining a peaceful village green, exploring the museums and shopping of the cities, or to get a head start on some cool day hikes in the mountains and countryside. This three week tour will start on Long Island, near the famed North Shore. Drive across Long Island for a night in the Hamptons. Take the ferry to Connecticut before heading to Newport, Rhode Island for two nights. Explore Cape Cod and the fabulous city of Boston for a few days, and then drive north up the Maine coast to Camden. The tour then turns inland, across Maine and New Hampshire to Mount Washington and onto Stowe, Vermont, giving plenty of time to take in the mountains. Enjoy a weekend in southern Vermont in true New England style. The tour winds it way south, through Massachusetts and the Berkshires, then finally through Connecticut back to Newark (for those shipping cars) and New York. The final night of the tour will be in New York, with an option to extend your stay for those who wish to take a bigger bite of the Big Apple.

Our carefully chosen route ensures that we pass by some lovely places to see and visit each day. We stay off the main roads and highways as much as possible, and the traffic is light and the driving easy. We have written detailed route directions for your convenience, and describe all the sights to see and recommend places to visit or eat.

Cars from outside North America will be shipped to and from Newark, New Jersey. Shipping is not included, but we can arrange this on your behalf. Read more about shipping. Alternatively, you can hire a car in New York and join the tour.


• Beautiful beaches & coastline of Long Island, Cape Cod & Maine
• Fascinating, historic towns such as The Hamptons, Newport, Stowe, Woodstock & Deerfield
• Enjoy a sunset sail in Newport Harbor, Rhode Island
• Mansion visits in Newport, Rhode Island
• Sensational drives including Mount Washington, Kancamagus Highway, Equinox Skyline drive & Mohawk Trail
• Stunning scenery with lakes, mountains, coasts, countryside, villages & towns
• Be a ’leaf peeper’ and see the incredible autumn leaf colours
• Visit the world-famous cites of New York & Boston
• Climb Mount Washington
• Delicious seafood, lobsters, and seasonal foods
• Outstanding hotels, from wood shingle beach houses & mountain retreats to traditional weather-board village inns & luxury city hotels
• Visit 7 states: New York, Rhode Island, Massachusetts, Maine, New Hampshire, Vermont & Connecticut


Route map
Price: $TBC
Starts: 19 September 2020
Duration: 22 nights / 23 days
Mileage: 1,980 miles

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What's Included?

  • An extensively researched and carefully designed itinerary to optimise your trip
  • Tour book – includes a brief history of New England, emergency details, overview maps and detailed directions, accommodation information, and a very detailed account of everything there is to do, see and visit each day. The book eliminates the need for any other guide books.
  • Accommodation in superb, luxury hotels for 22 nights, including a full breakfast each morning. All taxes and other fees (and there are lots!) are included already.
  • Three-course dinners on 10 evenings. On the other evenings restaurant recommendations will be in the tour book and we can make reservations if required.
  • A half bottle of wine per person is also included with each dinner.
  • New England Road Atlas
  • Rally Plate & Regalia (quality rucksack embroidered with tour logo, stickers, luggage tag, pen/highlighter)
  • Mansion Pass for Newport, Rhode Island
  • Sunset sail on a classic yacht in Newport Harbor, Rhode Island (weather dependent)
  • A specialist classic car mechanic will accompany the tour with a van to carry tools, spares, and a limited amount of luggage. We also have contact network of classic car garages on route in case of any ‘failures to proceed’ or mishaps.
  • Experienced and friendly tour director, Sarah Dowding and assistant, to ensure the smooth-running of the tour


May be subject to change.

Day 1: 19 September 2020

Arrive in New York and stay overnight in a fabulous hotel in western Long Island. There will be a welcome dinner this evening. (It is also possible to arrive before if you wish to spend time in New York etc.)

Day 2: 20 September 2020 148 miles

Drive across Long Island, firstly via the pretty north shore then the Long Island Expressway to explore the chic Hamptons. Stay for two nights in a wonderful hotel in nearby Sag Harbor. Enjoy an afternoon walk on the beach, and drive around the exclusive residential areas to see many of the multi-million dollar holiday homes. Dinner is included.

Day 3: 21 September 2020 45 miles

Spend the day exploring Long Island. Drive out to the south fork and Montauk – for windswept wilderness, or just spend the day admiring the beautiful houses around the Hamptons, or top up your tan on the beach. Dinner is not included this evening.

Day 4: 22 September 2020 88 miles

Head up from Sag Harbor onto Shelter Island to Orient Point on Long Island’s North Fork and take the ferry across to New London, Connecticut. Drive along the coast, visiting the lovely town of Mystic, best known for its naval history and the wonderful Mystic Seaport, along the way.

Stay for two nights in a gorgeous hotel in the centre of Newport, Rhode Island, America’s yachting capital and a town renowned for its mansions. The hotel has a wonderful spa and pool, and is in easy walking distance of all the major sights. Dinner is not included on either evening in Newport as there are so many wonderful restaurants within walking distance.

Day 5: 23 September 2020

Spend the day exploring Newport, discovering some of the incredible mansions (ironically called ‘cottages’) that are ubiquitous in the town and along the cliffs. If you wish, enjoy the 3.5 mile cliff walk which allows you to see many of the mansions from their gardens, as well as being able to visit some of them to see the luxurious and gilded interiors.  This is a really charming town, with many wooden buildings dating back to the early 18th and 19th centuries, which gives a serene air to the numerous little streets. The waterfront has lots of lovely restaurants and bars to take in the sights and sounds of the marina and some stunning yachts. Try a sunset cruise (included) from 5.30-7pm on an 80ft pilot schooner for a sail around the harbour and Narangassett Bay.

Day 6: 24 September 2020 122 miles

Drive along the coast into Massachusetts. Head along the pretty south shore of Cape Cod from Falmouth to Chatham and stay overnight in a lovely inn right on the shore. It’s just a short stroll to the main street of this genteel village, which has galleries, stylish shops, and the Wild Goose Tavern for a well-earned beer or ‘sundowner’. Revel in the quintessential New England coastal style, with weather-board seafront houses and sandy beaches. Dinner is included.

Day 7: 25 September 2020 162 miles

Spend some time on Cape Cod, discovering the pretty villages, beaches and scenery on the way north to Provincetown in the far north of the Cape. Whale watching tours are on offer here too. Return back down and head along the lovely north shore, dotted with old fishing villages, before driving north to Plymouth, home of Plymouth Rock, often considered the landing place of Pilgrims in 1620. There is also a replica of the Mayflower boat. Continue into Boston and stay for two nights at a wonderful and luxurious hotel right on the harbour, with secure underground parking. The hotel has a fabulous pool and spa. Dinner is not included on either evening in Boston but there are so many restaurants to sample nearby.

Day 8: 26 September 2020

Enjoy exploring the cosmopolitan city of Boston. The city is the largest in New England and one of the oldest in the United States. Take a day off from driving and use the chance to see its superb museums, art galleries and perhaps a spot of shopping. Walk the Freedom Trail or take a trolley bus ride, to see the historic sights, such as Harvard University or the USS Constitution aka ‘Old Ironsides’.

Day 9: 27 September 2020 180 miles

Drive up the Maine coast, through lovely towns such as Ipswich, Portland and Kennebunkport, to Boothbay Harbor, itself a pretty fishing village. Stay for two nights in a delightful and charming hotel on the shore, a couple of miles from Boothbay Harbor, with gorgeous views of the bay. Dinner is included and will be a traditional lobster bake.

Day 10: 28 September 2020 151 miles

If the weather is good then there is the opportunity for a whale watching boat trip (3.5 hours) from Boothbay Harbor. There are humpback, blue, fin, minke, pilot and northern right whales off the coast.

Or relax for the day on the beach, take a kayak out to explore the bay, or take a circular tour to discover the attractive towns of Camden or Rockport, and other seaside villages in Maine. Dinner is at leisure and there is some great seafood to be enjoyed.

Day 11: 29 September 2020 155 miles

Head inland on some great back roads to the New Hampshire lakes region, skirting around the shores of Lake Sebago, and then driving around Lake Winnipesaukee. Stay for two nights at Mill Falls in Meredith at the north end of the lake, at a truly gorgeous hotel (and very popular – on our last tours no-one wanted to leave), with a superb ‘polished rustic’ interior, situated right on the shore. Enjoy a wander around Mill Falls, with it’s little shops and lakeside promenade, or savour the view from the outdoor hot-tub. Dinner is included. 

Day 12: 30 September 2020 165 miles

A circular drive  up to and around Mount Washington. Drive north to the White Mountains and drive up the auto road to the summit of Mount Washington at 6,200ft. The views are incredible and the colours really start to be noticeable here across the broad valleys smothered in the reds, golds, yellows and greens of the trees. Dinner is included at the hotel again.

Day 13: 1 October 2020 164 miles

Drive along the stunning Kancamagus Highway, which runs alongside the river and is a superb route for ‘leaf peeping’. Head through the Franconia Notch and onto Stowe, Vermont. Stowe is renowned as a ski resort but is wonderful at any time of year. It’s a small town surrounded by wide-open country and woods. Stay for two nights at an alluring hotel  with the most glorious views of the mountains, enhanced by an incredible spa, indoor and outdoor pools and hot tubs – a very decadent place to watch the sunset. Dinner is included this evening only.

Day 14: 2 October 2020 130 miles

Explore the Stowe area with a short circular tour through the Smugglers’ Notch, a very narrow, rocky route with fabulous views. This region is also known for its maple syrup production, and there are products aplenty to sample made with this beautiful sweetener from the surrounding trees.

Day 15: 3 October 2020 125 miles

Head south to Waterbury, home of Ben & Jerry’s ice cream (a must-visit for fans). Continue on to absolutely outstanding Shelburne Museum, known as ‘America’s attic’, and one of the best visits in New England – an outdoor museum-collection of over 30 buildings from across the region showcasing architecture and traditions. Next door is the Vanderbilts’ showcase Shelburne Farms. Drive south, crossing the mountains and drinking in the fall colours draped over the hillsides, punctuated with green, open meadows, jewel-like ponds and grazing cows.  As it is the long holiday weekend for Columbus Day we are staying for the next three nights in a wonderful and charming hotel in the centre of the gorgeous village of Woodstock. Dinner is included this evening only.

Day 16: 4 October 2020

Spend the day in Woodstock, either relaxing, or exploring the local area. There are some lovely walks, or enjoy pottering around pretty villages, browsing farm stalls and visiting museums and galleries. The driving is also superb, with drives over the Quechee Gorge, ‘Vermont’s Little Grand Canyon’, and snaking along river valleys. Visit the excellent Billings Farm, or Marsh-Billings-Rockefeller homestead, a true forerunner in environmental conservation.

Day 17: 5 October 2020 121 miles

Either enjoy another day relaxing or take a circular drive around the area. There is another scenic route that encompasses the homestead of fromer US President, Calvin Coolidge at Plymouth Notch. The route then passes Killington, the largest ski resort in the east USA.

Day 18: 6 October 2020 72 miles

Leave Woodstock and drive south for a shortish day heading south through the hills of old Vermont, stopping at the pretty village of Weston to visit the diminutive historical centre and the wonderful old-fashioned country stores, before heading on to Peru and Manchester. Just a little south of Manchester is Hildene, President Lincoln’s family home – well worth a visit. Drive just 6 miles further to Dorset, to stay for two nights in a really charming and delightful inn on the village green. Dinner is included this evening only.

Day 19: 7 October 2020 49 miles

Discover the area around Dorset with a circular drive filled with some glorious winding mountain roads, tempting stops and photo opportunities galore. Visit the smart outlet shops of Manchester for a spot of shopping, wander down the wide village green of Manchester Village, enjoy a stroll around the country’s oldest marble quarry which is now a beautiful lake, or explore one of the oldest general stores, which is like a step back in time. End the day sitting in a rocking chair on the front porch with a local drink such as hot apple cider or brew in hand.

Day 20: 8 October 2020 173 miles

Drive south through the Green Mountain National Forest and take the Equinox Skyline Drive, which offers magnificent views, the tightest hairpin turns in Vermont (this won’t impress Europeans as much), and an overlook of the only Carthusian monastery in North America. Cross into Massachusetts once more and from North Adams take the Mohawk Trail east to visit the pretty and historic town of Deerfield, with many old houses to visit.

Drive across the Berkshires to Lenox and stay for two nights in a beautiful traditional inn on the edge of town. Dinner is at leisure on both evenings and there are a number of great restaurants within a few minutes walk.

Day 21: 9 October 2020 28 miles

Explore the area around Lenox with a wonderful drive through forested countryside in the Berkshire hills. The day starts with a trip to the Hancock Shaker Village, with its numerous original buildings and barns. Continue south to Stockbridge, home of the Norman Rockwell Museum, one of the country’s most famous artists, with his classic take on Americana life. Take the time to also visit Naumkeag,  to experience Gilded-Age style and splendor at this marvellous estate, renowned for its whimsical gardens and rare Berkshire “Cottage.” Dinner is not included.
Mileage: 28 

Day 22: 10 October 2020 163 miles

For the final day drive south into Connecticut and visit the lovely villages of West Cornwall and Kent.

Our final night of the tour will be spent at a fabulous, contemporary hotel in the area of Hoboken (Frank Sinatra’s birthplace) in New York, situated right next to the Hudson River. The hotel overlooks the iconic Manhattan skyline with views of the Empire State Building, as well as the whole of Manhattan from the George Washington Bridge along to the Statue of Liberty. There is a farewell dinner this evening.

Cars will be collected from the hotel for transport back to the UK.

Day 23: 11 October 2020

Depart for the airport and/or home. We can also arrange the option to extend your stay, to allow more time to visit New York. Or take an overnight flight on Sunday and enjoy a full day in Manhattan.


We have hand-picked some beautiful, quality character hotels with great charm, in superb locations across New England. From old cedar-shingle coastal properties and exquisite village inns to luxurious mountain lodges and contemporary city hotels. All, of course, have suitable parking for our cars. In most places we shall be staying two nights, with some one-night stops only occasionally. Rooms are well appointed and generously sized (especially by European standards), beds are enormous (6ft plus doubles, or two queen beds) and blissfully comfortable, and the food superb – both dinners and breakfasts, with plenty of choice. All the hotels are in lovely areas that we know you will enjoy.

What’s Excluded:

  • Twelve (12) evening meals. Recommendations will be made in the tour book and reservations can be made if required.
  • Ferry from Orient Point, Long Island to New London, Connecticut (as reservations for groups cannot be made)(approx $80)
  • Entry to any attractions, museums, sight seeing etc, other than stated
  • Any lunches
  • Vehicle shipping is not included as the price varies depending on the size and value of the car. However, Classic Travelling will make all the arrangements for container shipping, marine insurance, customs and handling on your behalf. (In 2015 it was an average of just under £4,000 GBP per car return, including shipping, handling, customs, marine insurance etc. The price varies on your vehicle value.)
  • Car hire/rental (if you choose to do this instead of shipping). See below.
  • Motor insurance whilst in the USA as the price varies depending on the car. However, all the arrangements will be made on your behalf, unless you tell us otherwise. (In 2015 it was $558 per car for the tour, although this varies depending on the car’s value)
  • Flights to the USA. Classic Travelling does not offer flights and you will be able to find the best deals online. We recommend flying to and from JFK New York.

Shipping Vehicles

For container shipping the price is going to be in the region of £4-5,000 per car return, including all insurances, temporary import bonds etc. We can only get an accurate price once we know your car’s length and value. To compare this with car hire in the States, it is about $2,500 USD to hire a Chevrolet Corvette per week, (Budget Car Hire). We have had quotes for classic car hire such as a 1966 Mustang convertible or 1957 Speedster replica which will be $9,000 for the tour duration. Which then makes shipping your own classic or sports car comparatively cheap! Read more… 

Car Hire/Rental

It is also possible to hire a car in New York and join the tour. To hire an American icon, such as a Corvette or Mustang (modern cars) is a similar price to shipping. For example, Avis offer Mustang hire for three weeks from £1,830 if you pay in advance. There are a few US car hire companies that offer such cars.


  • All passports must be valid for six months after the end of the tour. You will also need your vehicle registration documents, driving licence (a photo-card licence or international permit is best), and an international insurance green card.
  • It is advised to obtain IDPs (International Drivers Permits) before coming to the United States. It is worth noting however that these IDPs are only ‘translation documents’ and should always be accompanied by a current, valid driver’s license at all times. Varied rules and regulations (in regards to these IDPs) are used by police departments all over the United States.
  • International travelers who are seeking to travel to the United States under the Visa Waiver Program (VWP) are now subject to enhanced security requirements and will be required to pay an administrative fee. All eligible travelers who wish to travel to the U.S. under the Visa Waiver Program must apply for authorization, which is $14USD per person and valid for two years. Click here for details.
  • However, the most important requirement is that you take pleasure in motoring through fabulous scenery, relish individual, character hotels and enjoy the company of like-minded travellers.



Prices are to be confirmed. Please contact us to register your interest in this tour.
Prices are based on two people sharing a double or twin room

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