Maserati GranTurismo Tour: Boston to NY in Search of the Old Post Road

2012 Maserati Gran Turismo

In the early days there was the Pequot Trail, the Nashaway road and the Mohawk trail: paths traced by the passage of Native American tribes of the Northeast on their migration routes. These were faltering and fragmented trails which Mother Nature and the elements could modify at their pleasure. Then came the European settlers, whose arrival ushered in the need to establish reliable, safe communications between the newly founded cities of Boston and New York. In January 1673 the governor of New York, Francis Lovelace, appointed a horseback mail carrier to ride all the way to Boston, braving a perilous, two-week long journey. Thirty years later, the route had already become an established post road. This marked the beginning of the Boston Post Road, America’s first true “Main Street”. The road, barely wide enough to accommodate two passing horses, and its prolongation to Philadelphia and Virginia, soon started to spread the settlers’ malcontent for the English crown, then letters from one conspirator to another; later still, it carried convoys of troops bearing the new stars-and-stripes flag. In short, this road witnessed the birth of an entire nation that was to make mobility one of the cornerstones of its development.


We have come in search of the relics of the old Boston Post Road on a mid-autumn morning in the heart of Indian Summer, when dwindling daylight hours prompt the chlorophyll to gradually retreat from the leaves, as sugar and toxins decay rapidly, changing the shade of leaves to an Impressionist colour palette: red for oaks, golden yellow for poplars, orange-red for maples. To offset this trip down memory lane of America’s earliest roads, we’re travelling in a Maserati GranTurismo, a triumph of the modernity of contemporary transport and a prime example of Italian technology and creative genius. In our lavish leather lounge with 440 horsepower under the bonnet, we’re following the trail of the old post stagecoaches.

We know that the road began – or ended, depending on the direction you travelled – at the old Town Hall in Boston. No visible sign of the old post office remains today at the corner of Washington and State Street. And yet an important piece of history began right at this intersection.

2012 Maserati Gran Turismo

We travel through the narrow streets of Beacon Hill, the city’s old aristocratic neighbourhood, searching in vain for signs of the old road. We have to leave the centre to reach the southern district of Roxbury and finally set our eyes on the first jewel of our journey. On an anonymous street corner of this student suburb, in front of a red brick building that houses an auto-repair workshop, is the dark silhouette of the cornerstone that once marked the central point between the southern road and the westbound road to Springfield. The date engraved on it reads 1744.

We leave Boston westbound on the I-90 and then we take the I-20. We immediately find ourselves in dense woods. It’s only natural to think back to the story of Sarah Kemble Knight, the first woman to write a travel journal of the five-month round-trip she made in the winter of 1704 following the postal routes. She complained of 3a.m. rises, river crossings aboard precarious canoes and quite a bumpy ride.

Along the way we encounter road sign with the name Old Post Road. But even more exciting is the hunt for the surviving milestone markers. Benjamin Franklin became Postmaster General in 1753 and immediately undertook inspection and survey of the main routes: his aim was to improve the network. It was Franklin who ordered the installation of milestones, commonly referred to as Franklinstones, which neglect, time and a flourishing private collectors’ market have today reduced to around thirty remaining specimens scattered over a 350 kilometre route.


Between the twelfth and thirteenth mile, an essential stop-off is the Wayside Inn, a tourist attraction which Henry Ford had rebuilt in the twenties on the site of the former Red Horse, or Howe’s Tavern, as it was known, after the original owner. It is America’s oldest inn, the only one which, under various architectural guises, has been in business since 1702, although only a tiny remnant uncovered between plasterboard panels today allows a glimpse of the smoke-blackened surface of the original wooden beams. Ford, who had a keen interest in history and Americana in particular, turned the property into the perfect postcard image of New England, complete with a general store and a fully working water mill for grinding corn. However, the old bar of the inn, which originally opened to serve “travellers, their horses and cattle” is really authentic and reminiscent of memories and tales, like those told by poet Longfellow, who here penned “Tales from the Wayside Inn”.

Of the other dozens of inns and taverns once dotted along the road (stagecoach horses were changed every 35 kilometres), none still operate today. Their signs have survived, housed in Hartford city museum in Connecticut, and there are a few urban relics of old houses, protected by local historical bodies as historic landmarks, in the villages of Darien, Connecticut and Rye, New York. In any case, the road makes for an inspiring journey, made all the more romantic by the autumnal sky and variegated foliage that accompanies us all the way to New York.

Amid the narrow, permanently shaded canyons between skyscrapers, you can still find little gems like Fraunces Tavern, which witnessed rowdy meetings of freemason groups in pre-revolutionary times. It’s pointless to search for marker “number zero” which was installed at the intersection of Bowery and Canal Street, today dominated by the monumental Manhattan Bridge archway. In its place, however, is the last surprise on our journey, perfect in its absolute gratuitousness: by some twist of fate, where the milestone once stood, now there is a bus stop of a Chinatown bus operator, Fung Wah Bus Transportation Inc.

How convenient.


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