The town of Jackson became a significant summer resort later that North Conway, Intervale or other White Mountain communities. Artists including Boardman, Geary, Clark, Hoit and Brackett were among the first visitors to discover Jackson; the earliest came as early as 1847. But it was not until the summer of 1858 that Joshua B. Trickey opened a lodging establishment, the Jackson Falls House, in Jackson. This was followed by the opening of the Iron Mountain House in 1861 (it burnt in 1877). The Thorn Mountain House was built and opened to the public in 1869, followed by the Glen-Ellis in 1876 and the first Eagle Mountain House in 1879. The opening of the Portland and Ogdensburg Railroad in the early 1870s gave a tremendous push to the popularity of the area as a tourist destination. Many of Jackson’s visitors were transported from the Glen train station in nearby Bartlett which was on the Portland & Ogdensburg line.
In 1876, the covered bridge which spans the Ellis River was built by Charles Austin Broughton and his son Frank. At that time it was named the "Honeymoon Bridge". Local custom has carried on a romantic tradition with many newly married couples having their photograph taken there, thus adding another memory to their special day. Jackson's Covered Bridge (No. 51), a Paddleford truss construction, is one of 55 remaining in the State of New Hampshire today. The bridge is owned and maintained by the State of New Hampshire and is protected by a fire protection system to alert the local fire station.
In 1860 Jackson village included approximately fifteen buildings on both sides of the Wildcat River. On the west side of the Wildcat River there was a clothespin factory and saw mill, a post office, a church, a school, a blacksmith shop, two stores, and grist mill. Today, only the church remains. Other buildings located on the east side of the river were a store, a school, several houses and the Jackson Falls House. In 1879 George Pinkham deeded a parcel of land to the Town of Jackson. The land, located below a bowling alley, formerly housed a shop. The town hall was later built on the site.
By the late 19th century Jackson had developed into one of the region’s most active and successful tourist centers. In 1885 the Jackson Falls House was raised and an additional story was inserted underneath the original building. The second Iron Mountain House and the first Gray’s Inn were also constructed in 1885. The most significant local development in the category of tourism however, undoubtedly was the redevelopment of what had been known as Thorn Mountain House into Wentworth Hall in the 1880s under the watchful eye of General Marshall C. Wentworth and his wife Georgia. The Wentworth's based their plan for the property on the “cottage system” hotel management then popular in Great Britain. A complex of a group of buildings was designed, providing most of the lodging in separate cottages grouped around a main service building. In 1886 the Casino was erected and attached to the south side of Thorn Mountain House and a large stable was built, able to accommodate 30 to 60 horses. A hydroelectric plant was constructed in 1894 and by the end of the century, the complex consisted of over twenty buildings. In the 1890s General Wentworth built a water-powered generator on the Wildcat River which totally electrified the hotel and remained in working condition until 1975.
Supplementing the accommodations available at Jackson’s larger hotels, the village also saw the construction of other seasonal residences including smaller cottages and converted farmhouses, situated on the surrounding hillsides, in close proximity to the village center. The summer residents, mostly from Boston but also from New York, Philadelphia and other eastern locations, left their imprint on the larger village as well. The Jackson Free Public Library was constructed in 1901 with Frank Shapleigh securing plans for the building from architect William Ralph Emerson. The town hall was built in 1896 and an addition was made about 1910. The village school, originally constructed in about 1860, was also added onto at about the same time.
By the 1920s, up to forty trains per day were delivering travelers to Jackson. In the early 20th century the capacity of Wentworth Hall and Cottages peaked at 350. General Wentworth died in 1915, and Mrs. Wentworth sold the hotel complex to Nathan and Estelle Amster, a wealthy Jewish couple from New York. Nathan Amster had made his fortune in mining, railroads and as a founder of New York’s Third Avenue El. Under their ownership, the Wentworth became the exclusive domain of wealthy Jews from the northeast, and anyone wishing to stay would have to be recommended by other patrons. In 1916 the new owners acquired the Glen Ellis House, a mansard-roofed hotel originally constructed in 1875-6 and utilized it as a 100-guest annex, bringing the total capacity of Wentworth Hall to 350. The building was demolished in 1982.
A fire destroyed most of the businesses in the village in 1924. In 1931 the bridge which crossed the Wildcat River near the Town Hall was replaced by a new stone bridge located downstream, and the Jackson Public Library was moved a short distance to a new location to make way for the new bridge.
Estelle Amster continued to own the Wentworth Hall hotel complex as well as Wentworth Castle until 1946. The Wentworth Hall property was bought by Harry Schiener and E.M. Loew, the movie theater magnate, in 1950. Two orchestras played in the casino which could seat 400 people. Among the entertainers who brought their acts here were Alan King, Harry Belafonte, Zero Mostel and Jackie Mason. However, the days of summer vacationing at grand hotels were quickly becoming a thing of the past. In the years following World War II, escalating costs and changing vacation patterns made large hotels increasingly unprofitable to operate. The decline of Wentworth Hall and most of New England’s resort hotels began in the early 1960s.