A Visitor's Guide to Washingtonville, New York

Washingtonville sits in the heart of Orange County, New York, tucked into the rolling hills of the Hudson Valley. This small village is part of the Town of Blooming Grove and is home to about 5,700 people. It is less than an hour and a half from New York City, which makes it an easy day trip or a quiet place to call home. Washingtonville blends small town charm with a rich history, and it has become known for its wineries, its historic buildings, and its friendly Main Street.

The History Behind the Name

Washingtonville was first settled in 1731. Back then, the area was known as Matthews Field, named after Vincent Matthews, one of the first European settlers to arrive in the region. Long before that, the land was home to an Indigenous inhabitant named Moringamus, whose home once stood near where a local gas plant sits today.

By the early 1800s, the settlement had grown into a small community of about nine houses and became known as Little York. In 1809, a boot and shoemaker named John Jaques opened a shop there. Thirty years later, in 1839, Jaques started what would become Brotherhood Winery. That winery still operates today and holds the title of the oldest continuously operating winery in the United States.

The village later took on the name Washingtonville in honor of George Washington. Growth picked up in 1850 when the New York, Lake Erie and Western Railway built a branch through the area. Dairy farming became a major part of the local economy, with creameries, markets, and small shops filling the village center. Washingtonville officially became an incorporated village in 1895.

One name that comes up often in local history is Moffat. Samuel Moffat built a trading post on the village square in 1811. His son, David Moffat, later built the Moffat Library in 1887 as a tribute to his mother. That library still stands today and remains a point of pride for the community.

Landmarks Worth Visiting

Washingtonville and the surrounding area offer a good mix of history and nature. Brotherhood Winery is the most well known stop in the village. Visitors can take a cellar tour, sample wine, and browse a gift shop filled with local jams and treats. The property's nineteenth century architecture gives the tour extra character.

Just outside the village, history lovers can visit Washington's Headquarters State Historic Site. This spot marks where George Washington stayed during part of the Revolutionary War, and the grounds include a monument with sweeping views of the Hudson River. It is a peaceful place to walk around, even if you only have a short amount of time.

Main Street itself is worth a slow stroll. Many of the storefronts date back to the 1800s, and the street is lined with brick buildings, small art studios, and churches with tall white steeples. St. Mary's Church is known for its stained glass windows, and the First Presbyterian Church has a long history dating back to 1841.

For outdoor time, Carnwath Farms Park offers walking trails, including one that follows Wappinger Creek. Mays Field and Vern Allen Park are popular gathering spots for local families, with youth sports, concerts, and community events held throughout the year.

Where to Eat in Washingtonville

Washingtonville has a dining scene that punches above its weight for a village this size. The 1839 Restaurant and Bar sits right on the grounds of Brotherhood Winery and offers a rustic setting with a menu built around American classics and a strong wine list.

Amada's Kitchen is another local favorite, known for empanadas, tacos, and pernil served in a casual, welcoming setting. If you are in the mood for Italian food, Positano Restaurant and Pizzeria is a popular choice, and locals often mention the friendly, hands on service from the owners. Greek Brothers Grill offers a solid Mediterranean menu, while Kam Fung Chinese Restaurant and Tacos Y Mas round out the village's mix of international flavors.

For something quick, T and M II Go is a go to spot for deli sandwiches and catering. Pizza lovers in town tend to have strong opinions about their favorite local shop, and several small pizzerias around Main Street have loyal followings, especially for their garlic knots and specialty slices.

A Note on Staying Safe

Washingtonville's wineries and restaurants make it a popular spot for get togethers, celebrations, and weekend outings. With that in mind, it is worth thinking ahead about how you plan to get home after a day of wine tasting or dinner out. Driving under the influence carries serious legal consequences in New York, and even a first offense can lead to license suspension, fines, and in some cases jail time.

If you or someone you know is facing a DWI or DWAI charge in the region, The Inniss Firm, PLLC, based in nearby Middletown, New York, focuses on criminal defense cases tied to impaired driving. The firm is led by attorney Randall F. Inniss, a former New York State Trooper with more than two decades of law enforcement experience before he became a lawyer. That background gives him a distinct perspective on how these cases are built and defended. The Inniss Firm serves clients throughout Orange County and the broader Hudson Valley, including Washingtonville.

Final Thoughts