The History of Simmons' Way Village Inn & Restaurant Simmons' Way was named in honor of E. W. Simmons, a prominent educator, statesman and lawyer who built the original manse in 1854. Born of Dutch heritage in Dutchess County, he became the first merchant in the village when he built the general store next to the railway station in 1851. His modest home was transformed into an elegant Victorian residence in 1892 by E.H. Thompson, then president of Millerton National Bank.

Since 1903 the house has served as doctors' residences until, inevitably, it evolved into its present role as a grand country inn. The purchase of the property by innkeepers Richard and Nancy Carter in 1987 is a culmination of a renovation process begun in 1983. So admired is Simmons' Way that it's photo was featured on the cover and in the lead article of New Yorker Magazine, featuring the elegant country inns of the North East.

Simmons' Way has been featured in the leading inn directories including Country Inns and Backroads, AAA, Mobile Travel Guide and the Star Service Guide. The inn was elected a Great Inn of America in 1988. American Express selected Simmons' Way Village Inn as the quintessential Country Inn (1991) for a weekend getaway national advertising campaign. More recently, the inn and the restaurant were awarded the coveted four star rating by the Gannett papers.