Boston fly-drives


By Eloise Barker

Photography by J. Greg Hinson / Getty Images

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July 2017

Nowhere in America has such a rich visual language as the six states of New England: land of lobsters and lighthouses, clapboard houses and autumnal forests, wild coastlines and historic cities. Go from Boston, gateway city to the region, and explore the fruits of the seasons in New York, Cape Cod and Vermont.

Boston to New York

Best for: Spring cities

The journey: 216 miles

Arrive in Boston for a spring break and stroll on the campus of Cambridge. After enjoying the sunny banks of Boston Common and buying a wardrobe’s worth of clothes in Back Bay’s shops, it’s time to show them off somewhere bigger. New York is the wisecracking younger brother of bookish Boston. If you want to ramp up the shows and sights after bumbling around in historic Boston’s cobbled streets, then head south and drop off your car in New York. Then you can hit the shops in the Meatpacking district, catch a Broadway show or see a world-class exhibition on the Upper East Side.

Saunter over to Staten Island or Coney Island for a breath of fresh air and a funfair. In spring, enjoy the St Patrick’s day parade, the start of baseball season and walking out in the elevated urban gardens of New York’s High Line.

Stay at: The Standard Highline, New York, a sparkly high rise with beautiful views over the Hudson. Make sure you grab a drink in the bar for sunset.

It starts in September in the northernmost mountains of Vermont. Visitors flock to follow the changing foliage as it spreads like wildfire down through the red, black and sugar maples of the White Mountains.

  • Cape Cod. © Christopher Seufert Photography.

    Kick back in Cape Cod

    Cape Cod’s population increases threefold when summer comes. The fifteen towns swell with visitors and the battered houses fling open their doors.

  • Deserted boardwalk on Coney Island, Brooklyn, NYC, USA. © Moussa81.

    Boston to New York

    Get to New York in time to see all its sights. Book flights to Boston from£1269 one-way

    Book flights
  • The Mayflower II, a 1956 replica, is docked in Plymouth Harbour. © Ken Wiedemann.

    To be a pilgrim

    Remembering the ship that brought the first pilgrims to America in 1620, this Mayflower Replica has been restored in time for 2020, the 400-year anniversary of Plymouth town.

    Stay in Plymouth

Boston to Hyannis

Best for: Summer hideaways

The journey: 70 miles

In summer, Boston’s walkable streets become spaces for outdoor living – whether you attend a festival at Seaport, summer concerts at the Memorial Hatch Shell on the Esplanade, or simply sit outside on the terraces at Faneuil hall. After you’ve made the most of this boutique city, it’s time to head coast-wards to Cape Cod. En-route, stop for a naval history lesson in Plymouth – this is where pilgrims bravely disembarked the Mayflower and started lives in America.

On to Cape Cod, which has miles and miles of America’s best beaches, punctuated only by stout lighthouses. Drive past modest sea captain’s houses in search of an avalanche of ice cream from a general store. Cycle along the rail trail through the pine trees and stop for lobster rolls or take a day trip to Nantucket and Martha’s Vineyard, where the well-to-do have their holiday homes.

Stay at: Doubletree by Hilton Cape Cod based in Hyannis, the perfect starting point for visiting the local area by car or ferry. A short boat trip can take you over to Nantucket and Martha’s Vineyard and the coast of Cape Cod is a short drive over the dunes.

Boston to Salem, Portsmouth and the White Mountains

Best for: Fall foliage

The journey: 143 miles

It starts in September in the northernmost mountains of Vermont. Visitors flock to follow the changing foliage as it spreads like wildfire down through the red, black and sugar maples of the White Mountains. As the trees change, the harvest comes in and townspeople celebrate with cranberry, grape and apple festivals.

Just 17 miles from Boston, visit Salem for tales of witchcraft that will disturb even the quietest mind, especially around October, when tourists gather in droves for the month-long Haunted Happenings festival. You can watch live re-enactments of the witch trials and fall for phoney tarot readings. Witchy business indeed.

  • The Goult Pickman House, Salem's oldest building. © D. Trozzo / Alamy Stock Photo.

    Something unnerving

    The small, casement leaded glass windows on this 17th century house look uninviting, but they were built out of necessity: glass was very scarce in the colonies. Next to this clapboard house is Old Burying Point Cemetery, where a Witchcraft Trails judge and a Mayflower passenger are buried.

    Drive to Salem
  • Walkway at The Flume gorge, Franconia Notch State Park, New Hampshire, USA. © Noppawat Tom Charoensinphon.

    Gone fishing

    Legend has it that 93-year old Jess Guernsey was out fishing when she stumbled upon Flume Gorge in 1808. Her discovery is one of America’s great natural wonders. Walk the two-mile trail for viewpoints of Mount Liberty.

    Fly into Boston
  • Stowe Village Church. © Ken Wiedemann.

    Slow down in Stowe

    And appreciate its turning trees in Autumn and its ski village in winter.

    Read about ski in Stowe

Drive north to Portsmouth, which has a perfectly recreated 17th century village, Strawberry Banke, where you can play Puritan for a little while and then explore the USS Albacore, a naval submarine. Wave farewell to the waves and head inland to the White Mountains. The dramatic peaks of New Hampshire are lined with walking trails. You can take a scenic drive from North Conway towards Chocorua Lake, where the pointy peak of Mt. Chocorua rises above the red trees. Follow the wild river at Flume Gorge’s short walking trail and keep your eyes peeled for moose, black bear and photo opportunities when you pass under the iconic covered bridges on the woodland roads.

Stay at: The Liberty Hotel, Boston puts on a yearly Halloween party where even the demons retain a sense of class.

  • Aerial of the High Line Park in New York, USA. © Alija.

    Walk the line

    From Boston to New York, where you’ll find an unusual garden in the city. Book flights from London to Boston, plus a ten-night hotel stay from:£612 pp

    Book flights and hotels

Boston to the slopes

Best for: Winter powder

The journey: 199 miles

In winter, Boston’s streets are banked with snow and there’s nothing more tempting than a cosy Irish pub, followed by shopping the sales at Downtown Crossing and skating on Boston Common’s Frog Pond. Then, make your getaway to the mountains of Vermont. The town of Stowe sits below the slopes of Vermont’s highest mountain. The ski slopes are six miles away, so having your car is useful to reach Mount Mansfield and Spruce Peak. 13 lifts take you up into the snow and over half the runs are perfect for intermediate skiers. Cruise along Perry Merril for stunning views whilst you schuss. Après ski comes courtesy of the Matterhorn ski bar and breakfast should be rounded off with a maple syrup-soaked waffle, suitable fuel for the slopes.

Stay at: Stowe Mountain Lodge. Based in Stowe alpine village, this lodge has easy slope access. Out of powder season, arrive in September and October and you’re in prime position for leaf peeping: Vermont has the most glorious Autumn foliage.