This past weekend we visited Pleasant Valley, New York, a small hamlet northeast of Poughkeepsie along Route 44.

I discovered that Pleasant Valley was first settled in 1762 as part of the Crum Elbow Precinct of the Great Nine Partners Patent — land the Wappinger Native Americans once inhabited before it was “purchased” by early colonists. The area was originally called Charlotte. In 1786, Charlotte was divided into Clinton and Washington Precincts, and in 1821, the town of Clinton split again into Clinton, Hyde Park, and Pleasant Valley.

Settlers were drawn by Wappingers Creek, whose steady water power fueled farming and milling. Today, Pleasant Valley’s historic Main Street and its proximity to the Franklin D. Roosevelt and Eleanor Roosevelt homes make it a charming Hudson Valley stop.

Pleasant Valley, NY

Mill Site Museum & Memorial Park

The Mill Site Memorial Park sits on the site of the original “Lott’s Mill,” which may have existed as early as 1739 or 1757, though it was most likely built around 1763. Over the years, numerous owners ran it as either a grist mill (grinding grain) or a textile mill (processing wool or cotton).

By 1795, the mill was a major operation: three stories high, 75 feet long, and 30 feet wide, with 110 acres, a dwelling house, potash works, and a 44-by-24-foot store selling dry goods and groceries.

The mill burned down in 1815 while operating as the Pleasant Valley Manufacturing Company, impacting more than 50 local families. It was auctioned off for $13,100 (about $298,000 in today’s money) to John De La Vergne and Luther Thwing, who rebuilt it as a cotton mill in 1816.

Thomas Garner & Co. later operated the mill for 53 years, employing nearly 80 workers—some as young as eight. Between 1913 and 1984, three more companies used the mill for dyeing fabric or making buckram, a stiffened cloth used for bookbinding, hat making, clothing, and draperies.

After briefly serving as a shopping center, the mill was destroyed again by a suspicious fire in 1994. The office building was restored in 2002, and the site became Mill Site Memorial Park around 2004. Half of the original property is now home to a McDonald’s. (But don’t park there, they don’t like that.)

Today, the park is a peaceful spot for a walk among the ruins. When the Mill Store House is open, visitors can explore exhibits inside. The Mill Site Museum is open by appointment. Check the town calendar for special open houses usually held around Halloween, Christmas, Chanukah, Purple Heart Day, Pleasant Valley Day, and an annual Memorial Day ceremony.

The Village Diner and Pancake Factory

Before our mill visit, we had brunch just a few minutes away at The Village Diner and Pancake Factory—famous for decadent pancakes and French toast platters. The drink menu has some fun surprises, including the “Caramelo,” a caramel latte for only $5. Come hungry. Really hungry.

I really enjoyed our afternoon in Pleasant Valley.

There’s something about walking through a place where so many generations have worked, lived, and rebuilt that makes you slow down and imagine what life was like back then. The Mill Site Memorial Park blends that history with a quiet, peaceful spot to wander, and I love that the restored Mill Store House keeps the story alive. Pair that with a stop at the Village Diner for pancakes and a caramel latte, and you’ve got the perfect mix of local flavor and small-town charm.

‘til next week, happy exploring!
Kathleen

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