Must-Visit Destinations in Montgomery, NY

Nestled along the serene Wallkill River, Montgomery is a farming and milling town in the northern section of Orange County, New York. Originally known as Ward’s Bridge, the town is named in honor of Richard Montgomery, who served as a brigadier-general in the Continental Army during the American Revolution.

Montgomery has plenty of great attractions and destinations catering to a wide variety of interests. If you’re searching for some of the best spots to visit, here are a few suggestions:


Borland House Inn

If you’d like to steep yourself in Montgomery’s fascinating historic architecture, book an accommodation at the Borland House, a bed and breakfast in a Greek Revival home built in 1789. Located in the heart of the historic Village of Montgomery, Borland House is a short walk away from some of the village’s top-rated restaurants and pubs.

Guests will be able to choose from five distinct rooms including the Montgomery, the home’s original master bedroom, and two rooms which form the Artists’ Annex. For culinary enthusiasts, all rooms booked at the Borland House includes a complete farm-to-table breakfast featuring items from their seasonal menu. They also offer cooking classes, a venue for special events, and a private five-course tasting menu.

Guests can book a table at their restaurant even if they’re not staying overnight.


The Historic Districts of Union Street-Academy Hill and Bridge Street

One of the most unique aspects of Montgomery is its gorgeous architecture. Most parts of its downtown area are included on the National Register of Historic Places and are divided into two districts: Union Street-Academy Hill and Bridge Street.

Union Street-Academy Hill encompasses over 300 acres and includes more than 80 early to mid-19th century structures representing Greek Revival, Federal, and English Baroque architecture. The smaller Bridge Street, on the other hand, is home to some of the oldest buildings in town.

One of the many highlights is the Montgomery Academy building, which was the fourth school that was incorporated under the New York State Board of Regents. Another notable venue is Wesley Hall, a former Methodist Church which now houses the Montgomery Village Museum.


Thomas Bull Memorial Park

If you’re looking forward to spending time outdoors, soaking in relaxing views, and enjoying a fun-filled day with the family, Thomas Bull Memorial Park is the perfect place to visit.

The park is the second-largest facility in the county parks system and offers a wide variety of recreational opportunities for visitors of all ages. Encompassing more than 700 acres, the park features a variety of amenities including tennis courts, an 18-hole golf course and driving range, playgrounds, a dog park, picnic areas, fishing facilities, volleyball courts, a winter sports area, and more.

One of the park’s most notable features is the Orange County Arboretum, a 35-acre facility with raised gardens, cascading water features, and a diverse assortment of trees, plants, and shrubs.