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The Best Road Trip Through New England

| Travel Ideas, United States

The Best Road Trip Through New England

Researching a trip to the States led me to New England – six states that make up the region, all offering something a little different – yet all connected by legendary history, spectacular scenescapes, quaint villages and delicious seafood.

Boston Pit Stop (2 nights)

Trains leave Penn Station, NYC regularly to Boston with the Acela Express taking just 3.5hrs arriving at either Back Bay or South Station, depending where you plan to stay.  Allow at least two days to explore what is one of the oldest cities in America, founded as early as 1630.

The road trip starts with two full days in Boston, just enough time to explore what is one of the oldest cities in America, founded as early as 1630. And don’t worry, if you run out of time, schedule in a few more days at the end of your trip. Compact and easy to get your bearings, wander the cobblestone streets of Beacon Hill, follow the 2.5 mile red line of the Freedom Trail which links 16 Colonial-era landmarks, step inside the Paul Revere House or seek out the ghosts of great patriots at The Warren Tavern in Charlestown, where George Washington, Benjamin Franklin + Paul Revere were known to imbibe, then time travel to a different bar – Cheers, the iponymous TV show just opposite the Boston Common.

The commentary is first rate on the Boston Duck Tour – getting both an informative and entertaining perspective from land and water on one of their famous amphibious vehicles; and children will love visiting the Boston Tea Party Ships & Museum re-enacting tossing tea into the harbour.  Boston Public Library is not to be missed, hear the voice of the 35th President at the John F Kennedy Library + Museum, explore the Museum of Fine Arts open until 10pm from Wednesday-Friday, or just around the corner the Isabella Stewart Gardner Museum – the central courtyard both a surprise and breathtaking and is where 13 masterpieces were stolen in 1990 still unrecovered and marked by empty hanging frames.

When it comes to food, be prepared to be overwhelmed with choice – from exploring the new area of Seaport with its converted warehouses, South Bay and its main streets lined with funky bars and tempting restaurants to some of the best coffee, craft breweries and do-nuts!

  • Boston Public Market:  features only products grown, raised or crafted in New England.
  • Eataly Boston: three floors of Italian – emporium with groceries, seafood markets and eateries.
  • Thinking Cup: in Newbury Street – coffee hits the spot and the latte art is a must see!
  • Neptune Oyster: no reservations, limited seating, worth the wait for great seafood.
  • Acquitaine:  a little bit of Paris in Boston at this cute neighbourhood restaurant in South Bay.
Visit the Isabella Stewart Gardner Museum in Boston

Visit the Isabella Stewart Gardner Museum – the central courtyard both a surprise and breathtaking

Visit the House of the Seven Gables in Salem

Visit the House of the Seven Gables in Salem


From Boston, head north to Salem, famous for the witch trials in colonial Massachusetts between 1692-1693, when more than 200 people were accused of practicing witchcraft. After a wave of hysteria a special court was convened to hear the cases, where tragically 20 were executed.

Tour the Witch House, the former house of Judge Jonathan Corwin and the only witch trial structure remaining in Salem. Then, step into Salem’s rich maritime history with a fascinating tour through the Peabody Essex Museum where you’ll see artefacts brought back from overseas by ship captains as well as other exhibits, including an authentic re-erected Chinese Qing Dynasty merchants’ house, the Yin Yu Tang House.

Discover The House of Seven Gables, a national historic landmark built in 1668, forever immortalised by the novel written by 19th century author Nathaniel Hawthorne. Added to the charm of the architecture is its famed hidden staircase and a spectacular three season colonial revival garden.

Gloucester detour

You may want to skip Salem and make a detour to the charming harbour town of Gloucester, settled in 1623, it is America’s oldest seaport and remains one of the busiest on the Eastern seaboard. On the edge of the harbour is The Fisherman Memorial and circling the monument are plaques with the names of those lost at sea from 1716 to 2001. Six of the most recent names are those of the Captain and crew from the fishing boat made famous in the book and film The Perfect Storm.

Enjoy a stunning drive through Massachusetts

Enjoy a stunning drive through Massachusetts


Alternatively, leaving Salem keep on the I-95 and stop at Portsmouth, NH situated on the Piscataqua River at the top of the 18 miles of New Hampshire’s white sand seashore.  Stunning riverside beauty, it is a little seaport city of bridges, bricks, baristas, bistros, boats, bountiful tax-free shopping and lots of history and culture – we are talking less than an hour’s drive from Boston.  Here, you’ll wander through the Strawbery Banke Museum exploring over 30 historic buildings that display New England’s architecture and learn traditional crafts from period-costumed artisans all while breathing in salty sea air

Kennebunkport pit stop ( 1 night)

Having left Massachusetts, passed through New Hampshire, arrive in Maine where you will love Kennebunk’s Lower Village and Dock Square located along the ocean and Kennebunk River. Settled in the 1600s and a long time ship building mecca, with images of five-masted ships and schooners making their way out to sea, this is where Sea Captains built fine mansions, many of which are preserved today as lovely inns. Dine at one of the many restaurants – put on a bib and eat fresh lobster, or perhaps a clam chowder.

The next day you’ll journey to Bar Harbor, where rich history meets stunning mountain scenery, but first a couple of detours to tempt you!

Portland detour 

Sometimes known as “the other Portland”, the one in Oregon was actually named after Portland, Maine and now one of the foodie destinations in the US with the city boasting four of the state’s five James Beard Award winning restaurants. With a population of just 67,000 it is said to have more dining options per capita than anywhere else in America. So why not time your arrival for lunch and try Eventide Oyster Co – award winning chefs Mike Wiley and Andrew Taylor’s tiny, busy seafood restaurant with a raw bar, lobster rolls and creative New England produce. With a no reservations policy, it may be easier to get into their other restaurant The Honey Paw, conveniently located next door.  Or head where the locals go to J’s Oysters on the waterfront for a bucket of ‘steamers’ (steamed clams) washed down with a craft beer.

Sometimes known as “the other Portland”, the one in Oregon was actually named after Portland, Maine and now one of the foodie destinations in the US
Put on a bib and eat fresh lobster in Kennebunkport

Exploring the docks of Portland Maine

Autumn at Strawberry Banke in Portsmouth

Autumn at Strawberry Banke in Portsmouth

Freeport detour

Approximately 20 minutes north of Portland is Freeport, a historic and picturesque village, located along the shores of Casco Bay and is best known for its fabulous name brand outlet shopping and home to the world famous L.L. Bean flagship store open 24/7 365 days of the year. (outdoor recreation). There are many locally owned shops and boutiques that offer “Maine-made” items, and if time allows, the Freeport Historical Society offers walking tours and demonstrations of its past, including a bar and quilt’s tour.

Bar Harbor pit stop (2 nights)

Sitting in an area of the Maine coastline referred to as “Down East” Maine, with a long history dating back over 200 years, you will hear the local accent where the ‘r’ sound is dropped, so their famous lobster is pronounced “lob-stuh”.  Also home to multiple historic mansions, Bar Harbor was once a popular resort destination for New England’s elite, today, it is best known as the gateway to Acadia National Park and with two nights here, the perfect place to relax and do what you please.

Acadia National Park 

There is a full day to explore one of the oldest and most beautiful national parks in America. Rocky coastlines, ferocious waves, and towering mountains are just the tip of what this park has to offer. Where to start? Perhaps at Sieur de Monts Spring with some gorgeous hiking trails such as Jesup Trail, the Wild Gardens of Acadia and the Abbe Museum and Nature Center.  Drive to the summit of Cadillac Mountain, the tallest peak in the park, for breathtaking views of the surrounding landscape and where, if you rise early, you can see the first sunrise over the US, and Frenchman Bay.

Explore Acadia National Park - you may even find a moose!

Explore Acadia National Park – you may even find a moose!

North Conway detour 

Heading back across Maine to the White Mountains in New Hampshire, also known as the “Rooftop of New England,” where you’ll wind through pristine wilderness and pockets of picturesque towns; cross historic covered bridges and hear the sounds of clear mountain streams.  Take a pit stop at North Conway in the heart of Mt Washington Valley which also happens to be home to galleries and factory outlets and stunning views across the Presidential Range to Mt Washington, Moat Mountains and Rattlesnake Bridge.  Follow the Kancamagus Highway, New England’s ultimate scenic drive to your overnight accommodation in the White Mountains.

White Mountains pit stop

An outdoor lover’s paradise.  Allow time to see the imposing Omni Mount Washington Resort, tour the Flume, a natural granite gorge. Get onboard the Cog Railway that climbs up to the top of mountain, the climbing train has been in operation since 1868 making it the first of its kind in the world. Alternatively, if you dare, and the weather is in your favour, drive the Mount Washington Auto Road for an unmissable experience. Better still, and safer, take a narrated van drive.  And give yourself enough time to explore some of the beautiful towns like Bethlehem and Littleton – home. And give walk through its pretty downtown, stopping at Chutters, home of the world’s largest candy counter and take a photo of your Glad Day at the Pollyanna statue.

You'll wind through pristine wilderness and pockets of picturesque towns; cross historic covered bridges and hear the sounds of clear mountain streams.

Williamstown pit stop

Your New England adventure continues west in the Berkshires. This rural region in the Massachusetts mountains is dotted with charming towns. A popular vacation spot, the Berkshires is where artistic, academic, and outdoor cultures collide. Head to the Berkshires town of Williamstown, known for its art institutions, where you’ll ponder world-class collections at the Clark Art Institute and the Williams College Museum of Art.  Or head to Mohawk Trail State Forest in Charlemont where you can hike an original portion of the Mohican-Mohawk Trail blazed by Native Americans.  This is where some of New England’s tallest and oldest trees thrive: white pines and hemlocks that have stood the test of time for over 500 years.

Lenox detour 

Driving south through a series of towns, stop at the Lenox, in the heart of the Berkshires –whose roster of past and present residents reads like a record of society’s upper echelon. Take a tour of the Mount, the spectacular mansion of renowned author, Edith Wharton. Or head to Tanglewood music venue where you can catch an awe-inspiring open-air performance from the Boston Symphony Orchestra in the summer.

Cape Cod National Seashore

Stroll through the pristine sandy beaches of the Cape Cod National Seashore

Get a taste of this Gilded Age - tour Newport’s most historic mansions

Get a taste of this Gilded Age – tour Newport’s most historic mansions

Newport pit stop 

From the mountains to the coast, you’ll cruise east until you reach the city of Newport in Rhode Island. Nestled on Aquidneck Island off Narragansett Bay, this vibrant city was once the summer home of America’s wealthiest families who, in the 1800s and early 1900s, built grandiose mansions, many of which are now museums. To get a taste of this Gilded Age, it’s off to tour Newport’s most historic mansions, including The Breakers, a Renaissance-style home built in 1895 for the Vanderbilt family.

Cape Cod 

Heading further east until you reach Cape Cod, a hook-shaped peninsula on the Atlantic Ocean. Here, you’ll find yourself surrounded by seabirds and sand dunes, quaint cottages and historic lighthouses and where life seems to move at a slower pace. There is the seaport town of Provincetown with great restaurants and quirky art galleries, or Hyannis with a fascinating harbour, where artists sell their wares in summer along the boardwalk.  Or head to Cape Cod National Seashore, an area stretching for miles and miles and take one of 11 self-guided nature trails along rugged sand dunes, scenic bike trails and the seemingly endless seashore.

Plymouth en route back to Boston 

Half way between Cape Cod and Boston is Plymouth, the quintessential New England destination where, in 1620, the Pilgrims arrived on the Mayflower and proceeded to build a community that was the seed of the USA as we know it today. Leading up to 2020, the Plymouth 400 Anniversary will hold Signature Events and Programs honouring the cultural contributions and legacies that began with the Wampanoag people and the Pilgrims, including the first Harvest Feast, acknowledged as the origin of Thanksgiving. It seems a perfect place for a final stop before heading back into Boston where the tour ends.

Turn this road trip into your own tailor made New England experience!

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