About the Inn

The Inn has evolved from rooms to rent in a complex of adjoining buildings hosting a community of seasonal artists to what exists today: the one beautiful, historic building with its sweeping front porch and home to both unique timeshare and condominium units year round.

Summery Exterior at Hillcrest Inn Resort

The History of the Inn

In the book Wish You Were Here – An Album of Messages and Memories From Old Ogunquit published in 2022, co-author Kenney Bassett captures this history of the Hillcrest Inn, citing its deep roots in the arts community of Ogunquit.

Front Porch in Summer
Dusk Exterior at Hillcrest Inn Resort


Established in 1911, the Hillcrest Inn opened for business in 1913, operating as a summer hotel with 50 rooms. In the early years, it served as a boarding house for summer art students in part because of its proximity to the cove. The builder, Henry Wallace Weare (1868-1937), was recognized by Harrie B. Coe in 1928’s Maine Biographies as having “been most successful in his hotel venture.”  Coe also noted that he was “…prominent among public-spirited men of Ogunquit, who also operates extensively in the real estate market.”

Antique Postcard of Hillcrest Inn
View from Front Porch in the 1920's


By the late 1920’s the Hillcrest Inn could accommodate 100 guests. By this time, especially in nearby Perkins Cove, Ogunquit had become a thriving art colony where “the pursuit of art was a form of leisure”.


After Henry W. Weare’s death, his son, George Dunlap Weare (1896-1991) took over the Hillcrest Inn with his wife, Helen (Shum) Weare (1899-1977). This same year was when the new Ogunquit Playhouse first opened its doors.


By 1952 the Hillcrest Inn could accommodate up to 85 guests. The earlier wraparound porch at the far-right corner had been enclosed to make a new reading room. The dining room served three meals a day, and freshly prepared roasts of beef and turkey were on the menu every evening.


George and Helen Weare sold the Inn along with several smaller adjoining parcels to artist J. Phillip “Phil” Richards (1906-1991) and his wife Hilda Harries Richards (1906-1975). Phil was a fine arts professor at Wilkes College in Wilkes-Barre, PA and nationally recognized with awards from the American Watercolor Society. During his ownership of the Hillcrest Inn, he hosted summer art workshops. Phil and Hilda went on to run the Hillcrest Inn until 1975.

1984 – Present

Leonard “Skip” Clark purchased the Hillcrest Inn and adjoining buildings in 1984, converting them to condominium and apartment units. In 2010 the Hillcrest Inn became an independent association, separate from any adjoining buildings.

For more history on the Hillcrest Inn Resort and the surrounding area also visit the Historical Society of Wells And Ogunquit, and the Ogunquit Heritage Museum.

View from Parking Lot in the 1950's
Postcard from the 1950's
Postcard from the early 1910's
From a postcard dated August 15, 1915

Hillcrest Inn
Ogunquit, Me.

Dear Emily,
My seven delightful weeks at Ogunquit are nearing their close. I leave Monday on the 9AM train for Solon Me. to connect with the 8:00 Boston Express due in Portland 11AM will have three quarters of an hour wait there. If you are not engaged from 10:15 to 11, should love to have a little visit with you in the Portland Station.

Your kind invitation to visit you is much appreciated I assure you, but my time to the various relatives is so limited that I feel I must hurry or lest I mortally offend—Hoping that all is well with you and that we may meet Monday.”

E. Coolidge


Hillcrest Inn Resort is a beautiful, historic building with a sweeping front porch and all the charm of the past blended with today’s amenities. Home to a year-round unique association of 18 condominium units, varying options exist to stay or own in this Maine coastal community.  

No smoking and no pets are allowed anywhere on the property, for the comfort of our owners and guests.

Hillcrest Inn Resort is affiliated with the RCI vacation exchange network.


512 Shore Road
Ogunquit, Maine 03907