THE BERKSHIRES, MA—"Would you like history with that?" might not be a farfetched question from the staff at many Berkshire County restaurants. Fine food prepared in legendary locations of scenic splendor has been a hallmark of the Berkshires for generations—and the tradition only grows.

One such venue is at the spectacular Wheatleigh Hotel in Lenox, next door to the Boston Symphony’s summer home, Tanglewood. A grand European palace based on a 16th century Florentine palazzo, Wheatleigh sits on a Berkshire knoll overlooking mountains surrounding a lake. This "summer cottage"—the ironic moniker of such Gilded Age mansions—was built in 1893 by Henry H. Cook, a New York City tycoon. A wedding present for his daughter, Georgie, who married a Spanish count, it was Cook’s reward to her for securing the family a title.

The prominent Boston architectural firm of Peabody and Stearns designed Wheatleigh. More than 150 artisans were brought from Italy to create intricate carvings, indoors and out. Landscape architect Frederick Law Olmsted, who designed New York’s Central Park, sculpted "Wheatleigh Park" from the surrounding property.

For many years, the estate was a working farm: the count and countess lived at their "cottage" only six weeks a year, holding grand summer parties. Wheatleigh is now a small elegantly appointed European-style hotel, offering a contemporary American interpretation of classic French cuisine. Visitors are transported to a yesteryear world of fine English wool carpeting, antique Waterford crystal chandeliers and hand-carved Chippendale chairs. Discreet, polished and professional service completes the effect.

Blantyre is likewise a turn of the century Lenox mansion offering sophisticated dining in a stunning formal setting. This Tudor-style mansion, built in 1902, replicates a grand Scottish Manor set amidst 100 acres of breathtaking Berkshire countryside. In the daytime, Blantyre is reminiscent of a private home, with fresh flowers on the center dining room table. In late afternoon, fine table linens, Gorham sterling silver, antique glassware and place settings appear, creating a world of serene European elegance. Blantyre complements its gourmet French cuisine with fine vintages from a wine cellar stocked with more than 600 selections.

Lenox’s Cranwell Resort, Spa & Golf Club features a magnificent brick Tudor mansion, on a hill commanding a 60-mile view. In the 1850s, the Reverend Henry Ward Beecher, brother of Uncle Tom’s Cabin author Harriet Beecher Stowe, built a farmhouse where Cranwell now stands. Rev. Beecher had presidential aspirations, which were scotched by his numerous romantic dalliances. In 1869, Gen. John F. Rathbone bought the property and moved Beecher’s farmhouse so his enormous new "cottage," Wyndhurst, would have a spectacular view. In 1896, John Sloane, co-owner of the famous furniture firm, W & J Sloane, purchased the property, tore down the original structures, and built the present Wyndhurst, which rivals the enormity and elegance of the first.

After turns as a hunt club and boy’s school (named for then-owner Edward Cranwell), Cranwell is today a premier four-season resort. Wyndhurst, an elegant formal dining room just off the Great Hall, offers magnificent expansive vistas and exquisite cuisine—hand-cut Black Angus, fresh seafood and pasta—and the experience of a luxurious bygone era.

Just south, in Stockbridge, is the Red Lion Inn, which traces its history to 1773. That year, Silas Pepoon established a small tavern as a coach stop on the dusty Albany to Boston road. After a succession of owners, Mr. and Mrs. Charles Plumb purchased the inn in 1862. Mrs. Plumb scouted area homes and farms for fine rare items; soon the inn was renowned for its colonial antiques. In 1896, the hotel was destroyed by fire, but Mrs. Plumb’s collection of colonial china, pictures, wearing apparel and furniture was saved.

Rebuilt at once, the inn reopened in May 1897. For more than 90 years, the inn remained with the Treadway family, descendants of the Plumbs. In 1968, Stockbridge residents Jack and Jane Fitzpatrick bought the property. Mrs. Fitzpatrick, rivaling Mrs. Plumb herself, has added hundreds of pieces to the Inn’s collection. The Red Lion is one of the few New England inns operating continuously since before 1800. Five presidents—Cleveland, McKinley, Theodore Roosevelt, Coolidge and Franklin Roosevelt—visited here, along with Nathaniel Hawthorne, Henry Wadsworth Longfellow, Thornton Wilder and more modern celebrities including John Wayne, Bob Dylan and James Taylor. In a setting imbued with history, visitors now enjoy Contemporary New England cuisine served in the Inn’s antique-filled dining room, tavern or courtyard.

Wheatleigh, Cranwell, Blantyre and the Red Lion Inn are but a handful of the establishments offering fine Berkshire dining in historic surroundings. Lenox’s Gateways Inn serves creative and contemporary American cuisine amid the incomparable elegance of the Harvey Proctor (of Proctor & Gamble) mansion. In nearby New Lebanon, NY, the Pillars Restaurant presents French and American cuisine in the former carriage house of the estate built by Abner Haight in 1834. The property’s history includes its notoriety as a Prohibition-era roadhouse and a 1930s gambling establishment.

The Morgan House in Lee, which now offers creative New England cuisine, was built in 1817 as a private home, and enlarged to become a stagecoach inn in 1855. Notable guests have included Grover Cleveland, Ulysses S. Grant and George Bernard Shaw. Rob Titus, the archaeologist who opened King Tut’s Tomb, held his annual Raccoon Hunting Banquets at the Morgan House. Further south, visitors can enjoy world class dining in a 1760 inn and former stagecoach relay at the Old Inn On The Green, New Marlborough. The inn features romantic candlelit dining rooms with fireplaces. The Egremont Inn, South Egremont, has served travelers for more than 200 years. It offers creative country cuisine.

At the Mill on the Floss, New Ashford, guests enjoy the elegant simplicity of French Country cuisine in the charm of an 18th century farmhouse with an open kitchen. Here, as at so many Berkshire restaurants, enjoy the ambiance of a distant, but not-to-be-forgotten, past.