10stop

My ultimate 10-stop US road trip guide with whale-watching and live music bars

FROM pretty colonial towns and buzzing cities to rugged coasts, sandy beaches and beautiful mountains, there is nowhere quite like New England.

And the best time to see it is in the Fall (autumn), when the leaves turn red and gold and you can do a bit of whale watching, too.

The colourful autumnal shades across New England Credit: Getty
Enjoy majestic whale-watching Credit: Getty

New England’s six states – Massachusetts, Maine, Vermont, New Hampshire, Connecticut and Rhode Island – are all quite different but add up to one amazing holiday experience.

It is one of the ultimate bucket list trips and doable – if you plan carefully.

We decided to cover all six states plus Boston in one mega two-week, 600-mile round trip.

It can be done – New England is small enough to fit into Texas four times over.

WAIL OF A TIME

I drove Irish Route 66 with deserted golden beaches and pirate-like islands


TEMPTED?

Tiny ‘Bali of Europe’ town with stunning beaches, €3 cocktails and £20 flights

We didn’t see eveything, obviously, but we had a damned good go!

WHAT YOU NEED TO KNOW

GO AT THE RIGHT TIME. New England’s Fall officially runs from September to November, with late September and October being the peak.

Don’t go too late or, as locals put it, you run the risk of it being “stick season” when all the leaves have dropped off.

However, whale watching ends late September/early October, so to see both, you need to time it right.

A lot of it’s down to luck.

GO ANTI-CLOCKWISE. If you want to see the best foliage, head north up the coast to Maine, across to Vermont, then drive back through New Hampshire, Massachusetts, Connecticut and Rhode Island.

The leaves start turning in the north first, so you will essentially be following the trees as the colours change.

DRIVE…BUT DON’T DRIVE. New England roads are a pleasure.

Petrol is still cheap, car hire is affordable and roads are wide, well maintained and signposted, and not that busy.

But DON’T drive in Boston – the traffic is horrendous and there is nowhere to park.

Make Boston either the start or the end of your trip so you aren’t stuck there with a car.

GO: NEW ENGLAND

GETTING THERE/ STAYING THERE: America As You Like It (americaasyoulikeit.com/020 8742 8299) has a 14-night fly drive from £2,930pp, including return flights, car hire and accommodation.

This includes two nights at the Sheraton Boston, one night at The Breakwater Inn & Spa, Kennebunkport; two nights at the Portland Regency Hotel & Spa, Portland, Maine; two nights at the Newfound Lake Inn, New Hampshire; one night at Cranmore Mountain Lodge, North Conway, New Hampshire; three nights at Hotel Champlain Burlington, Vermont; two nights at the Chart House Inn, Rhode Island; and one night at the Marriott Quincy.

MASSACHUSETTS

Visit the United First Parish Church – the only place where you will get so close to a presidential tomb Credit: Alamy

THE big draw in Massachusetts is Boston (see City Q&A) but there’s plenty more to see.

Beautiful Cape Cod, where the Pilgrims on the Mayflower first landed, is full of pretty little towns, sandy dunes and marshes that are teeming with wildlife.

We hit the resort of Sandwich and, as it was out of season, had the beach to ourselves.

The buzzing town of Quincy is worth a look, too.

It is best known for being the birthplace of two US presidents, John Adams and his son John Quincy Adams.

You can see their crypts in the United First Parish Church – the only place where you will get so close to a presidential tomb.

But nothing is as good as whale watching. The fishing port of Gloucester is THE place on the New England coast to see them, thanks to its proximity to three rich feeding grounds.

One whale would have been fantastic, but we saw EIGHT – a mixture of humpbacks and minkes – surfacing so dramatically they could have been performing for the cameras.

And you can get unbelievably close to them.

The boat crew will fill you in on how these gentle giants live, and even who they are.

They can identify each one by the marking on their fins.

If we hadn’t managed to see a single golden leaf during our trip, it wouldn’t have mattered after this. The absolute highlight.

WE STAYED AT: Quincy Marriott (marriott.com).

MAINE

Kennebunkport at Walker’s Point is worth a look Credit: Getty

THE state flag of Maine has a moose on it but it probably ought to be Pennywise the clown.

Yup, Maine is Stephen King country – and you can see why.

Its forests, small colonial towns and rugged coastline have a vaguely eerie quality that the writer has exploited to the full.

We stayed in Portland – King’s hometown – a working lobster port that’s also a laid-back city full of refugees from the 9-5 grind of New York and Boston.

There’s an appealing, alternative, hippy vibe and it’s great for bars with live music (try the local Alagash beer) and restaurants selling fresh lobster.

The rolls here were the best we had all holiday.

Kennebunkport couldn’t be more different.

It’s a pretty, upmarket town, whose main claim to fame is that it is the summer retreat of the Bush presidents.

It is a very touristy, chocolate box kind of place, full of art galleries, craft shops and tearooms.

It’s a bit like a US Bourton-on-the-Water.

Eat at the upscale Port Fish & Chop House restaurant. It’s a Bush favourite, apparently – ours too.

By the way, the Bush compound is just around the headland from Kennebunkport at Walker’s Point and is worth a look.

Don’t linger there for too long, though – the Secret Service are liable to suddenly pop up out of nowhere to check you out. 

WE STAYED AT: The Breakwater Inn & Spa, Kennebunkport (breakwaterinnmaine.com), and Portland Regency Hotel & Spa (theregency.com).

NEW HAMPSHIRE

Simon Copeland in Loon Mountain in the White Mountains National Park Credit: supplied

IT’S when you head inland from Maine to New Hampshire that the Fall hits you.

Nothing quite prepares you for the reds and golds, purples, oranges and coppers of the foliage – and there is so much of it.

Miles and miles of brilliant colours. It is everything we hoped it would be.

New Hampshire is prime “leaf-peeping” country – what the locals call the invasion of tourists who want to catch that EXACT moment the leaves turn.

Think bird-watchers are obsessive? You ain’t seen nothing.

A stop at Loon Mountain (named after loons, a duck-like bird, not the peepers) in the White Mountains National Park gave us the best chance to take it all in.

We took the gondola up to the top and spent a couple of hours trekking along the mountain trails (watch out for bears).

From the summit all you can see are beautiful colours in every direction.

Our B&B, a charming inn called the Cranmore Mountain Lodge in the middle of the park, was perfect for peeping and had another bonus – the chance to sleep in baseball legend Babe Ruth’s bed.

His daughter owned the place – putting the inn in innings, I guess.

And while you are in NH, try the sightseeing cruise on Lake Winnipesaukee, famously used as a location for the film On Golden Pond.

In a state full of sights to marvel at, this placid stretch of water with its many islands and mountain backdrop is one of the best.

WE STAYED AT: Newfound Lake Inn (newfoundlakeinn.com) and the Cranmore Mountain Lodge, North Conway (cmlnh.com).

RHODE ISLAND

The Breakers has 70 rooms, all astonishingly decorated and furnished, takes up more than 130,000 sq ft and was based on a 16th century Italian palazzo Credit: Getty

RHODE ISLAND may be America’s smallest state but it acts big.

It’s big on maritime history and big on seafood. It is also big on understatement.

Newport is home to some of the grandest and most opulent mansions ever built.

And do you know what locals call them? “Summer cottages”.

We toured The Breakers, the grandest of all.

It has 70 rooms, all astonishingly decorated and furnished, takes up more than 130,000 sq ft and was based on a 16th century Italian palazzo.

It was built by the Vanderbilt family, who made millions in railroads and steamships in the 19th century.

You can see more of these over-the-top symbols of the Gilded Age on the Cliff Walk.

This 3.5-mile path along the coast has crashing Atlantic Ocean waves on one side (the breakers) and the grand estates on the other.

Train magnate Vanderbilt might have been amused by another top attraction in Newport – the Rail Explorers.

This is a three-mile stretch of disused track that you pedal along on customised “rail bikes”.

On the way you can take in fantastic coastal views and may even spot the ospreys that nest in the area.

Newport itself is a charming port with a really vibrant quayside stuffed with bars and restaurants.

And do the sunset sail round the harbour.

You will head under the gigantic Newport Bridge which connects RI to Connecticut.

It’s such an amazing sight you will want to big it up.

WE STAYED AT: The Chart House Inn (charthouseinn.com).

CONNECTICUT

Head down to Mystic to learn about another one of New England’s guilty secrets – whaling Credit: Getty

VISIT New England and you could be forgiven for thinking everything is about the settlers and the Founding Fathers.

But the Mashantucket Pequot Museum will put you straight.

The Pequot were one of the original New England tribes – and almost totally wiped out by disease, slavery and massacre caused by the new immigrants.

It’s the darker side of the early American story, and well told at this fascinating museum.

The Pequot have had the last laugh, though.

The museum is next to the Foxwoods Casino, one of the biggest in America.

It’s owned and run by the Pequot, and it has made them the richest tribe in the US.

Head down to Mystic to learn about another one of New England’s guilty secrets – whaling.

The industry was so lucrative it made New England the Silicon Valley of its day.

Mystic – an attractive town that was the setting for the movie Mystic Pizza – was a major 19th century port.

Its brilliant Mystic Seaport museum recreates that great seafaring era and contains the world’s oldest surviving wooden whaling ship.

Go on board and get a taste of what it was like working in this terrible and hugely dangerous industry.

Thirty-odd men lived in tiny, cramped cabins often for years at a time.

The Captain, at least, had his own cabin (and toilet), as did his wife – the only woman on the trip.

WE STAYED AT: Hilton, Mystic (hilton.com).

VERMONT

The buzzing city of Burlington, on the shores of Lake Champlain Credit: Getty
One of Frank Sinatra’s greatest recordings is Moonlight In Vermont Credit: Getty

I’M a Frank Sinatra nut and one of his greatest recordings is Moonlight In Vermont.

I’m not 100 per cent sure Frank ever actually went there (not trashy enough for him), but, hey, it doesn’t matter.

I know from the song this state is something special.

Vermont invented leaf-peeping with canny marketing in the 1950s that promoted an overlooked season into something special.

And it is here that the trees are maybe at their best.

The vibrant colours are set off by the white-painted clapboard of the houses and churches in colonial villages and towns.

We headed across rolling farmland that could be in Old England to the buzzing city of Burlington, on the shores of Lake Champlain, via a stop at Hildene in Manchester, the family home of President Abraham Lincoln.

It’s certainly worth a detour as it tells one of the great American rags-to-riches stories and contains possibly the nation’s most famous political symbol – Abe’s stovepipe hat.

But the highlight was the scenic village of Dorset, and our stay at the homely yet lively Dorset Inn – Vermont’s oldest tavern.

If you’ve seen that great old movie White Christmas, with Bing Crosby, this is the kind of place it’s set in.

In fact, a stay at the Dorset may be the ultimate Vermont experience.

WE STAYED AT: Hotel Champlain Burlington (hotelchamplainvermont.com) and the Dorset Inn (innsofdorset.com).

SPILL THE TEA ON BOSTON

Boston is famously America’s most Irish city, but it may be its most English too Credit: Getty
Classic TV comedy Cheers starring Ted Danson Credit: Getty

BOSTON is famously America’s most Irish city, but it may be its most English too.

With its green spaces, historic buildings and cobbled streets, the centre can feel like London or Cambridge.

Indeed, Boston has a Cambridge – along with a Brighton, a Hyde Park, a Chelsea and a Dorchester.

The city itself, a major US port, was named after Boston in Lincolnshire.

And thanks to its ties to the American Revolution, England still looms large.

Boston and Massachusetts may have been instrumental in the rebellion that ended George III’s rule over the 13 American colonies, but they have kept large parts of our culture.

This year, Boston has been celebrating its role in 250 years of American Independence, even though the actual 1776 Declaration document was signed 300 miles away in Philadelphia.

As Bostonians like to joke, Boston did all the hard work, while Philly just did the paperwork.

Thanks to the anniversary – and the World Cup, of course – Boston (or Baw-stin, as they seem to pronounce it) has rarely had such a high profile.

WHY SHOULD I GO?

Whether you are a history buff, culture vulture, sailing enthusiast, sports nut, foodie or an enthusiastic pubgoer, Boston has something for everyone.

In the autumn you can see it at its best. Summer is too hot, winter too cold. In the Fall, the weather is still warm enough for shorts but the foliage is turning, making this attractive city even more so.

Boston is one of America’s most fascinating cities, and its European feel gives it a familiarity that’s uncommon in the rest of the US.

It’s an intriguing mix of the blue collar and the blue blood, as the city is both proudly working class and defiantly Old Money. It’s also very studenty – Harvard and the Massachusetts Institute of Technology are just over the Charles River.

One thing to remember, though – Boston ain’t a “Have a nice day” kind of town. Bostonians can be brusque and wrapped up in themselves – so quite a lot like Londoners.

STREETS MADE FOR WALKING?

Absolutely – and you really don’t want to drive in Boston (see box, above). Unlike New York or Chicago, with their easy-to-navigate grid systems, old Boston developed without the help of town planners.

That means the higgledy-piggledy central streets haven’t changed much since the 18th and 19th centuries. Rubbish for cars, great for walking.

In Beacon Hill, for example, you will find quaint cobbled alleys full of original gas street lamps, wrought-iron balconies and pretty red-brick terraced houses.

The centre is surprisingly small and easy to cover on foot. And the best way to get to know it is on a walking tour.

Try the 2.5-mile Freedom Trail walk, which offers a potted history of the fight for independence. It takes in 16 landmarks, including the Massachusetts State House, Founding Father Paul Revere’s House, the Battle of Bunker Hill Monument and the Boston Massacre site.

ANYTHING FOR THE BUCKET LIST?

Loads. Head to Fenway Park to catch a baseball game at the oldest stadium in America, home of the Red Sox.

Art buffs will love the Isabella Stewart Gardner Museum – a large private collection donated to the city by an eccentric millionaire – housed in an incredible Venetian-style palazzo.

The huge and immaculate Boston Common, America’s oldest public park, will give you some rare moments of calm in the middle of this bustling city.

View Boston offers a 360-degree panorama of the skyline from the 52nd floor of the Prudential Building in Back Bay.

If you have time, take in the city centre’s main neighbourhoods.

North End, on the waterfront, is a buzzing Little Italy full of trattorias, gelatarias and rival bakeries selling “Boston’s best cannoli”. Back Bay has charming squares and impressive Victorian brownstone town houses.

Beacon Hill has pretty, upmarket streets with boutiques and high-end restaurants, and South End is the place for trendy bars and bistros.

WHERE SHOULD I EAT?

Boston is known as Beantown – a clue to its speciality: slow-cooked beans with molasses and pork. Seafood is also a big draw here, ranging from New England clam chowder to lobster rolls and fresh oysters.

We headed to North End for a cosy, traditional family-run Italian trattoria, Bacco (bacconorthend.com) with fantastic food and craft beers.

And we particularly loved Pagu (gopagu.com) in Cambridge, which mixes Japanese and Spanish tapas (who thinks of these combinations?!) to mouth-watering effect.

If you have one big blowout in Boston, THIS is the place to go. Superb.

I FANCY A DRINK!

Another tradition from the old country Bostonians embrace is the pub culture. From English taverns to Irish pubs and trendy bars, drinking is BIG here.

And then there’s Cheers. The bar that inspired the classic TV comedy starring Ted Danson used to be called the Bull and Finch and is now a tribute act to the sitcom. It’s worth a look – even if it’s only a selfie in front of the sign.

Oh, and Bostonians DO drink tea – despite tipping loads into the harbour in the famous 1773 Boston Tea Party to protest against English taxation.

WHERE SHOULD I STAY?

We stayed at the Sheraton Boston Hotel in Back Bay (marriott.com) – a modern, comfortable hotel with great views across the Charles River and into Cambridge.

It’s an excellent base for discovering further and an easy walk into the centre along the attractive, tree-lined Commonwealth Avenue.

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