Best Milkshakes In The South Bay

November 1, 2013 7:00 AM

(credit: DANIEL GARCIA/AFP/Getty Images)

The word milkshake alone can bring a smile to your lips, and actually tasting one can make you laugh out loud, or at least feel pretty happy. Lucky for us the South Bay has no shortage of these cool treats to perk us up when the going gets bumpy. Cruise on over to any one of these five South Bay spots for the best milkshakes around.

City Diner
2951 Monterey Road
San Jose, CA 95111
(408) 269-5490

In honor of the 66 stops en route from Santa Monica to Chicago, City Diner wants you to “enjoy a nostalgic milkshake while you’re traveling Route 66.” In honor of that journey City Diner offers milkshakes in 66 flavors, including classics vanilla, chocolate and strawberry, plus combos such as strawberry banana or chocolate cherry, and some different options like banana Oreo malt or chocolate peanut butterscotch, $4.69-$5.69 depending on flavor. City Diner also serves an extensive menu of diner favorites for breakfast, lunch and dinner. See the website for more details.

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(credit: Palo Alto Creamery)

Palo Alto Creamery 
566 Emerson St.
Palo Alto, CA 94301
(650) 323-3131

Five generations of customers must be right. Since opening in 1923, Palo Alto Creamery has honored its philosophy of “simple food, done well.” That longtime philosophy definitely refers to its milkshakes too as the Palo Alto Creamery’s breakfast served-all-day items, dinner menu and fountain treats the shop boasts are “made by authentic soda jerks” continue to draw fans of all ages. Shakes, $6.35, can be amped up with a variety of additions such as peanut butter, banana, dates, hot fudge and more for 75 cents or 95 cents extra, plus there is a choice of over 21 flavors including seasonal options too. What’s not to love about this place?

Peggy Sue’s
29 N. San Pedro St.
San Jose, CA 95113
(408) 298-6750

Peggy Sue’s owners, brothers Marcello and Armando America, came to the restaurant business as kids as their restaurateur parents instilled a love of the family business in them. With a ton of classic and updated 50s restaurant favorites, including classic milkshakes, floats and sundaes, this spot is open until midnight and later on Friday and Saturday. Classic shakes are made with hand-dipped vanilla ice cream and available in eight flavors including pineapple, mocha, banana and peanut butter, in addition to more traditional favorites like strawberry, chocolate and vanilla at $3.99 each. Make it a malt or add a flavor for 40 cents more.

Related: Cheap Diners Around San Francisco

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(credit: Peninsula Creamery

Peninsula Creamery 
900 High St.
Palo Alto, CA 94301
(650) 323-3175

A family-owned business for more than 85 years, the “Pen,” as locals know it, is a breakfast, lunch and milkshake shop that has operated a popular 50s-style soda fountain since 1936. With a menu of longtime fountain grill breakfast and lunch favorites, the Pen remains a well-liked destination, especially for its hand-scooped milkshakes ($5.25) made with high-quality ice cream that some fans describe as “unforgettable.”

Kirk’s Steakburgers
2388 S. Bascom Ave.
Campbell, CA 95008
(408) 371-3565

While Kirk’s is known for its steak burgers cooked over charcoal, the same way founders Bill and Kirk cooked them in 1948 when Kirk’s first opened, the place also has some of the best milkshakes in town. Take your pick of traditional vanilla, chocolate or strawberry milkshakes, regular/$4 or Torani shakes in more adventurous flavors such as banana, butter rum, root beer and raspberry, to name a few, $4.10. Both shake types are also available in malt or combo at slightly higher prices. Kirk’s has expanded to four locations with customer loyalty behind that awesome growth. Visit the website for additional menu and location information.

Related: Best Cold Treats In North Bay

Melanie Graysmith is a writer, artist and educator based in San Francisco. She writes on adult education, art and lifestyle topics, and enjoys writing short stories and poetry. She is also a member of an independent filmmaking group. Her work can be found at

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