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Montgomery, Town of

Montgomery, “Transportation Hub of the Northeast”

One of the more largely populated towns in Orange County, New York, Montgomery sits on the border of Ulster County. The town was once known as the “transportation hub of the northeast,” as the Wallkill Valley Railroad, plus the New York, New Haven and Hartford Railroad ran through the town. These railways provided transfer hubs for freight and passengers from all over the area. While transportation and travel by roadways is more widely used today, train fans will be impressed with the area’s history. 

In the early days, Montgomery was also dependent on farming and textile businesses. Most of the area is like visiting a museum, as many buildings in downtown are on the National Register of Historic Places. The Montgomery Village Museum is dedicated to the history of the area; architecture fans travel to the town to see Greek revival buildings from the 1800s, such as the Borland House, a bed and breakfast built in Greek revival style of the 1830s.  

The Orange County Farmer’s Museum is a fun place to visit with children and private guided tours can be arranged. In addition to the exhibits, special events include lectures, demonstrations and tractor pulls.

Another favorite, Ms. Claire’s Music Cupboard, offers music lessons and classes for children from a Montessori perspective. Mommy and Me classes present opportunities to sing, dance, play instruments and make great memories with your kids. There is a variety of cafes and bakeries in the area that make for a morning or afternoon outing by grabbing a bite to eat for lunch or a sweet treat before or after class. 

The Thomas Bull Memorial Park offers playgrounds, picnic areas, ball fields, walking trails, basketball courts and more. A highlight is Sally’s Playground, which was created to be accessible to children with disabilities. More accessible equipment was added in 2017. 

Population: 23,664
Median Home Value: $230,500

County: Orange, NY
Latitude: 41.52090012
Longitude: -74.25443459

110 Bracken Rd.
Montgomery, NY 12549


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