Food & Drink

East Side Eatery’s Eclectic Breakfast Menu and Award-Winning Chili

Pleasure Point spot has racked up awards for both its chili and chowder

East Side Eatery diners have been taking advantage of the patio option during the pandemic. PHOTO: TARMO HANNULA

East Side Eatery, a cornerstone of the Pleasure Point dining scene, is open seven days a week for lunch and dinner, and for breakfast Friday-Sunday.

Formerly a Google executive chef, Derek Rupp became the chef and owner 10 years ago. He said he wanted to be a bigger part of the community and do what he loves here in Santa Cruz, and to be more involved with his kids as they grew up. He spoke to GT about his restaurant’s menu and award-winning dishes.

How has breakfast/brunch been going, and what are some menu highlights?

DEREK RUPP: With all the Covid stuff, it has been our hardest-hit sector of business. We have a very eclectic breakfast menu and serve food from all over the world, such as nasi goreng, a fried rice dish from Bali. It’s like their national breakfast dish, and is basically fried rice with an egg and an Indonesian-style ketchup. And we serve chilaquiles, which are homemade tortilla chips sautéed with chili sauce and eggs. We do traditional eggs benedict, too.

What are some of the most popular items on the dinner menu?

Our fish tacos are outstanding. They have seared Alaskan cod with jalapeño lime sauce, macerated green cabbage, chipotle mayo, and fresh salsa on corn tortillas. We also have a hickory smoked tri-tip sandwich with house barbeque sauce, romaine lettuce, tomato, and fried onions for crunch. We have great salads on the lighter side; my favorite is the Thai Crunch. It has napa cabbage, sunflower sprouts, red bell peppers, and carrots, tossed with a Thai peanut ginger dressing. It’s a vegetarian dish but can be served with a protein. My favorite to add is prawns.

What makes your award-winning chili and clam chowder so special?

My chowder recipe pays a lot of respect to what Boston clam chowder should be. It’s very traditional—in New England they got it right, so we try and stay true to that. We’ve won four times for best chowder at the Santa Cruz Boardwalk Chowder Cook-Off. Our chili is a meat chili and has no beans in the traditional Texas style. We get our fresh peppers from Coke, a local organic farm, and our dried peppers come straight from New Mexico. We won the last five years in a row, both the people’s choice and judge’s choice, at the Santa Cruz Boardwalk Chili Cook-Off.

800 41st Ave., Santa Cruz. 831-431-6058,

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