Woodstock’s origins began in the waning days of British America, when the colonial Governor of New Hampshire, Benning Wentworth, first allowed British colonists to settle the land in 1761. At the time, the Province of New Hampshire claimed suzerainty over the area that now constitutes Vermont, often quarreling with New York to administer the territory. Governor Wentworth specifically allowed David Page and several dozen other families to settle the region by means of a royal land grant. Over time, more colonists from other the other New England colonies started to establish homesteads upon ground the original settlers had yet to occupy. They christened their new community after the town of Woodstock in Oxfordshire, England. On the outskirts of that Woodstock resided the regal estate of Blenheim Palace and its owner, George Spencer, the 4th Duke of Marlborough. As such, the residents of the new Woodstock felt bound to carry the memory of the lord over to the “New World.” While those families raised farms throughout the surrounding countryside, an actual village square did not emerge until James Sanderson and his family arrived around six years later. Then, in 1776, Major Joab Hoisington provided a much-needed source of income for the nascent town, constructing a gristmill and sawmill along the Qttauquechee River.

When the American Revolutionary War erupted in the mid-1770s, settlement to Woodstock slowed considerably. Yet, it picked up again once the conflict ended in 1783. The town itself soon became one of the many communities that was governed by the separate Vermont Republic, which first emerged during the Revolution. It eventually joined the United States, with the rest of the Vermont in 1791. Woodstock received a wonderful honor nearly two decades later, when the Vermont General Assembly decided to meet in the town before permanently relocating to Montpelier the following year. Factories soon began to emerge throughout Woodstock due to the strong currents of the Qttauquechee River, giving the locals a source of employment. The businesses originally produced products made of wood, such as scythes, axes, and carding machines. But as the manufacturing processes became more intricate, the plants created everything from carriages to luggage trunks. Its economic vibrancy had become so great that some 3,000 people lived in the town on the eve of the American Civil War.

Toward the end of the 19th century, the town experienced several new economic booms. One of the first began with the arrival of the Woodstock Railroad network in neighboring White River Junction in 1875. Not only did more people start to travel to Woodstock, but local merchants and industrialists started to move more goods to other markets across the nation. But as those passengers began to explore the surrounding countryside, they decided to vacation for long periods of time. Many were soon attracted to the sloping geography near Woodstock, making the town an exclusive destination for outdoor enthusiasts. Seasonal guest homes soon dotted the landscape, as well as a few hotels and inns. The greatest of those locations was the Woodstock Inn, which aspiring hoteliers developed from the Eagle Hotel in 1892. The hills and mountains near Woodstock also emerged at the sight of popular ski trails, the most notable of which was Suicide Hill. As the 20th century dawned, the town had firmly established itself as one of New England’s most luxurious holiday destination. Woodstock has maintained that identity ever since, with the great Woodstock Inn & Resort playing a central role in maintaining that status.

Throughout its history (and various iterations) the Woodstock Inn & Resort has displayed one prominent architectural style: Federal. Federal architecture dominated American cities and towns during the nation’s formative years, which historians now best identity as lasting from 1780 to 1840. The name itself is a tribute to that period, in which America’s first political leaders sought to establish the foundations of the current federal government. Fundamentally, the architectural form had evolved from the earlier Georgian design principles that had greatly influenced both British and American culture throughout most of the 18th century. The similarities between the two art forms have even inspired some scholars to refer to Federalist architecture as a mere refinement of the earlier Georgian aesthetic. Oddly enough, though, the architect deemed responsible for popularizing Federal style in the United States, was in fact, not an American. Robert Adams was the United Kingdom’s most popular architect at the time, with his work largely involved providing his own spin on the infusion of neoclassical design principles with Georgian architecture. (This is also the reason why some refer to Federal architecture as “Adam-style architecture.”) As such, his new variation spread quickly across England, defining its civic landscape for much of the Napoleonic Era. Despite the bitter resentments that most Americans harbored toward Great Britain at the time, their cultural perceptions of the world were still largely influenced by the old mother country. Thus, Adams’ new take on Georgian architecture rapidly spread throughout the United States as it had previously across the Atlantic.

Unlike many other popular American architectural forms, Federal style is easily recognizable due to its unique symmetrical and geometric design elements. Most structures created with Federal architecture typically stand two to three stories in height and are rectangular (sometimes square) in their overall shape. While the buildings normally extended two rooms in width, larger structures would usually contain several more. In some cases, circular or oval-shaped rooms functioned as the center living space. The outside façade of a Federal-style building was simplistic in their appearance, although some detailed brass and iron decorations made their appearance, too. Perhaps the most common form that the ornamentations assumed were elliptical figures, as well as circular and fan-shaped motifs. Architects concentrated those features around the front entrance, where cornices, iron molding, and a beautifully sculpted fanlight resided. (Fanlights are a regular design element for Federalist buildings, appearing in other locations throughout the top of the structure, as well). The exterior walls themselves were primarily composed of clapboard out in the country but consisted of brick in urban areas. Palladian-themed windows also proliferated throughout the façade, installed in a way that conveyed a deep sense of balance. Roofing was also hipped and contained simple gables and dormers that allowed for natural light to more easily infiltrate the upper echelons of the structure.