Explore one of Palm Springs’ distinctive residential neighborhoods on this self-guided bike tour through Deepwell Ranch Estates. The route combines Hollywood history, quiet residential streets, and architectural styles that reflect the city’s evolution from a desert retreat into a celebrated destination.
Along the way, you’ll pass homes associated with entertainers and notable figures, including Ginny Simms, Loretta Young, Carmen Miranda, Marjorie Main, Robert Livingston, Oscar Mayer, Jerry Lewis, and William Holden. The homes are privately owned, so enjoy the architecture and history from the public street.
The History of Deepwell Ranch Estates
Deepwell’s story began long before its celebrity residents arrived.
In 1895, George Fitch, an editor of the San Francisco Chronicle, purchased the land and planted an apricot orchard. Following a decade of drought, Oliver McKinney and his wife, Rose, arrived in Palm Springs in 1911 and leased the Fitch property. They planted castor bean trees to supply castor oil to the U.S. armed forces, but their plans faltered when the water supply was shut off.
In 1926, scientist and writer Henry Parsons took over the property. He drilled for water and eventually reached a depth of 613 feet. Parsons named the property Deep Well, and the name endured.
Parsons sold the property to Charles Doyle in 1928. Doyle turned it into Deep Well Guest Ranch, and it remained a ranch through several ownership changes. In 1951, developer William Grant purchased the land and subdivided it into a custom-home neighborhood.
Today, Deepwell Ranch Estates features a mix of Spanish Colonial Revival, Ranch, and midcentury modern architecture. Its residential streets offer a glimpse of the varied architectural styles that define Palm Springs.
Getting a Bike for Your Deepwell Tour
You don’t need to bring a bicycle to explore Deepwell Ranch Estates. Some Palm Springs hotels and resorts offer complimentary bicycles, while others can recommend nearby rental options. Check with your hotel before you visit to see whether bikes are available, whether reservations are required, and whether there are any rental fees.
Need a bike? Bike Palm Springs Rentals & Tours offers bicycle rentals at 194 S. Indian Canyon Drive in downtown Palm Springs. The shop is a potential starting point for visitors who need a bike before heading to Deepwell Ranch Estates. Check current hours and reserve your bike in advance, especially during the busy season. It's about a 10-minute bike ride from Bike Palm Springs to the tour start in Deepwell.
Start Your Deepwell Bike Tour
Starting point: The corner of Indian Trail and East Palm Canyon Drive.
From the intersection, follow Indian Trail as it angles right onto Camino Real. At the split, you’ll see Villa Royale, a Spanish-style boutique hotel that appeared in Mad Men's second season.
Continue along Camino Real to Calle Palo Fierro, turning right. Follow the road to Mesquite Avenue, then turn right to explore the neighborhood’s historic homes.
Ginny Simms – 1139 Mesquite Ave.
Ginny Simms (1909 - 1994) was a popular singer and actress whose warm voice made her a radio favorite. She rose to prominence as the featured vocalist with Kay Kyser’s Orchestra during the 1930s and 1940s before pursuing a successful solo career.
Simms also appeared in Hollywood films, including That’s Right—You’re Wrong and You’ll Find Out, and hosted her own radio program. Later in life, she devoted considerable attention to charitable work, particularly causes supporting veterans and hospitals.
A longtime Palm Springs resident, Simms was part of the entertainment community that helped shape the city’s reputation as a retreat for Hollywood figures. She is seen here at the 1957 Palm Springs Police Show.
Credit: Palm Springs Historical Society
Loretta Young – 1075 S Manzanita Avenue, at Mesquite.
Academy Award-winning actress Loretta Young (1913–2000) was among the major Hollywood personalities who spent time in the Palm Springs area during the studio era.
Young won an Oscar for The Farmer’s Daughter and later starred in The Loretta Young Show, earning an Emmy for her television work. During the 1930s and 1940s, Palm Springs offered actors a convenient desert escape while keeping them within the distance limits imposed by Hollywood studios.
Known for her elegant screen presence and personal style, Young moved in the same social circles as fellow stars such as Clark Gable, Cary Grant, and Bob Hope.
Studio Image, 1943
Continue along Mesquite and turn right on Calle Rolph.
Carmen Maranda – 1044 Calle Rolph
Carmen Miranda (1909–1955), famously known as the “Brazilian Bombshell,” was a singer, dancer, and actress whose colorful costumes and fruit-adorned hats became her trademark.
Born in Portugal and raised in Brazil, Miranda first became a major entertainment star in Brazil before arriving in the United States in 1939. She later appeared in Hollywood musicals, including Down Argentine Way (1940) and The Gang’s All Here (1943).
During World War II, Miranda became one of the most recognizable entertainers in the United States and an internationally known symbol of Latin American popular culture. She called her Palm Springs residence home during her career.
Marjorie Main – 1280 Calle Rolph
Marjorie Main (1890–1975) was a character actress known for her distinctive voice, direct manner, and memorable portrayals of practical, no-nonsense women.
Born Mary Tomlinson, she began her career in vaudeville and on Broadway before moving into film. Main earned an Academy Award nomination for The Egg and I (1947), which introduced the characters later featured in the popular Ma and Pa Kettle comedy series.
She also appeared in films such as Meet Me in St. Louis (1944), The Harvey Girls (1946), and Dead End (1937).
Robert Livingston – 1321 S Calle Rolph
Robert Livingston (1904–1988), born Robert Edward Randall, was a prolific film actor best known for Westerns and adventure serials.
He played Stony Brooke in the Three Mesquiteers Western series and appeared in serials such as The Lone Ranger (1939) and The Vigilantes Are Coming (1936). Over his career, Livingston appeared in more than 200 films, becoming a familiar face to audiences who enjoyed the Westerns and adventure movies of the 1930s and 1940s.
Continue south toward Sonora Road and turn right. Go one block, then turn right again onto Sagebrush Road.
Oscar Mayer – 1353 Calle Rolph
The name Oscar Mayer is widely associated with the American meatpacking company founded by Oscar F. Mayer. The original tour identifies this address with the Mayer family and describes the residence as an example of the midcentury architecture found in Deepwell.
The home has also been described as a vacation rental, with a design that reflects the neighborhood’s midcentury character and views toward the San Jacinto Mountains.
As you explore, look for the variety of architectural forms along the street. Deepwell’s appeal comes not from one uniform style, but from the combination of Spanish Colonial Revival, Ranch, and modernist influences.
Continue your Palm Springs Bike Tour South to Sonoran Road and turn right. Go one block and turn right again at Sagebrush Road.
Jerry Lewis – 1349 Sagebrush Road
Comedian, actor, and filmmaker Jerry Lewis (1926–2017) became a household name through his partnership with singer Dean Martin. The duo rose to fame in the 1940s and 1950s through nightclub performances, television appearances, and films.
Lewis later developed a successful solo career, starring in and directing comedies such as The Bellboy (1960), Cinderfella (1960) and The Nutty Professor (1963).
He was also widely recognized for his fundraising work with the Muscular Dystrophy Association. His connection to Palm Springs places him among the entertainers who helped establish the desert as a retreat for Hollywood’s creative community.
Turn left at Ocotillo Avenue, then turn left again onto Driftwood Drive.
William Holden – 1323 Driftwood Drive
William Holden (1918–1981) was one of Hollywood’s leading actors and won the Academy Award for Best Actor for Stalag 17 (1953).
His celebrated film career included Sunset Boulevard (1950), The Bridge on the River Kwai (1957), and Network (1976). Holden’s screen presence and versatility made him one of his generation's most respected actors.
His residence is another reminder of the connection between Palm Springs and the stars who sought a quieter life away from Hollywood.
Complete the Deepwell Neighborhood Loop
From Driftwood Drive, turn right onto Deepwell Road and continue west. Deepwell Road becomes South Deepwell Road, which leads back toward East Palm Canyon Drive and the tour’s starting area.
You can also explore the surrounding streets for more examples of the neighborhood’s varied residential architecture. Remember these are private homes: admire the properties from public streets, respect residents’ privacy, and keep driveways and sidewalks clear.
Tips for Your Deepwell Bike Tour
- Ride early or late in the day. Palm Springs can become very hot, especially in summer.
- Bring water and sun protection. Wear a helmet and choose a bike that feels comfortable on neighborhood streets.
- Use a map or GPS. The street-by-street directions make the route easier to follow.
- Watch for traffic. Residential streets are shared with cars, pedestrians, and other cyclists.
- Respect private property. Do not enter yards or driveways or disturb residents while photographing homes.
Explore More of Palm Springs:
- Bike Palm Springs Rentals & Tours
- Palm Springs Big City Loop Bike Tour
- Pedal Through Palm Springs: A Self-Guided Tour of Midcentury Charm
- Nature & Outdoors Guide
- Palm Springs Tours Guide
Frequently Asked Questions
What is the Deepwell Ranch Estates bike tour?
The Deepwell Ranch Estates bike tour is a self-guided route through a historic residential neighborhood in Palm Springs. It highlights the area’s development, architectural styles, and connections to entertainers and other notable figures.
Where does the Deepwell bike tour begin?
The original route begins at the corner of Indian Trail and East Palm Canyon Drive. From there, riders follow Camino Real into the Deepwell neighborhood.
Who lived in Deepwell Ranch Estates?
The tour identifies homes associated with entertainer Ginny Simms, actress Loretta Young, performer Carmen Miranda, actress Marjorie Main, actor Robert Livingston, the Oscar Mayer family, comedian Jerry Lewis, and actor William Holden.
What architectural styles can I see in Deepwell?
Deepwell Ranch Estates includes Spanish Colonial Revival, Ranch, and midcentury modern homes. The mix reflects the neighborhood’s development as Palm Springs grew into a popular residential and resort destination.
Can visitors go inside the historic homes?
The homes on this route are private residences. Visitors should view them from public streets and should not enter the properties unless a home is specifically open to the public through an authorized event or tour.
When is the best time to take the bike tour?
Cooler mornings and late afternoons are generally more comfortable for cycling in Palm Springs. During hot weather, start early, bring plenty of water, and avoid strenuous activity during the hottest part of the day.