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Middletown, NY

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A picturesque town in Orange County's Hudson Valley with beautiful street-level views of the wooded Shawangauk foothills, Middletown is a traditional, old rail-stop community. The town sprung up near the Wallkill River and with the railroad’s arrival, Middletown boomed. Most businesses from that period are long gone. Rocky economic times hit home in Middletown in the 1970s and ‘80s as they did in many of the Hudson Valley's small communities. This little city has recovered and continues to thrive.

Middletown Apartments


Vista Point
Beds: 1-3
Baths: 1-2


Patricia Gardens
Beds: 1-3
Baths: 1-1.5


Hudson View Estates
Beds: 1-3
Baths: 1


eaves Nanuet
Beds: 1-3
Baths: 1-2


Imperial Gardens
Beds: 1-3
Baths: 1-1.5


New Paltz Gardens
Beds: 1-2
Baths: 1

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Getting Around in Middletown, NY

Walk Score®
"Somewhat Walkable"
Transit Score®
The average commuter time in Middletown is:
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SUNY Orange

Orange County Community College, also known as SUNY Orange, opened its doors in Middletown in 1950. Two associate degree programs are offered through the Middletown campus, and professional certification and training programs for adult learners are also available. The college's campus, which is located in Middletown's southwest side, is the site of community interest events as well, including expos and trade shows. Notably, the original home of the college was one of modern Middletown's treasured historic landmarks, the Web Horton House, a mansion that still stands on the campus today, and serves primarily as the administration building for the college.

Brian's Backyard Barb

Brian's may not look like much from the outside, housed in a rather nondescript building off Route 211 northeast of Middletown, but for blues lovers and anyone that craves traditional, Southern-style barbecue, this is the perfect Friday or Saturday night spot. Brian's Backyard Barbecue and Blues has live performances all weekend and open jams Mondays and Wednesdays. Other activities and nightly specials bring visitors in on weeknights as well. A selection of craft beers and the full menu that includes a wide selection of other Deep South cuisine, in addition to traditional barbecue, makes Brian's a popular dinner spot, too.

Paramount Theatre

Middletown's Historic Paramount Theatre is a downtown landmark, dating to 1930. For nearly four decades, the Paramount was a date night and family outing destination, but during the height of the Hudson Valley's economic hardships, the Paramount also fell on hard times and closed its doors in the late 1970s. The theater sat unused for many years, but downtown revitalization efforts and Middletown's arts enrichment initiatives led to major renovations. The Paramount reopened in 2010, and is now a venue for live music and stage plays as well as a theater capable of screening both classic and contemporary films.