Boston fly-drives by season

By Eloise Barker

Title photography by J. Greg Hinson / Getty Images

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The six states of New England are wonderful all year round: discover a land of lobsters and lighthouses in the summer, or clapboard houses and autumnal forests in fall. Go from Boston and explore New York, Cape Cod and Vermont: we’ve got a trip for every season.

Boston to New York

Best for: A springtime twin-city break

The journey: 216 miles

New York is the wisecracking younger brother of bookish Boston. Both cities are magical in springtime, and you can drive between them in half a day. Start in Boston, where you can stroll on the pleasant campus of Harvard in Cambridge or enjoy the sunny pathways of Boston Common. If you fancy shopping in the city, you can buy a whole wardrobe’s worth of clothes in the shops at Back Bay: perfect if you fancy rocking up to New York in a brand-new outfit.

After dropping your hire car off in New York, saunter through Central Park on foot for cherry blossom and sprawling lawns. In spring you can enjoy the St Patrick’s Day parade, the start of baseball season and walking through the elevated urban gardens of the High Line.

Stay at: You might be in the big city now, but there’s no need to choose an impersonal hotel experience once you arrive in New York. Hotel Indigo Lower East Side NYC is quirky and urban, with its own rooftop bar and swimming pool.

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.
  • 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 from the Mayflower and started lives in America.

Heading onwards to Cape Cod, you’ll find miles and miles of America’s best beaches. All along the shore sit charming clapboard buildings: modest sea captains’ houses, stout lighthouses, and general stores where you can buy yourself an avalanche of ice cream. Save room for the region’s special lobster rolls – and then burn off your East Coast feast by cycling along the rail trail – a track that takes you through fragrant pine tree woods and six Cape Cod towns. If you want to explore further, you can easily take a day trip to Nantucket and Martha’s Vineyard – tiny islands where the well-to-do have their holiday homes.

Stay at: Holiday Inn Cape Cod Hyannis enjoys a heated indoor pool, whirlpool and seasonal outdoor pool, plus the delights of dinner and drinks in the Mad Hatter lounge. It’s also a great choice for budget-conscious travellers.

Boston to Salem, Portsmouth and the White Mountains

Best for: Fall foliage

The journey: 143 miles

In autumn, you’ll need to leave Boston to see the best sight of the season: New England’s famous fall foliage. 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 our ski holidays

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. Next, 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 wild moose, black bear and photo opportunities when you pass under the iconic covered bridges on the woodland roads.

Stay at: The trendy YOTEL Boston is full of fun modern gimmicks: there’s a robot at reception and mood lighting and a monsoon shower in your room.

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

    Walk the line

    Head from Boston to New York in spring, and you’ll discover the High Line, an unusual park in the city.

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 in 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. There are 13 lifts to whisk you up the slopes, and over half the trails in the area are perfect for intermediate skiers. Cruise along Perry Merrill, a long, gentle blue run named after the state official who pioneered skiing in Vermont. You’ll be rewarded with stunning views while you carve up the slopes.

Fifteen minutes from Stowe is Waterbury, the home of Ben and Jerry’s ice cream. The famous factory runs tours – even in winter, so diehard fans can still sample a scoop in the snow. Don’t miss the funny ‘graveyard’ of discontinued flavours (featuring monuments to the forgotten delights of ‘Aloha Macadamia’ and ‘Holy Cannoli’).

Stay at: Stowe Mountain Lodge is actually based in Stowe’s alpine village, so it’s right on the slopes. It’s a large hotel with multiple bars and restaurants, and the ski valet – who guards your winter gear when you clock in for apres-ski – is a lovely touch.