Uncover New England: History. Homes. Happenings.

Uncover New England: History. Homes. Happenings. | September 2026

As fall arrives in New England, the region takes on a new rhythm — crisp mornings, brilliant foliage, harvest traditions, and a renewed energy across its towns, cities, and coastlines. It’s a season that captures so much of what makes this place special: historic architecture and walkable villages, vibrant cultural and culinary traditions, access to nature, and communities that continue to evolve while honoring their past.

In Boston, the transformation of the Central Artery into the Rose Kennedy Greenway is a striking example of that evolution — reconnecting neighborhoods and the waterfront while creating new spaces to gather and enjoy the city.

In this edition, we explore some of the places, stories, and experiences including Boston's Head of the Charles Regatta, that make New England such a rewarding place to live and visit, along with distinctive homes and real estate opportunities that reflect its enduring appeal. Join me as we take a look at the character, history, and lifestyle that make this region especially inviting in the fall.

The Big Dig: How Boston Reclaimed Its Center

September 1991 - November 2007

The Rose Kennedy Greenway from the North End to Chinatown

Central Artery, 1991 (Above Left) | Map of Rose Kennedy Greenway, Present (Above Right)

For much of the second half of the 20th century, an elevated highway cut directly through the heart of Boston.

The Central Artery opened in 1959, carrying traffic along an elevated six-lane roadway through downtown. It was intended to relieve congestion, but Boston grew rapidly around it. By the early 1990s, the highway was carrying more than 200,000 vehicles a day, nearly three times the volume it had been designed to accommodate. Perhaps the most interesting legacy of the Big Dig is what didn't get built.

Once the elevated highway was removed, Boston had an extraordinary opportunity: approximately 27 acres running through the center of downtown suddenly became available for something other than traffic.

Instead of replacing the highway with another massive piece of infrastructure, much of the corridor became public open space. That became the Rose Fitzgerald Kennedy Greenway.

Today, the Greenway is a 1.5-mile, 17-acre linear park stretching from Chinatown through the Financial District and Wharf District to the North End. Nearly 900 trees line its boulevard, along with gardens, lawns, fountains, public art, walkways and gathering spaces.

The transformation is remarkable: the same corridor that once divided Boston now helps connect it. The project allowed Boston to retain its historic neighborhoods—including the North End and waterfront—while dramatically improving transportation and creating new public spaces.

Fall in New England

A Season Worth Coming Home For

There is a reason people plan special trips to New England each fall. For a few extraordinary weeks, the region takes on a remarkable beauty — forests glow with brilliant color, mornings turn crisp and clear, and historic towns, country roads and coastal communities seem to slow into a more peaceful rhythm. From the Berkshires and western Massachusetts to New Hampshire’s White Mountains and the rugged coast of Maine, each landscape offers its own expression of the season.

But fall in New England is about more than the foliage. It is a time for apple orchards and farm stands, scenic drives and hikes, long lunches, cultural discoveries and quiet walks through historic villages.

Perhaps that is why autumn feels so special here. It offers a glimpse of a way of life that is connected to nature, community, history and the changing seasons — a place where the landscape becomes part of everyday life, and where there is always another road, town or shoreline to discover.

One of the most highly anticipated events of the fall season is The Head of the Charles Regatta. More than simply a rowing event, it captures something very Boston/New England: sport, tradition, collegiate culture and the Charles River landscape all at once.

Imagine stepping out of your home in Cambridge, Beacon Hill, Brookline or Newton and having one of the country's great sporting traditions happening practically outside your door. It’s one of the many ways that living in Boston connects you to a vibrant community, rich traditions, and experiences that become part of everyday life.

A Reputation Built on Trust, One Exceptional Property at a Time

Notable Listings | On Market

From a private, resort-like retreat just minutes from Boston to a contemporary beachfront home on the New Hampshire coast, these two properties offer very different ways to experience New England living. In Weston, expansive grounds, a pool, tennis court and beautifully designed spaces create an exceptional setting for everyday life, entertaining and time spent at home. In Seabrook, a spacious modern residence sits directly on the beach, offering the ease of year-round living or the perfect gathering place for family and friends throughout the summer.

With a reach that extends from Berkshire County and the Pioneer Valley through Rhode Island and Boston’s western suburbs, and north through New Hampshire to Maine, we have the perspective, relationships and local expertise to skillfully guide clients across a remarkably broad and diverse New England landscape.