2025 Compare Cities Rankings:
Middletown, NY vs Boston, MA

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

#2 Sperlings Skincare Wrinkle Ranking

#2 Best and Worst Airports to make a Connection List

#2 Sleepless Cities 2011

#3 Best Airports to Make a Connection

#3 The Most Single Cities

#4 Best States for LGBTQ Rights

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

#5 Most Difficult Cities to Navigate

#5 Safest Cities for Families with Young Children

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

#6 Best Cities for Teleworking - Extra Large Metro Areas

#7 Most Competitive Private Colleges

#7 The Most (and Least) Gender Imbalanced Cities

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

#8 Best Cities for Seniors 2005

#8 Most Affordable Colleges

#9 Most Irritation Prone Cities

#10 Best US Cities for Seniors 2011

#10 Failure To Lunch

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

#11 Cities on the Edge of Greatness

#12 America's Best Cities for a Healthy Retirement

#13 Most Secure Places to Live in the U.S. (Large Metro Areas)

#13 Best US Cities for Seniors 2011

#14 Healthiest Cities

#14 America’s Least Manly Cities

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

#15 Gloomiest Places in America

#15 Fiscally Fit Cities Report

#16 Most Competitive Public Colleges

#16 Most Romantic Cities for Boomers

#19 Most Comfortable Summer Cities

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

#24 America's Riskiest Online Cities

#25 Best Block Party Places

#25 Stressful Cities 2012

#28 America's Most Playful Cities

#29 Most and Least Risky Places for Identity Theft

#29 Most Popular Cities for the Holidays

#29 Most Energetic Cities

#34 Worst Cities for Respiratory Infections

#34 America's Top Hygge Cities

#35 Americas Manliest Cites 2011

#35 Second Annual “America’s Manliest Cities” Rankings

#35 Best Baseball Cities

#40 2005 Best Places to Live

#42 Hypertension Hot Spots

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

#43 2005 High Gas Prices

#45 Sleep in the City Study

#49 Best Cities for Board Gamers

#50 America’s Manliest Cities

#50 America’s Manliest Sports Cities

#75 Drought-Riskiest Cities

#106 America's Migraine Hot Spots

#234 Best Green Cities

#1 Safest Cities for Families with Young Children

#1 Most Difficult Cities to Navigate

#1 Most Competitive Private Colleges

#2 America's Riskiest Online Cities

#2 Best Cities for Teleworking - Extra Large Metro Areas

#2 Best US Cities for Seniors 2011

#2 Cities on the Edge of Greatness

#3 America’s Least Manly Cities

#4 America's Best and Worst Cities for Crime (Mid-Size Metro Areas)

#4 The Most Single Cities

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

#5 Most Energetic Cities

#6 America's Most Playful Cities

#7 America’s Best Cities for Foodies

#7 Metro Areas with Fastest Rising Income 2020

#8 America's Top Hygge Cities

#8 Best States for LGBTQ Rights

#8 Best Airports to Make a Connection

#8 Sleep in the City Study

#9 Best Cities for Seniors 2005

#9 America's Top Hygge Cities

#10 Gloomiest Places in America

#11 Best Cities for Board Gamers

#11 Healthiest Cities

#12 Best and Worst Cities for Sleep

#12 Most Romantic Cities for Boomers

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

#13 America’s Manliest Sports Cities

#15 Best Baseball Cities

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

#19 Failure To Lunch

#19 2005 High Gas Prices

#20 Most Comfortable Summer Cities

#20 Sleepless Cities 2011

#22 Best Block Party Places

#24 Sperlings Skincare Wrinkle Ranking

#24 The Most (and Least) Gender Imbalanced Cities

#26 Most and Least Risky Places for Identity Theft

#31 Second Annual “America’s Manliest Cities” Rankings

#33 Most Irritation Prone Cities

#35 Stressful Cities 2012

#38 America’s Manliest Cities

#40 Fiscally Fit Cities Report

#41 Worst Cities for Respiratory Infections

#42 Most Popular Cities for the Holidays

#43 Hypertension Hot Spots

#45 Americas Manliest Cites 2011

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

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

#64 Drought-Riskiest Cities

#67 Best Green Cities

#71 2005 Best Places to Live

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

#108 America's Migraine Hot Spots

#121 Best Green Cities

I am a senior looking to move in a nice area in orange county. Thank you kindly for your help.   More

Having lived in Middletown for the last 12 years, I have seen enormous changes. I can only imagine what natives have noted. Firstly, by Manhattan standards apartment  More

Well first off let me say I like, but not love middletown. I am originally from the city. I have been here for one year and my mom has been here for a few. Im a young  More

health care in the country, plenty of jobs, gorgeous architecture, cool neighborhoods, lots of great restaurants, and always something to do. The beautiful coast, the  More

I've lived in/near Boston my whole life almost. It has many pros such as a big city feel, extremely safe, reliable train transportation, great food. However any pro  More

I moved to MA from the country of Georgia in eastern Europe. Then traveled quite a bit in the U.S. Boston definitely has its own flavor. Suburbs offer okay schools,  More