New England in the fall: From Boston to New York
When to go
Late September to late October, and the leaves turn from north to south and from the mountains down to the sea. In northern Vermont and the high White Mountains the colour peaks around the end of September and the first days of October; in the valleys of New Hampshire in the first half of October; on the coast of Maine and around Boston in the second half. Columbus Day weekend, the second Monday of October, is the busiest of the year on the Kancamagus. Nights in the mountains drop to freezing, and the Mount Washington Auto Road closes for the winter in late October.
The stops
Interactive map of the route on our site ›
- Boston2 nights
Boston Common, set aside in 1634, is the oldest public park in the United States, and from it the Freedom Trail, a red line in the pavement, leads some four kilometres past sixteen sites of the Revolution. On Beacon Hill the Vilna Shul, built in 1919 by Jews from Vilnius, is the last of the city’s immigrant-era synagogues still standing, and it is open to visitors.
- Salemstop on the way
In 1692 nineteen people were hanged here as witches, and one man, Giles Corey, was pressed to death under stones for refusing to stand trial. The town also has the Peabody Essex Museum, which grew out of a society of sea captains founded in 1799 to keep what they brought home from the East.
- Portsmouth NHone night
The town was settled in 1630 as Strawbery Banke, after the wild strawberries on the riverbank, and the old waterfront quarter of that name is now a museum of some thirty houses from four centuries. In 1905 the treaty that ended the Russo-Japanese War was negotiated at the naval shipyard across the river, and it won Theodore Roosevelt the Nobel Peace Prize.
- Kennebunkportstop on the way
A shipbuilding village turned summer resort, with shops and lobster shacks around Dock Square. On Walker’s Point, out on the rocks along Ocean Avenue, stands the summer house of the Bush family, which served as the summer White House of the first President Bush.
- Portland2 nights
The Great Fire of 4 July 1866 burned much of the city, and the brick and granite warehouses of the Old Port were built after it. The poet Henry Wadsworth Longfellow was born here in 1807; and the Etz Chaim synagogue of 1921 on Congress Street, the last of the immigrant synagogues of Portland, now holds the Maine Jewish Museum.
- Portland Head Lightstop on the way
The oldest lighthouse in Maine, first lit in January 1791, on a rock in Fort Williams Park at Cape Elizabeth, a quarter of an hour from town. Longfellow used to walk out to it, and the keeper’s house is now a small museum.
- North Conway2 nights
The market town of the White Mountains, with its yellow Victorian railway station of 1874 still on the main street; the Conway Scenic Railroad runs excursion trains from it into Crawford Notch. New Hampshire has no sales tax, so the outlet stores along the road fill up on rainy days.
- Mount Washington Auto Roadstop on the way
A toll road opened in 1861 that climbs about twelve kilometres to the top of Mount Washington, 1,917 metres, the highest peak in the northeast. On 12 April 1934 the observatory on the summit measured a gust of 231 miles an hour, about 372 kilometres an hour, a world record that stood until 1996.
- Kancamagus Highwaystop on the way
Route 112 runs some 56 kilometres from Conway to Lincoln through the White Mountain National Forest, over a pass of about 870 metres, with no petrol stations, shops or houses on the way. It is named after Kancamagus, a seventeenth-century chief of the Pennacook, and in foliage season it is one of the most driven roads in New England.
- Franconia Notchstop on the way
A narrow pass between two ranges, where the interstate shrinks to a parkway. On the cliff above Profile Lake stood the Old Man of the Mountain, a granite face that is still on the state’s road signs and on its quarter of 2000; it fell on 3 May 2003, and steel profilers at the lakeside now let you see it again in line with the rock.
- Littleton NHone night
A mill town on the Ammonoosuc River with a long brick main street. Eleanor H. Porter, who wrote Pollyanna, was born here in 1868, and a bronze statue of the girl stands outside the library; on Main Street, Chutters is listed by Guinness as having the longest candy counter in the world.
- Montpelierstop on the way
The smallest state capital in the United States, with fewer than nine thousand people, and the only one without a McDonald’s. The dome of the State House is covered in gold leaf and topped by a statue of Ceres, the Roman goddess of agriculture.
- Ben & Jerry’s Waterburystop on the way
Ben Cohen and Jerry Greenfield opened their first scoop shop in 1978 in a renovated petrol station in Burlington, after a five-dollar correspondence course in ice-cream making. At the factory in Waterbury the tour ends with a tasting, and on the hill behind it the Flavor Graveyard has a headstone for every flavour they retired.
- Stowe2 nights
A village with a white steepled church under Mount Mansfield, at 1,339 metres the highest mountain in Vermont. After they fled Austria, the von Trapp family of The Sound of Music settled here in 1942, and their lodge on the hill is still run by the family, with the family graves a short walk above it.
- Burlington and Lake Champlainstop on the way
The largest city in Vermont, on the shore of Lake Champlain, with the Adirondacks of New York across the water. Bernie Sanders was its mayor from 1981 to 1989, and in 2014 it became the first city in the United States to get all its electricity from renewable sources.
- Quechee Gorgestop on the way
Vermont’s Little Grand Canyon, a gorge some fifty metres deep cut by the Ottauquechee River at the end of the last ice age. You look down into it from the bridge that carries Route 4, and a trail leads down to the water.
- Woodstock VTone night
A village of white houses around an oval green, with a covered bridge over the Ottauquechee. The first ski tow in the United States, a rope driven by the engine of a Model T Ford, ran on a farm just outside it in January 1934; and on the hill above the green, the Marsh-Billings-Rockefeller National Historical Park tells the story of conservation in America.
- Westonstop on the way
A hill village of white clapboard houses around a green. The Vermont Country Store here, opened by Vrest and Mildred Orton in 1946 and still run by their family, sells the household goods and sweets of an older America.
- Manchester VTone night
A resort town under Mount Equinox, where Charles Orvis founded his fishing-tackle company in 1856. Hildene, on the edge of town, was the summer house of Robert Todd Lincoln, the only son of Abraham Lincoln to live to adulthood, built in 1905.
- Bennington Battle Monumentstop on the way
A stone obelisk some 93 metres high, dedicated in 1891 and still the tallest structure in Vermont. It marks the supply depot that the British tried to seize in August 1777; the battle itself was fought a few kilometres away, across the border in New York.
- Clark Art Institutestop on the way
A museum in the hills of Williamstown, opened in 1955 by Sterling Clark, an heir to the Singer sewing-machine fortune, and his wife Francine. Its collection holds more than thirty paintings by Renoir.
- Stockbridge MAone night
A Berkshire village whose main street, with the Red Lion Inn, a tavern since 1773, is the one Norman Rockwell painted under snow. Rockwell lived here from 1953 until his death in 1978, and the Norman Rockwell Museum outside the village holds the largest collection of his work.
- Home of Franklin D. Rooseveltstop on the way
Springwood, the house at Hyde Park where Franklin Roosevelt was born in 1882 and where he is buried in the rose garden, beside Eleanor. Beside it stands his library, opened in 1941, the first presidential library in the United States.
- Walkway Over the Hudsonstop on the way
A railway bridge of 1889 at Poughkeepsie, about two kilometres long and some 64 metres above the Hudson. A fire in 1974 put it out of use, and in 2009 it reopened as a park for walkers and cyclists, with the whole river valley in autumn colour below it.
- Cold Spring NYone night
A village of antique shops on the Hudson, facing West Point across the river. The West Point Foundry, founded here in 1817, cast the Parrott guns of the Civil War, and its ruins lie in the woods just south of the village.
- New York2 nights
Times Square took its name in 1904, when The New York Times moved into a tower on it. On the Lower East Side the Eldridge Street Synagogue of 1887, the first great synagogue built in America by Jews from Eastern Europe, was restored and reopened as a museum in 2007.
What it costs
Eighty dollars a night is the room. The car, the fuel and the tolls are yours: the Massachusetts Turnpike, the Maine Turnpike and the bridges into New York are all tolled, mostly read electronically, and the rental company passes them on with a daily fee for its transponder. A one-way rental from Boston to New York usually carries a drop charge. The extras worth budgeting are the Mount Washington Auto Road, paid per car and driver, and parking in New York, which costs more than anywhere on the route; most people return the car as soon as they arrive.
What to know
Four things. One: right on red. After a full stop you may turn right at a red light unless a sign says no, but not in New York City, where it is forbidden everywhere unless a sign allows it; at a four-way stop, whoever stopped first goes first. Two: school buses. When a yellow school bus flashes its red lights and swings out its stop sign, every car stops, in both directions, unless a divider separates the lanes; passing it is one of the most serious offences on American roads. Three: tolls. Many toll points have no booth at all; a camera reads the E-ZPass transponder or the plate, so agree with the rental company how tolls are charged. Four: the licence. Bring your Israeli licence together with an International Driving Permit; the rental desk mostly asks for the licence and a credit card, but a police officer may want the permit. In the mountains of New Hampshire and Vermont, watch for moose on the road at dusk.
Roads, tolls and rules
The United States drives on the right. From Boston up the coast to Portland the interstate is fast; in the White Mountains and in Vermont the roads are two-lane, through valleys and over notches, and they slow to a crawl on foliage weekends. Fuel up before the Kancamagus, which has no services on the whole crossing. No day is much longer than 150 kilometres: the coast is split with a night in Portsmouth, the mountains with a night in Littleton, and the way down from Stowe to New York takes five short days, through Woodstock, Manchester and the Berkshires to the Hudson Valley.
Travel New England in the fall: From Boston to New York
The route on our site, with a room up to $80 every night.