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Middletown, City of

Middletown brings together history, nature and entertainment

Located in the Hudson Valley region of Orange County, New York, Middletown is easily accessible to the Wallkill River and foothills of the Shawangunk Mountains. The area is rich in beautiful outdoor scenery to explore and play in, including at Highland Lakes State Park where more than 3,000 acres of woods and lakes makes the perfect setting for hiking, horseback riding, fishing, biking, picnicking and more. There’s also the Hunter Farms Preserve whose “Tadpole Trail” is great for the youngest hikers and the Wallkill Golf Club for golf enthusiasts. 

Middletown’s historic Paramount Theatre is a great example of art deco style from the 1930s. The working theatre showcases a variety of films and performances and younger patrons love posing for photos around the theatre.

History buffs will want to check out the museum at the Historical Society Middletown, a historic landmark building with all sorts of information on the area’s history. The First Congregational Church is another historic landmark.

Middletown has the second-largest shopping mall in the Hudson Valley area, the Galleria at Crystal Run. It’s quite the destination whose 100-plus tenants mean visitors can find just about anything they might want to buy. The mall also features food courts, sit-down restaurants, a movie theatre, an escape room, bowling, nightlife and art galleries. Spend a morning, afternoon, evening or the whole day there. There’s even a gym for adults, a spa to get massages, manicures and pedicures and a huge indoor playground for kids. 

Enjoy the town’s summer entertainment, too. The Orange County Fair takes place in Middletown in late July with concerts, roller derby and rides. This also is when the Orange County Fair Speedway opens, with races continuing through October. Not bad for what’s said to be the oldest continuously operating racing surface in the world.  

Population: 27,729
Median Home Value: $185,300

County: Orange, NY
Latitude: 41.44587214
Longitude: -74.45787634

16 James St.
Middletown, NY 10940


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