Historic Highway 101 Oceanside, California

20th Anniversary of Historic Highway 101

2018 marked the 20th anniversary since Oceanside helped lead the efforts to designate California’s Highway 101 a historic route. This notable celebration coincides with a renaissance in Oceanside that has witnessed its three-mile stretch of 101 roadway blossom into a treasure trove for visitors seeking a modern-day getaway with a taste of yesteryear. A hip historic hotel, dining venues in classic buildings and attractions that celebrate the past are all part of Oceanside’s “new” vintage 101 vibe.

Nearly 100 years-old, Historic Highway 101 is one of the most beautiful highways in the world and is a vacationer’s delight,” said John Daley of Oceanside Historical Society. “As the birthplace of the movement to establish the highway’s historic designation, Oceanside takes a lot of pride in its Highway 101 experience, which continues to evolve and grow in exciting ways. A day on the 101 in Oceanside includes legendary surf beaches, architectural wonders and of course, endless classic food stops.

A Vintage Vibe Itinerary

For a taste of the past reinvented for modern day fun, here’s how to cruise Oceanside’s 101.

The Fin Hotel
The Fin Hotel
DeWitt Hotel and Masters Automotive Supply circa 1945
DeWitt Hotel circa 1945 (Currently The Fin Hotel)

STAY 101

One of the original hotels on the 101, The Fin Hotel, is now Oceanside’s newest boutique hotel and offers a luxe-modern vacation experience with a distinct retro vibe. The vintage, 27-room property in downtown Oceanside originally opened in 1927 as the Keisker Hotel and after sitting vacant for many years, reopened in Summer 2018 following an extensive restoration that preserved features such as the multi-colored, mosaic tile flooring in the lobby, a grand wooden-railed staircase and tiffany windows surrounding the first floor.

Guests enjoy a convenient location just a few blocks to the beach and in the heart of downtown near craft breweries, restaurants and entertainment. What’s more, with the Oceanside Transit Center within easy walking distance, guests can go truly old-school and opt to travel by train to their getaway at The Fin Hotel.


MORE: Explore Southern California by Train

Local Tap House Pecan Crusted Goat Cheese Salad

EAT 101

Oceanside’s recent culinary resurgence has welcomed a host of landmark dining venues housed in historic buildings reinvented for modern living.

Masters Kitchen and Cocktail Bar

Masters Kitchen and Cocktail is a popular spot for craft cocktails and farm-to-table inspired lunch and dinner menus housed in an historic industrial space that was once a drag car shop.

Blade 1936 Restaurant

Blade 1936, a contemporary Italian restaurant, is slated to open in late 2018 in what was home to one of the city’s earliest newspapers, The Blade-Tribune, from 1936 until the 1960s. The restaurant has taken steps to preserve the building, which was designed by famed San Diego architect Irving Gill, beginning with uncovering the original façade to reveal concrete stamping of the building’s original name.

Oceanside Murals 101 Cafe

101 Café enjoys the distinction as the oldest continuously operating café along the 101 and is a go-to spot for hand scooped milkshakes and 50s diner-style delights.

Le Citron Oceanside

Le Citron plating delicious menu items with a global influence.

Family Bike Wheel Fun Rentals on the Strand

PLAY 101

Oceanside’s recent culinary resurgence has welcomed a host of landmark dining venues housed in historic buildings reinvented for modern living.

Downtown Oceanside History Walk

Visitors can experience Oceanside’s history through numerous activities along the highway’s route. Oceanside Historical Society offers seasonal guided walking tours and maps for self-guided tours that include noteworthy architectural sights including the Oceanside Pier and Junior Seau Beach Amphitheater, Top Gun House, Roberts Cottages, Civic Center Library and Star Theater.

Sunset Market

At the Thursday evening Sunset Market in downtown Oceanside, which is a popular year-round activity due to the nearly 200 gourmet food vendors, there will be a special booth featuring rare photos of Highway 101 for visitors to enjoy during fall months.

South O Walkabout

South O, a quaint Coast Highway neighborhood and shopping district, offers an Oceanside twist on retro 101 with unique maker spaces, vintage-inspired shops and a variety of popular local dining options including a prohibition-era inspired speakeasy.

Oceanside Museum of Art

The California Surf Museum is a great stop for visitors seeking a glimpse into the history of Southern California’s surf culture, while the Oceanside Museum of Art, which played a key factor in Oceanside being named one of just 14 California Cultural Districts by the California Arts Council in 2017, offers visitors a great example of 1929 Irving Gill architecture as well as a renowned venue for discovering cultural and contemporary art.

Bank of Italy on Hill Street at 2nd Street | Oceanside Historical Society
Bank of Italy on Hill Street at 2nd Street | Oceanside Historical Society
Graham's Drive-In at Seventh and Hill Street (1957) | Oceanside Historical Society
Graham's Drive-In at Seventh and Hill Street (1957) | Oceanside Historical Society


A favorite drive for locals and visitors alike, the Historic Highway 101 is a 935-mile highway that runs the length of California and was once the main street of many California cities and towns along the coast until Interstate 5 was built, becoming the route of choice for drivers.

In 1998, Oceanside historian John Daley met with local legislators to resurrect replicas of the old Highway 101 signs showcasing the routes historical significance.

Initiated by then State Assemblyman William Morrow and co-authored by the late State Senator William Craven, both Oceanside Republicans, the 1998 legislation recognized that the route was one of the first in the state highway system, designated by the Bureau of Highways in 1896 and adopted formally in 1909. The federal designation was added in 1925.

Daley, interviewed near the Historic Route 101 sign at North Coast Highway (formerly Hill Street) and Mission Ave (Second Street once upon a time), said his curiosity about the road was piqued by a transportation report given to the city’s Historic Preservation Commission by former city Senior Planner Rita Baker. The report was written by the late Kathleen Flanigan, a well-respected historical researcher in San Diego County.

He noted when the city was incorporated in 1988, it was important that the roadway run relatively near the railroad tracks. Local trucks took goods off of the trains.
Just as it was called Hill Street or Coast Highway in Oceanside, other North County cities have had their own names for the route: Camino Del Mar in Del Mar, once First Street in Encinitas, and Carlsbad Boulevard in Carlsbad.

They jumped on the historical-route designation bandwagon with Oceanside. A Highway 101 Association was formed. Peter Norby, then executive director of the Downtown Encinitas Mainstreet Association, was a particularly enthusiastic supporter. “It was an important part of our history, of our economic development,” said Daley.

… But he said the real impetus was Flanigan’s transportation report. The route through town was THE highway linking Los Angeles, Orange and San Diego counties along the coast until a bypass was opened in 1953 – and later I-5 was built. (Sherman, Lola. “The 20th Anniversary of Historic Highway 101” Discover Downtown. Fall 2018: 4-6. Print.)

In San Diego, the route links a string of charming beach communities from Oceanside, where it is also known as Coast Highway, to La Jolla and hugs the Pacific Ocean providing a taste of Southern California’s fervent surf culture.

Although no longer a formal Highway Route, in 1998, the City of Oceanside was instrumental in securing a historic designation for the roadway, so that it would be recognized for its outstanding natural, historic, cultural and scenic qualities as well as its significant contribution to the development of California in the 20th century. Today, remaining portions of the original US Highway Route 101 are recognized by highway markers and signs that highlight the special designation.

Top Gun / Grave's House Historical Oceanside

Downtown Oceanside Historic Landmarks

Shopping in Oceanside, CA - Girls Getaway - Captain's Helm - South O

Thirft Store Shopping

Star Theatre Mural

Murals and Street Art