Age: 176 years old
Brotherhood Winery claims to be America’s oldest winery, having managed to stay alive during Prohibition because it sold sacramental wine (thank God for loopholes!). Today you can take a tour of the old cellars and sample the award-winning wines on a trip up to the Hudson Valley, where you can visit other younger, less-impressive wineries, too.
Oldest prison: Auburn Correctional Facility
Age: 199 years old
Auburn was the second correctional facility built in New York, but it’s the oldest one still standing. Since it opened its creepy doors some Shawshank-level shit has gone down behind those walls, plus it’s also somewhat of a trendsetter in the incarceration industry: the very first electric chair execution took place at Auburn in 1890. The prison also became well known for its disciplinary system which included corporal punishment (an early form of waterboarding it called "shower baths") and putting its inmates to work to make money for the state -- those license plates have to be made somewhere! The "Auburn System" became a thing copied by prisons across the country. It made history again recently because it was the site of the New York prison system’s first same-sex marriage when a former inmate married a current inmate.