In the 19th century — before the first gold strike that led to an influx of would-be prospectors — there wasn't much reason for East Coasters to come out West, which was considered wild, savage and inhospitable.
To those from more "civilized" regions, it might've felt downright prehistoric.
But in 1835, the namesake of the city of Dana Point — then-Harvard student Richard Henry Dana, Jr. — was the exception that became the rule when he set sail on a brig-type tall ship called the "Pilgrim."
Since this was 80 years before the Panama Canal opened, the "Pilgrim" rounded the tip of South America and landed at San Juan Cove — today's Dana Point Harbor, the only safe anchorage between Santa Barbara and San Diego at the time.
Dana deemed the area "romantic" and remarked at its grandeur, publishing a memoir of his sea voyage and time spent at San Juan Cove in 1840 as "Two Years Before the Mast."
The book was a hit — and people arrived in droves to see Dana Point (as it's been officially known since 1989) with their own eyes.
It's far less rugged and far more refined now, but the rich history is there — if you know where to look.
Here are the seven best ways to get to know the historic, literary and watery sides of Orange County's premier surfing and sailing destination — with plenty of breathtaking ocean views, to boot.
1. Del Prado-Lantern District
The area known as The Lantern District is where entrepreneurial types once advertised wares for trade to the ships that came rolling in — by lighting up color-coded lanterns. The most famous of those were the sailors who chucked cowhides (which had been tanned at Mission San Juan Capistrano) off the cliffs, to be retrieved by the Yankee merchant seamen standing below — a.k.a. "hide-droghing."
The lantern motif persists today, through the street names and even lawn ornamentation of the homes in the Lantern District — though the trade does not. You can enter the Lantern District through the arch on Del Prado Avenue, where it splits off from the Pacific Coast Highway.
Just beyond the gateway arch, at 34105 Pacific Coast Highway, you'll find the oldest building in Dana Point — currently vacant, but built as the real estate office for the development efforts of Sidney Woodruff (of Hollywood Sign fame). The Spanish Colonial Revival-style structure features a red terra cotta tile roof and tiled doorways and fountains — under restoration since 2020.
Next, head south to where the Street of the Blue Lantern dead-ends, and you'll find the blufftop pavilion built in the mid-1920s to showcase ocean views for that same planned development. Today, the "Blue Lantern Gazebo" is located at Ken Sampson Overlook Park — named after the former Director of the Orange County Harbors, Beaches and Parks District whose administration spearheaded the construction of Dana Point Harbor. Unfortunately the gazebo has been fenced-off since 2018 — but although you can't enter it, you can get a good look at it.
At the southern terminus of Old Golden Lantern, you'll find another overlook at Compass Point, just above Heritage Park — this one dedicated to Doris Walker, a local historian and founder of the Dana Point Historical Society. Look for a bronze sculpture representing the many features of the area by artist Christopher Pecharka. For more historic sites throughout the Lantern District, see the Dana Point Historical Society's virtual historic walking map.
2. Bluff Top Trail, Lantern District
Although it's technically part of the Lantern District, the Bluff Top Trail — located between Street of the Amber Lantern and Street of the Violet Lantern — is worth its own entry.
This short, historical walk is "ground zero" for where Hollywoodland developer Sidney Woodruff envisioned capturing the romance and adventure of "Two Years Before the Mast" to attract tourists and homebuyers alike to his burgeoning resort community. Real estate developments were booming in the environs north of San Juan Cove in the 1920s — and Woodruff, along with oil heir Edward "Ned" L. Doheny Jr., tried to make a go of it with the ill-fated Dana Point Inn, breaking ground in 1930, the year after the cataclysmic stock market crash of 1929.
Construction on the Inn halted on 1931, leaving it half-finished — and its ruins stood atop the bluff for decades. All that's left now is a bit of the old rock-lined walkways and a set of stone arches that mark the former hotel site like a tombstone.
Walk 0.2 miles (one way) to pass through the arches and read the historical plaque for the Dana Point Inn. There's also a life-size bronze statue of a "hide-drogher" tossing his cowhide down to the ships below — sculpted by F. Benedict Coleman and installed on the walkway in 1990.
3. Doheny House #1, Capistrano Beach
Ned Doheny's contribution to Dana Point should not be underestimated — because it doesn't just end with his family's contribution of 41 acres to create Doheny State Beach in his memory. Today, his legacy can also be found throughout Capistrano Beach, officially part of Dana Point since 1989.
In 1926, Doheny had established The Capistrano Beach Company along with his wife Lucy's brothers, Clark and Warren Smith. The company purchased what had previously been known as San Juan-by-the-Sea — a subdivision established in 1887 by the Pacific Land Improvement Company, a subsidiary of the Santa Fe Railroad Company.
In the three years before his untimely death in 1929, Doheny built dozens of red tile roofed, Spanish Colonial Revival-style "Doheny Houses" along the palisades above the beach. A total of 21 of them survive today, including the first home of the development — Doheny House #1 at 35101 Camino Capistrano (near the intersection of Camino de Estrella, named for Estelle Doheny, Ned's mother).
While Ned was alive, Doheny House #1 (a.k.a. Palisades House #1) served as a gathering place for Doheny family members and their guests. After his tragic death, oil baron Edward L. Doheny Sr. (Ned's father) and his Petroleum Securities Company took over the Capistrano Beach development and the house became the home of Doheny development supervisor Harrison "Harry" Leyden (and subsequently, his son Don and daughter-in-law, local artist Louise Leyden). Its history earned it a spot on the Dana Point historic register in 2001 and made it eligible for the National Register. However, the threat of demolition has loomed over the past several years.
Although Doheny House #1 is not open to the public, you can see its façade from the sidewalk and street — including the historic lamppost out front, which matches those found elsewhere in Capistrano Beach, dating back to its original development. To get a sense of the spectacular ocean vistas visible from its backyard, go next door to the Chloe Luke Overlook, open 6 a.m. to 10 p.m. daily.
4. Pines Park, Capistrano Beach
Today's Pines Park at Camino Capistrano and Doheny Place overlooks the parking lot where Ned Doheny's members-only Capistrano Beach Club once stood as the focal point of his Capistrano Beach development. And while the first thing you might notice at Pines Park is the anachronistic grove of pine trees by the beach, there are intriguing traces of history you can find if you take a closer look.
Originally a private park for residents of the Capistrano Beach palisades — formerly known as "Pines Bluff Park" or "Doheny Pines Park" — it once featured a gazebo, rose garden, wooden walking path and staircase down to the beach (today, Capistrano Beach Park). All of those were located in the lower "bowl" area of the park — known then as "Bowl Gardens" — and unfortunately were razed in the 1960s after decades of neglect (and wood rot). What you can still see today includes the natural "bowl" formation in the bluff (now essentially a dirt patch), an overlook made of stone, old retaining walls, and a rock-lined trail.