Unless you hop on the train and take a 40 minute express to Manhattan, you're going to be bar hopping in downtown Stamford. There are many bars all next to each other if that's your thing, there are also a couple of movie theaters as well as a performing arts center right downtown. If you stay downtown, everything is within walking distance. The train station is also within walking distance from downtown and will take you straight to Grand Central Station. If you rent a car, you can drive north and visit the Stamford Nature Center or take a beautiful drive into Westchester New York and follow Route 22 north for a beautiful drive in the country. You can also drive one town over to the west and visit Greenwich, CT and walk along Greenwich Avenue and maybe spot a local celebrity.