Highlights of New England’s Fall Foliage Season

By: Maxine Sheppard

September 27, 2011

For a few precious weeks every year, New England explodes into a kaleidoscope of colour. The air is crisp, harvest is underway and orchards and farmers’ markets are overflowing with ripe fruit. So when is the best time to visit? For the more northern states of Maine, Vermont and New Hampshire, peak viewing season is typically around early-to-mid October. Further to the south, Rhode Island, Massachusetts and Connecticut see their leaves turn later, with colour often lasting to November. Kicking things off in Boston, we’ve picked just a handful of highlights for a fabulous fall adventure…



Any self-respecting tour of New England should start or end in Boston. When Halloween fever takes hold, one of the best places to take a stroll is through the narrow streets of Beacon Hill, past tall red-brick townhouses adorned with refined displays of pumpkin paraphenalia. Previously home to many literary and political heavyweights including Louisa May Alcott, Robert Frost, Sylvia Plath, Edward Kennedy and John Kerry, it’s the city’s most desirable and affluent neighbourhood.



Acorn Street, Boston by darronschall on Flickr

Acorn Street, Boston by darronschall on Flickr



The Berkshires, Massachusetts

Not only do western Massachusett’s rolling Berkshire hills offer a bucolic landscape that fulfils the rural New England fantasy of every visitor, they combine this with a cluster of small towns who punch way above their weight in terms of cultural and intellectual pursuits.


Highlights include Tanglewood at Lenox, summer home of the Boston Symphony Orchestra; the Norman Rockwell Museum in the quintessential New England town of Stockbridge; progressive and arty Great Barrington which has its own currency, and lofty Williamstown, home to the Clark Art Institute and elite Williams College, consistently ranked as the best liberal arts school in the USA.


White Mountains, New Hampshire

As New England’s most significant mountain range, the White Mountains are technically part of the Appalachians and cover about a quarter of the state of New Hampshire, extending into western Maine. The major highlight for motoring foliage-seekers is the Kancamagus Highway, an outrageously scenic drive that crosses the Kancamagus Pass into the skiing and kayaking hotspots of North Conway and Jackson.



Swift River, White Mountains National Forest, New Hampshire by sskennel on Flickr

Swift River, White Mountains National Forest, New Hampshire by sskennel on Flickr



Newport, Rhode Island

Once the home of the America’s Cup race, Newport is still utterly obsessed with yachting but beyond the waterfront lies an elegant town full of renovated buildings, white-spired churches, clapboard B&Bs and a particularly grandiose millionaire’s row. Bellevue Avenue is where America’s wealthiest families built their wildly extravagant “summer cottages” during the Colonial and Victorian periods through to the Gilded Age, and during the autumn months their mature gardens are at their most golden and lovely.



Mansions along the Cliff Walk, Newport, Rhode Island by Elyssa Conley at

Mansions along the Cliff Walk, Newport, Rhode Island by Elyssa Conley at



Sleeping Giant State Park, Connecticut

For a spectacular fall foliage experience that’s well off the tourist track, head for the 30 miles of hiking trails in Connecticut’s Sleeping Giant State Park about 11 miles north of New Haven. A two-mile long stretch of rocky mountaintop resembling a large supine giant gives the park its name. A unique microclimate creates unusual thermals in warmer weather; keen birders should be sure to pack binoculars as it’s not uncommon to spot red-tailed hawks and turkey vultures trying to catch one. White-tailed deer, red foxes, chipmunks and raccoons also make a home here.



Sleeping Giant State Park, Connecticut by citizenswaine on Flickr

Sleeping Giant State Park, Connecticut by citizenswaine on Flickr



Woodstock, Vermont

Not to be confused with its hippie namesake in upstate New York, Woodstock, Vermont is an extremely well-off and well-to-do town in Windsor County (it’s the county town, no less) named by National Geographic as ‘One of America’s Most Picturesque Villages’ and one of the Top 25 Foliage Towns by Yankee Magazine. Despite its rarefied air, rural traditions remain””the surrounding farmland is dotted with classic New England red barns””and nearby Billings Farm and Museum offers a taste of Vermont-style living throughout October with pumpkin and apple celebrations, wagon rides, a harvest weekend and barn dance.




Acadia National Park, Maine

Much further north on the coast of Maine, occupying most of Mount Desert Island, is Acadia National Park – the only US National Park in New England. There’s a lot of ground to cover here, and the leaf-peeping opportunities are both remarkable and extensive. One of the best ways to orient yourself is with a drive along the Park Loop Road, a 27 mile route which connects the park’s forests, mountains, lakes and rocky coast. Best foliage viewpoints are at Otter Cliffs, which are topped with densely-packed spruce trees, and Cadillac Mountain, the oft-quoted highest peak on the Atlantic coast between Canada and Brazil.



Sand Beach, Acadia National Park, Main by Lee Coursey on

Sand Beach, Acadia National Park, Maine by Lee Coursey on


Virgin Atlantic operates a daily flight to Boston from London Heathrow airport. You can also visit Virgin Holidays for an extensive range of New England holidays and tours.

Thanks to Flickr photographer banspy for the great header shot of the Mohawk Trail at Greenfield, Massachusetts.


Maxine Sheppard

Maxine is the co-editor of the Virgin Atlantic blog. Travel and music are her joint first loves, and despite having written for Virgin for more years than she cares to remember she still loves nothing more than jumping on a plane in search of new sights and new sounds.

Categories: Our Places