The Raymond Hotel located in South Pasadena was the first major resort hotel of the San Gabriel Valley which, for the most part, served as a winter residence for wealthy easterners. It was built by Mr. Walter Raymond of Raymond & Whitcomb Travel Agency of Boston, Mass. The hotel was built atop Bacon Hill which lies between Pasadena and South Pasadena and was renamed Raymond Hill with the opening of the hotel in 1886. The original hotel, a grand and unequivocal Victorian edifice was burned to the ground in 1895. A second building, of a later and more fireproof style, was erected in 1901 and equally replaced the older in grandeur. The hotel was foreclosed following the Great Depression and was razed for commercial development.
In 1883 Walter Raymond had ventured west the young community of Pasadena, California, described as a sleepy village of 1,500 people. Seeking to excite business in the transcontinental tour market, he noticed that the yet unincorporated town had no hotels for visitors. This piqued his interest in establishing one, thereby purchasing a hard granite hilltop called Bacon Hill as the site for his new Raymond Hotel. The dynamiting and grading off of 35 feet (11 m) of the hilltop came to more than the twice Raymond’s estimates, and he turned to his father Emmons Raymond for assistance. The older Raymond was president of the Boston & Passumsic Railroad and one of the 40 original stockholders of the Santa Fe Railroad.
Interested in at least surveying the site of the hotel, Emmons arrived in Pasadena during a downpour and sat under an oak tree listening to his son expound over the beauty of the Southern California area. But the rain poured down leaving Walter hopeless in convincing Emmons. When the sun finally did break through the clouded sky it was a sight the old man had never experienced in his life and he agreed to finance the rest of Walter’s construction.
The new Raymond Hotel opened with a gala ball on November 17, 1886, and enjoyed nine successful seasons (winters). However, the original structure was a wood framed Victorian with a shingled roof boasting some 200 rooms — and 80 chimneys.
On Easter Sunday 1895, a spark from a chimney set the roof on fire and the hotel and all its contents burned to the ground in 40 minutes. At the time there were 165 guests staying at the hotel, but most were at church, and as fortune would have it, no one was hurt though all their possessions were lost.
Walter Raymond was not to be disheartened by this loss since he had caught the Southern California fever. He immediately began promoting the area through publications and authors of publications who could attest to the virtues of the area. He attempted to augment the insurance money through a $250,000 bond issue, but there were too few people in the area with enough money to support it. Finally, a good friend and seasonal resident of the hotel, Mr. Richard T. Crane of Crane Plumbing, Chicago, agreed to a $300,000 mortgage which was applied to the building of a second hotel.