Today life is all about speed and instant gratification. Innovations like smartphones, GPS, high-speed internet, streaming music and movies, have taken a lot of the work out of what were time consuming tasks.

The invention of the freeway in the 20th century made getting from Point A to Point B a breeze no matter the distance. Not very long ago, innovations like these were mostly science fiction. In the early 20th century life was slower. The new technology consisted of radio, vinyl records, motion picture theaters, and microwave ovens.

Weeks long ambles were the norm, giving time to soak in every blade of grass and grain of sand that existed. In the days before the Mid-Cape Highway connected the entirety of Cape Cod, vacations here were often spent in one location. The precursors to the modern hotel chains worked hard to make their property all-inclusive and unique, giving visitors their money’s worth even if they only saw a little of the Cape.

These are a few of those iconic Olde Cape Cod lodging choices that stood out from the rest for those looking for their own slice of paradise on the Cape.

Highland House: Truro

One of the originals of Cape Cod hospitality, the Highland House, began as a simple farmhouse in the shadow of Highland Lighthouse. Land originally owned by Isaac Small was passed down to his sons Joshua and James upon his death in 1816. It was James who built the farmhouse in 1835. 

Author Henry David Thoreau paid four visits to Cape Cod between 1849 – 1857. Thoreau would spend the night at the lighthouse keeper’s house with James Small and his family. During one stay, James remarked to Thoreau that his farmhouse had room for several boarders. Thoreau thought this a wonderful idea. Though not specifically advertising rooms for rent at the time, Highland House rather quietly opened in 1861.

Business saw tremendous growth though with the release of Thoreau’s “Cape Cod” along with the extension of the railroad line into Provincetown in 1873. Highland House was routinely filled throughout the summer season. Morton Small took over the property upon his father’s death in 1874. In 1876, a two-story wing was built on the farmhouse, doubling its size to take advantage of the increasing tourism.

With Highland House at only forty rooms, Morton Small decided in 1906 to have a new hotel, the Highland House Annex, constructed in time for the 1907 season. The original hotel was eventually moved to Old County Road in South Truro. The new Highland House had a large piazza where the dinner bell was tolled. Beach access became easier thanks to a staircase leading down the cliffs. The property even had a bowling alley.

Between 1898-1928 several cottages were built on the Small property with names including: Millstone, Rock, Beacon, Ship, Margaret Adams, Mayflower, and Pilgrim. With the increasing popularity of automobiles, stays at the hotel began to slow in the early first half of the 20th century. It remained in the Small family until 1947 when it was purchased by Eddie Mayo, Second Baseman of the Detroit Tigers and former Minor League baseball player Hal Conklin. The creation of the Cape Cod National Seashore in 1961 complicated the status of the Highland House. It remained a hotel and restaurant through the 1960’s. The building was saved from demolition when it was repurposed as the Truro Historical Society.

Aberdeen Hall: West Yarmouth

In the late 19th and early 20th centuries the community of Great Island in West Yarmouth was open to the public. The centerpiece of the Great Island vacation experience was a high-class country club named Aberdeen Hall. Built by ornithologist Charles Cory using his inherited family fortune in 1902 the forty-five room property was frequented by fellow social elites by invite only. However, in 1905 Cory leased his country club to E.M. Guild for use as a first-class hotel. It was an immediate success.

In January 1909 Cory sold the entirety of Great Island including Aberdeen Hall to New York steel magnate Henry Phipps. Phipps immediately got to work improving Aberdeen Hall and heavily promoting it as the “only 1st class hotel on Cape.” Phipps had a large addition built in May 1909.

Offering private baths, fine dining, fishing, walks in the pine and oak tree groves, as well as rounds on the golf links, it was no wonder Aberdeen Hall was the place to be. For those not able to make it to the hotel via automobile or on foot a ferry service was put into place shuttling people over from the Ocean Street docks in Hyannis. 

Even after Rhode Island banker Malcolm Chace purchased Great Island in 1914, he kept Aberdeen Hall running smoothly. In fact, the hotel saw its greatest heights in terms of occupancy, including its most successful season of 1919 after Chace’s purchase. Sadly, a fire on August 3, 1924 put an end to the resort hotel and by extension ended Great Island’s public access. Nearly a century later, the vast majority of the property is owned by the Chace family and is one of the most restricted locations on all of Cape Cod.

Chequesset Inn: Wellfleet

The “Grand Hotel of the Outer Cape,” the “Hotel Over the Sea,” whatever its nickname the Chequesset Inn truly was a one-of-a-kind Cape Cod luxury resort. Wellfleet was predominantly known as a fishing village in the latter part of the 19th century. As the fishing industry wound down Captain Lorenzo Dow Baker wanted to increase the town’s appeal. He achieved this with the construction of the Chequesset Inn in 1886. The sixty-two room, four-story resort was built on the 400-foot long Mercantile Wharf near Mayo Beach. It quickly turned Wellfleet into a summer resort town.

The guests at the Chequesset Inn were treated to high end luxury in more than one area. Amenities there included both sea and freshwater fishing, boating, tennis, billiards, and bowling. The meals included music played by a live orchestra and vegetables grown from the inn’s own gardens. Guests could be taken to nearby ponds, or walk down Kendrick Avenue to soak up the sun at Mayo Beach. 

Chequesset Inn changed and evolved with the invention of electric power and then the development of the automobile. This helped it remain a huge success for more than four decades. However, harsh New England winters, which could create vicious icebergs, wreaked havoc on the wharf. After years of peril the sea claimed the Chequesset Inn. 

In early 1934, after a particularly frigid winter, Wellfleet Harbor was packed with ice. During a strong winter, storm chunks of ice became free and destroyed parts of the wharf, causing the partial collapse of the inn. Luckily, being a summer resort, nobody was hurt in the collapse. The Chequesset Inn never reopened and was dismantled in September 1934 bringing the era of Wellfeet’s “grand hotel” to an end.

The Pines: Cotuit

A village of Barnstable, Cotuit was home to an icon of Cape Cod hospitality: The Pines. It overlooked Cotuit Bay and lasted for six decades around the turn of the 20th century.

The story of The Pines began in 1808 with a homestead built in Brewster by carpenter Samuel Dottridge. When the family moved from Brewster to Cotuit the home was pulled by oxen to Ocean View Avenue. By 1848 the Dottridge property included a five-room home on forty-five acres of land and was passed down in the family. 

In 1891 Elizabeth Morse, Samuel’s granddaughter, opened a boarding house in the homestead. The following year Elizabeth and husband John built a three-story building with thirty-three rooms on the property. On June 17, 1893 The Pines hotel had its grand opening. 

Being family-friendly there was no alcohol or gambling. However, there was a private beach on Cotuit Bay, high quality food, an ice cream parlor, sailboats for rent, and even rides to nearby ponds. The Pines was an immediate hit allowing Elizabeth and John to enlarge the hotel itself at the turn of the 20th century. It continued with the purchasing of retired sea captains’ cottages which surrounded The Pines, adding rooms to the hotel without building an addition. 

The Pines was inherited by Elizabeth and John’s daughter Nita Crawford and her husband Calvin in 1910. In 1920 they purchased a neighboring home, renovating it into the Pine Tree Tea Room. This became another family attraction serving ice cream and sodas. 

Shortly after World War II a twenty-four room mansion known as Evergreen located near the resort was purchased and added to The Pines. The 1950’s brought the Mid-Cape Highway and marked changes for many hotels of the time. The Pines survived on its legacy until after sixty-five years the Crawfords brought the curtain down on The Pines in 1958. 

In an interesting full-circle story the cottages and the hotel itself were sold or dismantled after The Pines closed. The only remnant left standing for the public to visit is ironically the spot that started it all: The Samuel Dottridge homestead. Today it houses the Historical Society of Santuit and Cotuit. 

Cape Cod in the 21st Century is still home to many unique, iconic, and beloved resorts and hotels. These establishments of yesterday helped pave the way for them. They are a part of the history of Olde Cape Cod, the way things used to be in simpler times. Those days when hand-cranked automobiles, phonographs, and televisions were new and exciting are long gone but never forgotten.

Christopher Setterlund is the author of Iconic Hotels and Motels of Cape Cod and contributing writer for Cape Cod Life Publications.