2025 Compare Cities Rankings:
Sierra Madre, CA vs Cupertino, CA

#2 Most Comfortable Summer Cities

#2 Top 10 Cities to Beat the Heat

#43 Best Cities for Board Gamers

#47 Gloomiest Places in America

#50 America's Top Hygge Cities

#1 Healthiest Cities

#1 Best Cities for Teleworking - Large Metro Areas

#1 Metro Areas with Fastest Rising Income 2020

#3 Best-Rested Cities 2011

#4 Most Comfortable Summer Cities

#4 Most and Least Risky Places for Identity Theft

#4 Top 10 Cities to Beat the Heat

#5 The Most (and Least) Gender Imbalanced Cities

#6 Most Competitive Private Colleges

#7 Most Secure Large Cities in the U.S.

#8 America's Best and Worst Cities for Crime (Large Metro Areas)

#17 Best Baseball Cities

#20 America's Riskiest Online Cities

#24 High Gas Prices - Which Cities are Hit the Hardest?

#32 Gloomiest Places in America

#36 Best and Worst Cities for Sleep

#36 Best Airports to Make a Connection

#38 Best Cities for Seniors 2005

#38 Fiscally Fit Cities Report

#39 America’s Best (and Worst) Cities for Dating

#40 The Most Single Cities

#42 Failure To Lunch

#44 America's Top Hygge Cities

#45 Stressful Cities 2012

#48 Drought-Riskiest Cities

#48 Best Cities for Board Gamers

#48 Sleepless Cities 2011

#50 Wrinkle Ranking Cities Most at Risk for Skin Damage by 2040

#51 2005 High Gas Prices

#56 America's Most (and Least) Stressful Cities (100 Largest Metro Areas)

#73 Most Popular Cities for the Holidays

#168 2005 Best Places to Live

#178 Best Green Cities

Sierra Madre is a great place to live if you enjoy a small town atmosphere while being close to the vibrancy of a big city. It has nice restaurants, boutique shops and  More

Sierra Madre is still much a 1950's town. We still help out our neighbors, we have block parties to get acquained with new neighbors, and it's just a happy, friendly  More

I love this city. Cupertino has everything to offer. We have the best schools, weather, health care, and everything is close by. Absolutely everything is here.   More

I’ve lived here for 24 years. Cupertino is totally convenient. Literally library, parks, grocery stores, all shopping, bakery’s, restaurants, all within walking  More

I look at the pros and cons listed here about Cupertino and I just laugh. I’ve lived here for 21 years. Here’s what I can tell you.The pros:-The weather is good year  More