Historic Dining

America is a young country, its oldest buildings dating back only a few hundred years. The oldest of those buildings tend to cluster along the eastern seaboard, with Massachusetts and Connecticut being especially rich in architectural legacies. Many of these ancient structures have found new life as restaurants and inns, allowing visitors to savor the aura of the past while enjoying modern cuisines.

Here is just a sampling of regional hostelries redolent of the nation’s past.

Those with a yen for history will want to seek out the New Boston Inn at the junction of routes 57 and 8 in Sandisfield MA, put on the National Register of Historic Places in 1988 and claiming the title of the oldest inn in Berkshire County. As with many structures that originated in the Bay State’s western migration, the building has been expanded and improved over the centuries, but its 1737 Tavern offers a rare glimpse of the actual dimensions of the earliest buildings.

To prove their deeds, 18th-century settlers had to build homes at least 18 feet square and the tiny tavern room, the oldest part of the inn, reflects that requirement. By 1760, however, a handsome addition had been added to the front to welcome stagecoach travelers, a tradition that continues today—although today’s sojourners travel by car rather than bone-shaking coaches.

Over the centuries, there have been notable visitors, such as Revolutionary War hero Henry Knox who passed through on his forced-march expedition to bring cannons to Boston for the battle of Bunker Hill and in 1838 General Winfield Scott, hero of the War of 1812 and the Mexican War. In the 20th century, film stars Elizabeth Taylor and Richard Burton, visited the tavern.

The inn serves both pub food and dinners and has seven rooms for overnight guests. A ballroom with vaulted ceilings is available for special events. It even has a resident ghost.

Sandisfield and New Marlborough are remote communities today but in the 18th and 19th centuries they were on stage routes carrying travelers from larger American cities to growing communities such as Albany. Blissfully bucolic New Marlborough has another relic of early America in its Old Inn on the Green, an upscale, elegant restaurant and inn. Here the owners have carefully preserved the past, serving dinner by candlelight and, in colder weather, lighting the fireplace in the dining room. Stenciling on the walls mirrors the décor employed in the 18th and 19th centuries, all an evocative backdrop for the exquisite cuisine served by chef Peter Platt.

Like the New Boston Inn, the Old Inn on the Green, 134 Hartsville-New Marlboro Road, began life as a stagecoach stop in Early America. The building is said to date from 1760 and it became a bustling stop on the Red Bird Stagecoach Line in 1834. Today it is a reminder of this colorful era and offers authentically restored guest rooms and intimate dining experiences. During warmer weather, al fresco dining is available on the canopied garden terrace off the taproom. The beautiful inn was named the top historic inn in New England by Yankee magazine in 2011.

The Red Lion Inn is more visible to visitors to the Berkshires, occupying the corner where routes 7 and 102 intersect on Stockbridge’s busy Main Street. According to oral tradition, the inn dates to the early 1700s. In 1773, Silas Pepoon specifically constructed the building as a tavern, christening his business the Red Lion Inn. It too has played its role in American history, serving as a gathering place for angry citizens when they assembled to pass resolutions protesting the British Parliament’s Intolerable Acts.

The inn has grown and evolved over the years and today recalls the elegance of the Gilded Age when visitors flocked to Stockbridge to enjoy the region’s cultural delights. By the height of the Gilded Age, the size of The Red Lion Inn had grown to accommodate around 100 guests. Some of America’s most prominent individuals visited over the following decades including contemporary cultural icons such as Nathaniel Hawthorne, William Cullen Bryant, Thornton Wilder, and Henry Wadsworth Longfellow. The inn even hosted several U.S. Presidents, including Grover Cleveland, William McKinley, Theodore Roosevelt, Calvin Coolidge and Franklin Delano Roosevelt.

In 1968 Jack and Jane Fitzpatrick purchased the inn and continued to upgrade it, outfitting its interiors with even more colonial décor. The Fitzpatrick family remains the steward of this historic inn which now offers contemporary regional cuisine in its elegant main dining room, a cozy Colonial eatery known as Widow Bingham’s Tavern, the Lion’s Den Pub and a flower-filled courtyard dining experience in warm weather.

Farther south in Sheffield history lives on at the The Stagecoach Tavern. The location has the earliest origin of any of the historic inns, having become the property of Johan Reyes (Race), who escaped the feudal constraints of the Dutch great manors in New York State to make his home there in the late 1600s. In the 1750s Colonel Frederic Andrews and Reyes’ descendant James Race built a farmhouse that is now the tavern’s dining area. In 1829, when the burgeoning stagecoach business sought places for travelers to stop and teams of horses to be changed, the Giles Andrews Tavern was born.

The inn has known a series of owners since. For the past 21 years, it has been operated by the Rothstein family who have maintained the cozy feel of fireplaces, heavy wooden beams and comfort foods crafted from produce from local farms. Try the braised beef for a hearty, traditional New England meal.

Some venues did not start out as eateries. Old Mill at 53 Main Street in South Egremont is one of these. Its original function was food oriented however, serving as a grist mill where local farms could convert their oats, rye and wheat to flour to feed their families. Today, the 1797 mill—whose millstones and original waterwheel are now incorporated in the grist mill at Sturbridge Village—is a perennial favorite for dining among locals and visitors to the region.

It was converted to a restaurant in 1978 by Terry Moore who retained its rich woodwork, exposed beams and aged floors but imbued it with a sharp, contemporary feel that is echoed in his “seasonal contemporary New England cuisine and traditional favorites.” A wood-burning forge creates a cozy atmosphere, perfect for a special occasion or dinner with friends.

Across the Connecticut state line, we come to another long-time favorite The White Hart. Like many of the early inns, the White Hart started in 1806 as a personal dwelling that took in travelers. By 1867 Salisbury was a busy town, filled with visitors, and a large addition was constructed. Over the centuries the business has had a long series of owners, including Edsel Ford, son of Henry Ford, who was said to have bought it because he wanted a place to stay while his son attended nearby Hotchkiss School.

The inn was the birthplace of the renowned Harney Teas, now an international favorite (it is even served in Buckingham Palace). The company’s storied history began when tea master Stanley Mason demanded to know why innkeeper John Harney was serving insipid teas made from tea bags. Intrigued, Harney plumbed Mason’s long experience and began mixing teas in the inn’s basement.

The White Hart underwent a large-scale renovation in 2010 and was reimagined and reopened in 2014. The property features 16 guest rooms, three dining rooms, a taproom with a full-service bar, two outdoor dining patios, a large porch with drink service, a ballroom and café.

Skipping down Route 7 to Kent, we encounter another vintage building transformed for modern usage. The Swift-Bull House bears the name of two families who owned it for 177 years before it became a prime business location in downtown Kent. It was built about 1781 by Asaph Swift. Originally a one-story home of about 1,000 square feet, it was enlarged over the years to accommodate growing families. It was sold in 1918 to carpenter and clockmaker Eugene Bull.

The building has known other uses as well, serving as a place of worship for Episcopalians before St. Andrew’s Church was built in 1826 and later as a “lubritorium,” servicing early automobiles.

On the basis of extensive research, a restoration was undertaken in 2016, preserving the post-and-beam frame, matching original materials and respecting historic methods of construction. Today the structure is home to two restaurants, Swyft (spelling of the name varied over the generations) and Orehill, Orehill and Swyft.

The lively Swyft Tavern serves wood-fired pizzas, small plates and seasonal entrees. Craft beers, cocktails and wine lists offer familiar favorites and new discoveries. Ore Hill, on the other hand, offers an intimate tasting menu and evokes a quiet oasis.