How to plan the ultimate road trip through New England

In many of the stories about the origin of the United States, one place recurs: New England, the northeastern region comprising the states of Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island and Vermont. This land was, of course, inhabited long before the Europeans arrived and claimed it as their own. Experts estimate there were between 70,000 and 100,000 Native Americans living here at the beginning of the 17th century, when the first English settlers arrived in modern-day Plymouth, Massachusetts. The events that took place in the centuries that followed, from the founding of English colonies to the American War of Independence, would forever change the course of history.

New England’s red-brick cities and heritage sites are welcoming harbours for history- and culture-lovers — but the region offers much more. There are the White Mountains, a rugged sub-range of the Appalachians; foggy islands and Atlantic capes that make for coastal road trips to rival anywhere in North America; and everything in between. Much of it is empty and wild, the atmosphere only enhanced by thriving populations of whale, black bear and bobcat. The hardest part about visiting might be deciding what to miss out, with the combined states almost the same size as Great Britain.

No matter where you go, you’ll find all roads lead to Boston, the capital of Massachusetts and, arguably, of the wider region. Even though it’s been 250 years since British tea chests were flung into its harbour — a key act of rebellion in the lead-up to American independence — visiting its Federal-style row houses still feels like stepping into a history book. Head to nearby Cape Cod and Nantucket for walks on long stretches of beach and to try Atlantic catches — no itinerary is complete without stops at oyster houses and lobster shacks.

Tack on more time for Rhode Island and Connecticut, the lesser-visited coastal states to Massachusetts’s south, to learn about different chapters in the region’s history, including its Indigenous cultures and Gilded Age splendour of the late 19th century. To the north, New England stretches out its limbs. Vermont and New Hampshire are a free-flowing wilderness of green hills, maple farms and country stores. They’re especially scenic in autumn — New England is the world’s unofficial leaf-peeping capital — and offer great adventures in winter, when they transform into skiing resorts. Slipping further north, Maine’s whole tourism pitch is modelled on getting outdoors. It’s a state for moose safaris, camping weekends and shore excursions on lobster boats — the New England of the mind’s eye.

Itinerary 1: Coastal New England

Start point: Mystic, Connecticut
End point: Acadia National Park, Maine
Distance travelled: 520 miles
Average length: 10 days

Four hundred years is a long time to have gone fishing — and it shows. For centuries, New England’s triumph has been the connection between its land and sea, with its maritime trades and communities prospering since Plymouth was settled by the English in 1620. Today, the region makes for an extraordinary coastal road trip. There are port towns snagged with boats, nets and anchors; hook-shaped peninsulas frequented by whales; and show-stopping lighthouses popping up around every other corner.

This trip begins with a dose of culture in the town of Mystic. Continue to Newport, the summer resort favoured by America’s Gilded Age elite, before moving on to big-hitting Massachusetts. This itinerary spotlights the Cape Cod peninsula and its island of Nantucket, which best encapsulate the state’s coastal way of life, but do consider spending time in the local capital of Boston if you haven’t visited already.

Half a day’s car ride north from Massachusetts, the laid-back town of Kennebunkport in Maine still provides lobster the way it’s supposed to be enjoyed — right from the trap. The wild Acadia National Park, encircled by gurgling ocean, is journey’s end on this itinerary.

1. Mystic, Connecticut
The pretty town of Mystic is home to the Mystic Seaport Museum, the nation’s leading maritime centre. For a different perspective on the US’s seafaring history, don’t miss Entwined: Freedom, Sovereignty and the Sea, an exhibition on maritime artefacts from Indigenous and African communities, on view until spring 2026. Or detour for the Mashantucket Pequot Museum and Research Center: a 20-minute drive north of town, the tribally owned, 308,000sq ft complex explores the cultures of Native Americans in the region.

2. Newport, Rhode Island
An hour’s drive to the east is America’s ‘City by the Sea’. Newport has been a popular summer resort since the Gilded Age, when the country’s elite came to vacation in their waterfront ‘cottages’, now more appropriately known as the Mansions. Of the 11 that are open for visits, the grandest is The Breakers. It was built by socialite Cornelius Vanderbilt II, but with its 70 rooms, Italian Renaissance style and breathtaking chandeliers, it could very well be fit for royalty.

3. Nantucket, Massachusetts
From Newport, it’s a 45-minute drive to New Bedford, where you can board the two-hour ferry to the Cape Cod islands. Tourism has been flourishing here for decades, especially on Martha’s Vineyard. Nantucket is much quieter, though. From here, you can sail on with a charter to the smaller islands of Muskeget or Tuckernuck. Or head to Nantucket’s Jetties Beach to catch a sunset overlooked by a lighthouse as stripy as a prep school tie. Bed down in one of the captains’ houses turned cottages.

4. Cape Cod, Massachusetts
Leaving Nantucket, it’s another two-hour ferry to mainland Cape Cod, the fishing hook-shaped peninsula that’s as romantic and windblown as New England gets. It only takes around 90 minutes to drive but merits much more time. The fishing community of Chatham has clapboard houses, picket fences and crab cakes. An eco-cruise from Harwich Port takes you to sand spits populated by grey seal pods. The Cape Cod National Seashore, meanwhile, is 30 miles of umbrella-free beaches. Journey’s end brings travellers to Provincetown, one of America’s great LGBTQ+ destinations, with bars, carnival colour and burlesque clubs.

5. Kennebunkport, Maine
A four-hour drive north, Kennebunkport is often introduced as Maine’s prettiest town. It deserves that billing, with mansion houses, fetching docks and streets with antique stores and old-time sweet shops. It’s a slow sort of place; if you want more excitement, tag on an extra day and head to Portland, the state capital 40 minutes to the north.

6. Acadia National park, Maine
The classic New England coastal scene, familiar from a million photographs, might just be of this national park on Mount Desert Island, with several ocean-bracing nooks.

Base yourself in Bar Harbor, a three-hour drive from Kennebunkport and the main jumping-off point to discover this 47,000-acre landscape. The quirks of the topography here give rise to granite cliffs topped by lighthouses, silvery lakes to cannonball into and countryside ideal for hiking and camping. Sunrise on Cadillac Mountain, the highest point on the region’s Atlantic coast, is not to be missed.

Itinerary 2: Cultural New England

Start point: Hartford, Connecticut
End point: Bangor, Maine
Distance travelled: 465 miles
Average length: 10 days

New England is such a cultural heavyweight, its stories flow in the veins of most Americans. This itinerary uses some of the destination’s pivotal historical moments and famous residents to guide a trip from Connecticut to Maine — and from the 17th century to the present day. Rent a car and give yourself plenty of time on the road, to experience the sense of discovery that much local history instils.

Start in Hartford, famed for its literary heritage, before moving onto Boston to follow in the footsteps of the nation’s founders. Salem, with its history of witch trials, and Concord, the site of key 18th-century battles, make for interesting day trips before the route heads north through New Hampshire.

Home to Mount Washington, New England’s highest peak at 6,288ft, the White Mountains are the best place to swap the wheel for walking boots. In Maine, the road skirts the Great North Woods to Bangor, the longtime home of author Stephen King, for the last stop.

1. Hartford, Connecticut
This city by the Connecticut River brings to mind the sound of pages turning and of coffee being sipped. It has a gloriously gothic State Capitol building, but come to pay homage to two 19th-century literary greats. Visit the Mark Twain House & Museum, the Victorian family home of the author of The Adventures of Tom Sawyer and The Adventures of Huckleberry Finn, then it’s a two-minute walk to the Harriet Beecher Stowe Center. A tour here explores the life of the abolitionist author of Uncle Tom’s Cabin — as well as social issues including enslavement and racism.

2. Boston, Massachusetts
It’s a two-hour drive to New England’s biggest hitting city. Boston labours hard over its history and a key highlight is the Freedom Trail. It winds past a roster of revolutionary landmarks, including Boston Common, the country’s oldest public park; Faneuil Hall, where speeches encouraging independence from Great Britain took place in the 18th century; and the site where Benjamin Franklin went to school. An equally memorable education is to experience the thwack of a baseball at Fenway Park, home of the Red Sox. Locals call it the definitive sports night in America.

3. Salem, Massachusetts
Take a day trip to Salem, a half-hour drive east of Boston. The town’s most infamous period came between February 1692 and May 1693, when 200 locals were accused of the dark arts and persecuted — the largest series of witchcraft trials to ever take place in North America. Eventually, 19 were hanged. Join a tour to see the Witch House, where one of the judges lived, the Witch Trials Memorial and the Old Burying Point Cemetery.

4. Concord, Massachusetts
Literary enthusiasts will find more highlights a half-hour drive west of Boston. This town has the former homes of Louisa May Alcott, who wrote Little Women, and Nathaniel Hawthorne, author of The Scarlet Letter. But the main attraction is arguably Minute Man National Historical Park, where the battles of Lexington and Concord marked the start of the American War of Independence.

5. Bretton Woods, New Hampshire
The horizon widens on the two-hour drive north to the White Mountains. Base yourself in Bretton Woods to discover this thickly forested territory, which has sections of the 2,200-mile Appalachian Trail. Or head to Mount Washington: in 1934, its observatory noted the highest wind speed ever recorded by man.

6. Bangor, Maine
Finish with a three-hour drive to this town, whose reputation was built on horror. Derry, the fictional setting of Stephen King’s Carrie, Pet Sematary and It, is based on Bangor, the author’s hometown. But such weight hangs lightly on its streets; visit Stephen King’s mansion, then the diners and bookstores he still frequents.