Montgomery Is a Hub for History and the Arts in Orange County

With charming shops and eateries in town and family-friendly events throughout the year, Montgomery is a delightful place to call home.

Back in the 1700s—before Montgomery was formally incorporated in 1810—the area’s fertile land and access to water lured farmers to settle along the Wallkill River. As more people moved to the village, industry grew with the establishment of a grist mill and eventually Montgomery Worsted Mills, a textile factory.

Much of that original community still exists, particularly in the Bridge Street and Union Street–Academy Hill districts. Several pre-Civil War era buildings are home to shops and residents—and Montgomery is dedicated to historic preservation.

While the town still has ample farmland, its picturesque village and close-knit community are the main draws for newcomers. Montgomery, along with Maybrook and Walden, is one of three villages that make up the larger Town of Montgomery. It’s home to nearly 3,800 people, including Heatherlyn Nelson, owner of Union Street’s Inglenook Marketplace.

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She moved here in 2016 from Brooklyn, attracted to the village’s central location and easy access to hiking, shopping, and Stewart Airport. Nelson likens the town to Stars Hollow from the TV series “Gilmore Girls:” “It’s a cozy little village, not too big, and everyone has local pride. It’s a vibe, especially in the fall.” Randi Picarello, village trustee and executive director of the Greater Business Council of Montgomery (GBCM), agrees. “We have a lot to offer; it’s a great place to work, play, and stay.”

Historic buildings on Union Avenue.
Historic houses along Union Avenue. Daniel Case, CC BY-SA 3.0, via Wikimedia Commons

The Culture

Throughout the year, Montgomery is bustling with events. The Wallkill River Center for the Arts has open gallery hours every weekend and hosts a variety of classes for adults and kids, from jewelry making to oil painting. ARTBOX Studio displays the work of local artist Rebecca Cornell, and hosts paint and sips and children’s classes.

In the summer, locals head to the Clinton Street bandstand on Thursday nights for free concerts. City Winery Hudson Valley, housed in the former Montgomery Mills, also regularly hosts multi-genre concerts at their riverfront property, along with comedy sets, murder mysteries, wine and food events, and more.

Family Life

Children attend schools in the Valley Central School District. There are currently 4,103 students across four elementary schools, one middle school, and one high school; the district has a B+ overall rating on

Montgomery hosts many family-friendly events, including March’s St. Pat’s Ramble 5K and Parade, a Memorial Day Parade, and General Montgomery Day in September. Next month, their Old Fashioned Holiday Weekend on December 9 will feature a vendor fair, a tree lighting ceremony, and an appearance from Santa.

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The Wallkill River flows around the edge of town.
The Wallkill River flows around the edge of town. Courtesy of City Winery Hudson Valley.

On the Town

Stroll through the village to find a variety of shops like Inglenook Marketplace, a home goods store, the Montgomery Antique Center, Montgomery Mercantile, and Astoria Hudson, which carries women’s clothing and accessories. The village is also home to several specialty beauty spots like Blo and Glo, OMGbrows, and Coven Salon and Spa.

There are a range of dining options including the Iron Café for all-day breakfast and lunch, City Winery Hudson Valley for elevated American fare, RoseMary’s Pub & Grub, The Borland Inn & Brunch House, Copperfield’s Pub, and 88 Charles St. Restaurant for Italian food.

Even if you don’t live in Montgomery, the area is a great place to visit for the weekend. “You can hike, camp, kayak, pick apples, all these really cool things,” says Picarello. Veterans Memorial Park is home to pickleball, basketball, and tennis courts, as well as a baseball field and a dog park. The Wallkill River runs alongside the edge of the village; canoes and kayaks can be launched around City Winery and the Veterans Memorial Park. You can also go boating in the pond at Winding Hills Park (and ice fishing in the winter, weather permitting).

Nelson has found a tight community in Montgomery and says that newcomers are welcomed with open arms. “People here want the village to be cute, clean, safe, and welcoming. As long as you abide by those rules, you’re good to go.”

To find a real estate agent in Montgomery or any Hudson Valley town check out

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Related: Pawling Is a Small Town With Charm in Southern Dutchess County

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