May 16, 2026

How Main Street Hospitality Came to Own the Berkshires

The largest hotel company you may not know you know

If you've stayed in the Berkshires any time in the last twenty years, there's a reasonable chance you've stayed at a Main Street Hospitality property without realizing it. The Red Lion Inn in Stockbridge. The Williams Inn in Williamstown. The Porches Inn at MASS MoCA in North Adams. Race Brook Lodge in Sheffield. And the hotel formerly called the Briarcliff Motel, now reopened as The Little Lion.

Five hotels. One Stockbridge-based company. Five of the most-recommended Berkshires lodging options in nearly every mainstream travel write-up of the region.

Main Street Hospitality isn't a household name outside the region — most of its hotels carry their own branding and read as independent on the surface — but within Berkshires hospitality, it's the single biggest force shaping what the region looks like to visitors. Understanding how Main Street came to own the Berkshires is useful context for any travel decision in the region.

Where it started: the Red Lion Inn

The through-line of Main Street Hospitality's history is the Red Lion Inn in Stockbridge — Norman Rockwell's hometown, the Red Lion on Rockwell's Christmas postcard of Main Street, the 1773 inn that has occupied the same building (with rebuilds after an 1896 fire) for two and a half centuries.

In 1969, John "Jack" Fitzpatrick, a Pittsfield-born restaurateur, bought the Red Lion Inn. The hotel had been on a slow operational decline through the mid-20th century, and the Fitzpatricks — Jack, his wife Jane, and eventually their children — spent the 1970s and 1980s restoring and repositioning it as an anchor of Berkshires tourism.

For the Red Lion's first fifty years of Fitzpatrick ownership (1969 to roughly 2020), this was essentially a single-property operation. Jack Fitzpatrick became a significant civic figure in the Berkshires. His wife Jane was a decorative arts authority. The Red Lion became synonymous with Stockbridge.

The expansion: 2001–2015

The transition from single-property to portfolio started quietly. In 2001, the Fitzpatricks opened the Porches Inn in North Adams — effectively, a restoration of a row of 19th-century worker's housing across the street from the newly opened MASS MoCA. Porches was the first move that turned the Fitzpatrick family hotel operation into a multi-property hospitality company.

Over the next decade-and-change, the family (and the company, formally named Main Street Hospitality around this time) added:

The Williams Inn in Williamstown (acquired in 2007, rebuilt-and-reopened in 2019 as a purpose-built hotel on a new site).
Race Brook Lodge in Sheffield (added to the portfolio in the 2010s).
The Briarcliff Motel in Great Barrington, which was operated under Main Street management and has since been rebranded under a new operating structure as The Little Lion.

The pattern across these acquisitions was consistent: identify an underperforming Berkshires hotel property in a high-interest location, restore/reposition it, and integrate it into a shared back-office operation.

Why this matters to travelers

Main Street Hospitality is a perfectly legitimate hotel company, and several of its properties are genuinely excellent. The Red Lion is, in many ways, the hotel the Berkshires would lose most if any single property were to close — it is the region's anchor. The Porches is thoughtfully done. The Williams Inn rebuild is well-executed.

But a company with five properties operating under shared management is structurally different from a single-property independent. The same procurement relationships, the same staff training, the same revenue management systems apply across all five. Which is why, for our editorial purposes at lehotelist, we don't include Main Street properties on our independent-Berkshires list — they sit just over our ≤5-property threshold, and the operating model is consolidated enough that calling them "independent" in the way Stonover Farm or Tourists are independent would be misleading.

The five properties, briefly

The Red Lion Inn, Stockbridge. 125 rooms. Historic anchor. Peak-season bookings recommended 90+ days out. Strong for first-time Berkshires visitors and for multigenerational family trips. Main Street's flagship.

The Williams Inn, Williamstown. Rebuilt 2019 as a new building on a new site (the original 1953 Williams Inn was demolished). 64 rooms. Williamstown has the Clark Art Institute, Williams College, and the Williamstown Theatre Festival — worth the trip. But the rebuilt hotel has the clean-but-generic quality of many contemporary college-town hotels.

The Porches Inn, North Adams. 52 rooms across restored 19th-century row houses directly across from MASS MoCA. Of the five, this is probably our favorite for design. Tourists across town is better, but Porches is a solid MASS MoCA-focused base.

Race Brook Lodge, Sheffield. A more rustic, retreat-style property on the Connecticut border. 40 rooms plus event spaces. Popular for music events, wellness weekends, and family reunions.

The Little Lion, Great Barrington. The Briarcliff Motel's latest iteration. Mid-scale, in-town, functional.

What we recommend instead

If the Main Street operational model isn't a fit and you want genuinely independent Berkshires lodging, the short list:

Tourists in North Adams — the region's most architecturally significant hotel, 48 rooms, independent.
Stonover Farm in Lenox — three en-suite rooms plus cottages, family-run, Tanglewood-adjacent.
Doctor Sax House in Lenox — nine rooms in a restored speakeasy, run by Kelly and Bryan Binder.
Birchwood Inn and Rookwood Inn in Lenox — sister properties, same owners (Seth Johnson and Russell Lange), also family-run, two-hotel operation.
Granville House in Great Barrington — five rooms, Michelin Key, ex-New York restaurant people.
Mezze Guesthouse in Williamstown — five rooms above Mezze Bistro + Bar. The Williamstown alternative to the Williams Inn.
East Rock Inn in Great Barrington — 18-room boutique motel at the base of East Rock Mountain.
ButtonBall Inn in South Egremont — tucked into the historic village, cozy-but-curious.
Garden Gables Inn in Lenox — 18-room classic on five acres walking to Lenox Village.

The ownership question, broadly

Main Street Hospitality is not unusual. The Berkshires' consolidation pattern is replicated in the Hudson Valley (with Auberge, 1 Hotels, and others assembling properties), on Cape Cod (where Lark Hotels and Faraway/Salt Hotels have quietly built portfolios), in the Hamptons to a lesser extent, and in most mature Northeast travel regions.

The single-property owner-operator is becoming rarer. That's the main reason we hold the editorial line at ≤5 properties and highlight which operators fall where — not as a quality critique of the consolidators, but as a way to surface the operators who are still doing something structurally different.