Skip to content

Welcome to Cape Cod

Chequesset Inn: Wellfleet

Chequesset Inn post card.
Photo courtesy of the Wellfleet Historical Society.

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. 

Walking the boardwalk, Chequesset Inn.
Photo courtesy of the Wellfleet Historical

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

The Pines.
Photo courtesy of the Historical Society of Santuit and 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. 

Ellen Jane McKean, daughter of Mr. and Mrs. Kirk O’Ferrall, Dean of the Cathedral of Detroit, photographed bathing at the Pines, Cotuit, Cape Cod, where they are spending their vacations. Cape Cod Chamber of Commerce Collection, The William Brewster Nickerson Cape Cod History Archives.

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.

You might also like:

Latest Editions

  • Stay Connected

    Sign up for our newsletter
  • This field is for validation purposes and should be left unchanged.