Skip to content
Please select your location:
White Mountains region, Vermont

Touring New England in fall

White Mountains region, Vermont

By Audley specialist Alice

Autumn falls across New England like a bright patchwork quilt, the cooler weather painting the landscape in broad strokes of scarlet, gold and shocking orange. Locals break out their wool sweaters as the air turns crisp and the summer-blue sky deepens into cobalt.

When I visit New England for the fall foliage, I like to take a wide, lazy loop, pausing to explore an area for a few nights before setting out on another scenic drive. It helps that the region is fairly compact (for the USA) and that there’s much to see along the way — the rugged White and Green mountains, clapboard houses, tiny antique shops and white-spired churches on small town greens.

Self-driving through New England

New England road in fall
New England road in fall

The best way to tour New England in fall is in a car. In fact, the stretches between destinations are often the most memorable part of my trips. I like to take my time, idling along back roads and pausing at the many lookouts and viewpoints along the scenic routes that interlace the region. But even the verges along highways are ablaze with red sugar maples, purple ash trees and silver birches with leaves that look gilded by the sun.

This tried-and-tested route that takes me through the ever-changing landscape over the course of two weeks, with lots of time for pauses at small towns. I prefer this order because it lets me catch the peak foliage several times, regardless of the timing of that particular season.

The Maine coast

Though the highway is faster, following the irregular New England coast up from Boston to Maine offers more chance to enjoy the scenery — vibrant foliage on one side and beaches on the other. The Essex Coastal Scenic Byway and the Coastal Byway (signed as Route 1) both wind slowly through dozens of shore towns, including old fishing ports like Gloucester and Salem (of witch-trials notoriety) up to Kennebunkport.

Eastern Point Lighthouse, Gloucester, Massachusetts
Eastern Point Lighthouse, Gloucester, Massachusetts

Things to see and do in Maine

Filled with grey clapboard houses, upscale galleries and cafés, Kennebunkport has been a beach retreat for New England’s elite for generations, including the presidential Bush family.

I like to stroll along Colony Beach to enjoy the sea breezes in the evening while eating a lobster roll from nearby Mabel’s Lobster Claw. (Despite a reputation as summery fare, lobsters are actually best in the cooler months when their flesh is sweeter and firmer.) Slightly to the east, a turn along Parson’s Way takes you past the cliffs of Cape Arundel to clear views of the slate-grey waves crashing on the rocky shore, white spume shooting up from the sea clefts.

Acadia National Park
Acadia National Park

If I’m in the mood for something more active, I drive farther up the coast to Bar Harbor and Acadia National Park, both located on Mount Desert Island. Hiking through the park’s woodlands affords a chance to see the trees up close and hear the fallen leaves crunch under your boots. You might see a humpback off the coast or a lanky moose ambling along through the forest.

Last time I visited Bar Harbor, I took a tour on the lobster boat Lulu. John Nicolai, a local lobsterman, narrated the cruise in the clipped rhythms of the region. He provided a glimpse into the centuries-old art and science of catching these highly prized crustaceans as well as the history of coastal Maine. From the boat, you also have an ocean-side view of the blazing scarlet and glowing gold trees that cover the island.

If you take the most direct route, it’s about 160 km (100 miles) from Kennebunkport to Mount Washington in the White Mountains, and twice that from Bar Harbor.

The White Mountains, New Hampshire

Straddling the New Hampshire and Maine state line, the White Mountains are filled with rugged granite cliffs, clear mountain lakes and vast protected forests of oaks, pine, ash and maples.

Whether you’re gazing down from the mountains’ peaks or looking up at their forested slopes, the views here are an endless panorama of bright trees on steep slopes. Those same views also bring coach loads of leaf peepers, visitors who come from as nearby as New York City and as far away as Australia to see the annual show. They tend to congregate around the town of North Conway, so I like to base my visit out of Jackson, a tiny village that’s best known for its barn-red covered bridge.

White Mountains,  New Hampshire
White Mountains, New Hampshire

What to do and see in the White Mountains

For simply cruising along in a car and admiring the scenery, I take the Kancamagus Highway, which runs from east to west across the park. I think it offers the region’s best scenic stops, overlooking gorges, silvery waterfalls and valleys awash in drifts of crimson, ochre and bright yellow.

A literal highpoint is Mount Washington, New England’s tallest peak, which boasts incomparable views as well as the dubious distinction of having the ‘worst weather in the world’. While the claim is debatable, there’s no doubt that the mountain has erratic and extreme weather, including frigid and frequent gale-force winds. I strongly suggest that you bring layers, as well as a hat and gloves, if you decide to go up, even if the weather is balmy at the base.

The extraordinary weather means that hiking Mount Washington is a serious undertaking — even driving up can be tricky. Instead, you can take Mount Washington Cog Railway up to the peak. The three-hour round trip is narrated by the ‘brakemen’ who operate the slow-but-steady train. The steam engine is helped on its way by a cog in the rail bed to keep the train from slipping back down the steep slope. At the top, there’s enough time for a tour of the mountain’s weather observatory or simply to gaze out at the panoramic view.

When I want to hike through the White Mountains, I head for Franconia Notch State Park. At just 2.5 km (1.5 miles), Artist’s Bluff Trail offers a fairly gentle path through the woods that rewards you with views of Cannon Mountain reflected in the still surface of Echo Lake. Keep an eye out for shy red squirrels and darting chipmunks gorging themselves on fall acorns and pine nuts before the winter sets in.

The route from Jackson, New Hampshire, to Woodstock, Vermont, is about 160 km (100 miles) if you drive on the Kancamagus Highway through the National Forest.

Where to stay in the White Mountains

The Wentworth Inn is a restored Victorian hotel tucked into the heart of the village of Jackson. A convenient base for exploring the White Mountains, it’s close enough to the central town for you to be able to walk out for dinner in the evening.

The Green Mountains, Vermont

This time of year the Green Mountains belie their name and transform into a tapestry of russet, red, orange and yellow. Though there’s good hiking here, I prefer to spend my time driving along narrow country lanes to take in the many postcard-pretty towns and farm fields mellowing under the warm October sun. There are dozens of them, one around every corner it seems, each populated by rambling farmhouses or Colonial mansions, gnarled apple trees and carved pumpkins perched on stone walls. But a few are worthy of special attention.

Green Hills, Vermont
Green Hills, Vermont

What to do and see in Vermont

A storybook version of a New England village, Woodstock has been an enclave for the wealthy since the 1700s. Its oval town green is surrounded by solemn red-brick town buildings and Federal mansions with wide porches and black shutters, all carefully preserved. The Ottauquechee River runs through town and is spanned by three different covered bridges.

An hour to the southwest, the village of Manchester is tucked into the shadow of Equinox Mountain. If you’re feeling energetic, there’s hiking on the mountain and excellent trout fishing in the nearby Batten Kill River. In nearby Quechee, the Simon Pearce Restaurant offers locally sourced food next to a workshop where you can watch local glassblowers practise their art.

The Vermont Country Store is an old-fashioned general store that offers a whole selection of goods, from writing desks to modest nightgowns to kitchen wax to ribbon candy. Though it sells primarily through mail-order, there are several brick-and-mortar locations in the state.

It’s about 120 km (75 miles) from Manchester to Stockbridge, Massachusetts. From Woodstock, the drive is doubled.

Where to stay in Vermont

Outside Manchester, The Inn at Ormsby Hill is set in a white farmhouse. It’s a peaceful retreat if you want to read a book on the back deck and admire the rolling hills.

The conservatory dining room, The Inn at Ormsby Hill, Manchester Village
Inn at Ormsby Hill

The Berkshires

As they head south into Massachusetts, the Green Mountains lose some of their lofty majesty and settle into being the Berkshires. The slopes here are somewhat gentler, though there are still some steep inclines and impressive summits. The wealth of cultural attractions more than makes up for the less-dramatic landscape, however, and this far south the leaves retain their vivid hues later into the season.

Village in the Berkshires
Village in the Berkshires

Things to do and see in the Berkshires

Of the Berkshires’ dozens of museums and other cultural institutions, I’m particularly fond of the Norman Rockwell Museum, which celebrates the life and work of the local artist who made his name illustrating the covers of The Saturday Evening Post. Rockwell’s wry aesthetic visually defined New England, and indeed America, during the middle part of the 20th century.

The museum is located in Stockbridge, which is an excellent central base in the Berkshires. The village is also home to the Red Lion Inn, one of the country’s oldest hostelries. The front porch of the inn is often decorated with carved pumpkins and I like to pause there on a chilly afternoon for a mug of mulled cider.

Stockbridge to Chatham is about 320 km (200 miles), if you stick to the major highways.

Cape Cod

At the opposite end of the state from the Berkshires, Cape Cod stretches like a flexed arm into the Atlantic. By mid-October, the cool fall winds have whisked away the last of the summer tourists and left the beaches nearly deserted for long walks. The once-bustling shore towns turn sleepy, basking in the autumnal sun, providing a quiet setting for the last few days of your trip.

Humpback whale, Cape Cod
Humpback whale, Cape Cod

What to see and do on the Cape

Thanks to its underwater geography, the ocean off Cape Cod provides some of the best whale watching in the world and their migration patterns take humpbacks right past here in the autumn. I’m fascinated by whales, personally, and it’s hard to describe the primal pleasure of seeing such an enormous animal in its natural habitat. The sleek grey giants breech and frolic in the vast ocean, seemingly unaware of the tiny humans nearby.

Most of the whale watch cruises take half a day and leave from Provincetown, the eccentric town at the very tip of the Cape. Though there’s never a guarantee that you’ll see a whale, the captains are very good at finding the huge animals.

Whales are more active in the afternoon, so I spend the morning exploring the streets of Provincetown, sometimes called ‘P-Town’, and enjoy a leisurely lunch at one of the many cafés there. When I return to shore with my hair in a salty wind-blown tangle, I like to indulge in one last lobster roll at the Lobster Pot on Commercial Street.

Where to stay on the Cape

The Platinum Pebble in West Harwich blends the exceptional service and intimacy of a B&B with the convenience of hotel amenities, including a pool. It’s just a short walk to either the beach or into town.

Platinum Pebble Inn The Lounge
Platinum Pebble

Best time to see fall foliage in New England

The precise date of peak foliage is a hotly debated topic in New England and, if you ask five locals, you’re likely to get ten opinions. In general, however, leaves start to turn in the north at the start of October and the change sweeps slowly south, moving faster in the higher elevations, for two or three weeks. If you drive in a wide loop through the region, you’re likely to pass through the most dazzling displays several times.

I prefer to err on the early side because pre-peak foliage is still remarkable, and if you wait too long you’ll be caught in the autumnal rains.

Fall festivals in New England

Columbus Day is celebrated on the second Monday of October, and the long weekend is a popular time for locals to enjoy the leaves. The driving can be difficult as leaf peepers flock to the area in droves, clogging up scenic highways and rural roads. Instead, I suggest settling into an inn to explore locally for those three days.

Start planning your self-drive itinerary to New England

Start thinking about your experience. These itineraries are simply suggestions for how you could enjoy some of the same experiences as our specialists. They're just for inspiration, because your trip will be created around your particular tastes.

View All Tours in New England