Middletown (New York)
Middletown is in Orange County.
Much of the area around Middletown -- including the Town of Wallkill, which completely surrounds Middletown -- has a Middletown mailing address. Much of what people typically think of as being in "Middletown" is in the Town of Wallkill, including the well-known Galleria mall, and the busy Route 211 retail strip.
The City of Middletown is about four square miles with about 30,000 people. It's a former industrial/railroad town, like many cities in upstate New York, and has the gritty, older, post-industrial look and feel of many other upstate cities.
Wallkill used to be a farm town, but has gone suburban and commercial in a big way over the past few decades. It's a town of hamlets. Mechanicstown, just east of Middletown on East Main Street, feels like a slightly more spaced-out extension of the city. Route 211 is the commercial center, where most of the stores and restaurants and the Galleria are. Scotchtown and Silver Lake are residential areas north of Route 211. Circleville and Howells are rural hamlets.
By car: Interstate 84 and New York state Route 17 intersect in the Town of Wallkill, near the Galleria and Route 211.
By train: New Jersey Transit's Port Jervis line, which runs from Port Jervis, N.Y. east to Hoboken, N.J., has a stop in the Town of Wallkill next to the Galleria.
By bus: Short Line buses stop on Railroad Avenue in Middletown.
Traffic can be heavy on Route 211 and around the highways.
There is a local bus system that operates Monday-Friday from 7:00am to 5:30pm. Otherwise, you have to walk, drive, or bicycle to get around. 
The Paramount Theatre: An old theater on South Street; they show older and more specialty movies sometimes.
The Galleria: In the Town of Wallkill, near the Route 84/17 interchange. One of the biggest malls in New York, with dozens and dozens of stores.
North Street is lined with Hispanic-owned businesses -- a grocery store; convenience stores; Mexican restaurants.
Middletown is full of restaurants; the city has tried to advertise Main Street as "Restaurant Row." Just on Main Street and North Street you can find haute cuisine, pizza places, a hot dog restaurant, a couple convenience store/delis to get a sandwich, Italian, Chinese, Puerto Rican, Mexican, Caribbean, sushi and soul food.
A few notable restaurants in the city:
Tony Boffa's: 75 Railroad Avenue. A popular Italian restaurant, the last left in the area that used to be Middletown's "Little Italy." The other old family-owned places have mostly closed.
The Old Erie: 7 West Main St. Italian food; there is also a bar, which can get busy on weekend nights. Owned by Mayor Joe DeStefano's family; there's still a sign on the building saying "DeStefano's."
John's at Arthur Avenue: Also on West Main, a couple doors down from the Old Erie. Large, New York-style slices of pizza, and other
Osake: A sushi and Japanese restaurant, also on West Main, next to John's. The owners also own the Asian 211 Bistro, on Route 211.
Taco Factory: 40 North St. A Mexican restaurant. Tacos are $1.25 each.
The Town of Wallkill has even more restaurants, all over the town, but with a concentration on the shopping strip on Route 211 East. Cheeseburger in Paradise, at 340 Route 211, is one local favorite. Typical American food -- burgers, sandwiches, wings -- with a Hawaiian/tiki-bar atmosphere. You can also find all the chain restaurants you would expect. Blue Chip Burger, at 368 East Main St., is a smaller place with burgers and a slightly offbeat beer selection. (You can get cans of Narragansett, not an easy beer to find in New York.)
There are a number of bars within walking distance in Middletown's downtown. Prices are pretty good, as they are elsewhere in upstate New York, and drink specials are frequent. The atmosphere at most places is pretty laid-back and down-to-earth.
The Old Erie
The Smith: Across the street from the Old Erie, on West Main.
The Empty Bottle, also on West Main Street, a couple doors down from the Smith.
Players: On John Street. Blue-collar atmosphere; draws a slightly older and more traditional crowd than the other bars in the Main Street area.
Poor Bobby's Hard Times Tavern: On Center Street.
Divass. At 90 North St. Opened recently (fall 2012); calls itself a sports bar, caters to a mostly Hispanic crowd.
The Switch Inn is a bit further up on East Main Street; they serve food, too.
There are also several neighborhood bars: The Bullpen on Beattie Avenue, The Pit Stop on Cottage Street and G's Westgate Inn on West Main Street.
There are many more bars in the Town of Wallkill, and many of the chain restaurants have bars at them. The one at Buffalo Wild Wings, at the corner of 211 and Tower Drive, is pretty popular, as is Cheeseburger in Paradise. Bierfest is an Austrian restaurant on Schutt Road with 20 German beers on tap. The bar at the Chinese restaurant You You on Route 211 is small, but gets fairly busy on weekend nights.
Middletown does have its share of crime, and is dealing with an increase in robberies and burglaries, but the only really dangerous areas are ones that visitors wouldn't have much reason to go to. The whole city's generally safe to walk around during the day. Much of North Street -- the whole street north of, roughly, Roberts Street -- can be dodgy at night, especially in the Park Circle area, but a visitor won't have much reason to go there at night. There are some convenience stores and takeout places up there, but not much that would draw a visitor away from the offerings on Main Street.
Linden Avenue is one of the city's higher-crime areas, and the streets off of Academy Avenue are pretty rough too, but these areas are both completely residential.
The area around the bus station and taxi stand on Railroad Avenue attracts its share of panhandlers and undesirable characters.
The Town of Wallkill has some of the same problems as the City of Middletown, but less so, generally speaking. The Patio Road and Meadows neighborhoods have their share of problems with drug use and bored teenagers, but these areas are all-residential.