The street is too wide and the sidewalk is too narrow. More to the point, it is empty, even on a beautiful Saturday afternoon. The only walking on Main Street is from one's car to the store and back. Although it is an eclectic mix of stores and restaurants, it lacks physically intimate spaces suitable for hanging out. Instead the only people hanging out there are outpatients from the nearby mental asylum at the south end. If they interact with passerby at all it is only to ask for money. At the north end Main Street features less upscale business and more "urban blight" in the form of alcoholics and drug addicts loitering. Although Main Street is not scary to walk down, it is creepy because it is so empty, and it does not always feel entirely safe either.

Main Street lacks human scale in that it is forbiddingly wide to cross, and traffic moves fairly fast. It features an indoor mall which sucks pedestrians off the street. The streetwall is frequently broken by driveways and parking lots. The new buildings are only one story high, which is inappropriate because the street is so wide and the older buildings are taller. It also means that what could be low income housing or office space above stores does not exist. This contributes to the desolation. There is a lot of surface parking just off Main Street in either direction, and yet on Saturday nights when everyone goes out to eat it seems that there is never enough. The City of Middletown should have invested in building above ground garages or underground lots, which would have provided more parking and done less damage to the street. Along Main Street the bank buildings and the new police station put blank walls along the street.

"Undesirables" and vehicles both dominate the space. There is no one in charge in the sense that there are no unofficial "block mayors" who spend time on the street getting to know its denizens, and keeping an eye out for people. The city has designed the streets to speed up traffic rather than accommodate pedestrians. Spear Park, a pathetic ugly triangle of concrete at the south end of Main Street, only attracts panhandlers. Litter is not a problem because there are no pedestrians around to litter. The space does not feel excessively dangerous, but it does feel unwelcoming. South Green, which was once the unofficial town square, was chopped in half and effectively ruined to ease the flow of traffic.

There are no places to sit of any kind on Main Street, no public benches, no steps or ledges. One does not stop while on Main Street, one simply walks to wherever they are going, and then leaves. There are no trees, so rather than feeling intimate, Main Street feels vast and empty. There are no gathering points, just stores.

There is nothing much worth showing off about Main Street, locals might take relatives there as it has some decent stores and restaurants, and is, unfortunately the prettiest commercial street Middletown has to offer. Although people would meet their friends at specific restaurants or bars there, one would not meet on Main Street itself, as there is no place suitable for that purpose. People go to the stores and restaurants of Main Street alone as well as in groups, but not many people go to Main Street in and of itself. I personally would not smile or make eye contact with someone I passed on Main Street as they would almost certainly take advantage of that opportunity to ask me for money.

Despite its physical shortcomings, photographs and memories from a long time ago show that Main Street was once much more successful. It had traditional New England architecture, including civic buildings with columns and steps that glorified the public realm. They have all been torn down, during the "urban redevelopment" period from the 1960's to the 1980's. The new court building and city hall were moved off Main Street. The neighborhood adjacent to Main Street was mostly torn down and replaced with parking lots to serve the new city hall and courthouse, and the new strip mall behind Main Street. The high school was moved out of the vicinity. All of these things conspired to take away the communities that used to walk to Main Street and spend time and money there. This was Main Street's death as a neighborhood street. In recent years it has to a certain extent repositioned itself as a regional center for dining out and entertainment, with some success. While this has improved the options of what to do on Main Street for those who frequent it, the new customers come from farther away, all by driving, and so Main Street has not experienced a commensurate rebirth as a center for community.