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Montgomery NY Area Information

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Almost exactly half way between Albany and New York City, Montgomery, NY is located in the northern center of Orange County. It was known many years ago as the hub of transportation for the area. Today, it still is, close to the New York State Thruway (Hwy. 87), the rail-hub at Montgomery Village HallMiddletown, and Stewart International Airport, which services JetBlue, Delta and US Airways Express. With its 2.5 mile long landing strip, Stewart was designated as an available emergency landing strip for the Space Shuttle.

Montgomery is also close to many of Orange County’s attractions, possibly foremost being the United States Military Academy at West Point. The USMA has been training our army’s officers since the Revolutionary War. Today, visitors can take tours of the academy, attend sports events and visit its many historic places.

Within easy driving distance down winding country lanes, you’ll encounter close by an endless variety of recreational opportunities. One favorite is the magnificent Minnewaska State Park Preserve. Enjoy hiking, bird-watching, swimming, snowshoeing, and horseback riding among its spectacular cliffs, sky lakes and waterfalls. Another place to enjoy the great outdoors is the Mohonk Preserve in the majestic Shawangunk Mountains. The Visitor Center is open daily 9am-5pm and the land from sunrise to sunset. The Shawangunks, or “Gunks” as the residents call them, are well known to rock climbing enthusiasts.

Goosepond Mountain, Bear Mountain and Harriman are a bit further away, offering hiking, camping, fishing, swimming, boating and many more activities. Bear Mountain actually has more visitors per year than Yellowstone National Park. Montgomery is also on the Wallkill river, a haven for brown trout, as well as the fly fishermen who seek them out.


Wineries are plentiful in the area, and make excellent day trips. If a hearty red or perky white wine is what you fancy, the award-winning Whitecliff Vineyard is just 10 minutes away featuring world class wines to sample in their rustic Tasting Room. The Brotherhood Winery, America’s oldest operating winery is one of sixteen vintners in the area. Escorted tours of these sites are a delightful way to see the winemaking process and and sample the local fare. If you’re looking for something a little stronger, visit Tuthills, the local distillery, for small-batch, handmade bourbons, ryes and whiskeys – New York’s first whiskey distillery since Prohibition.

Antique shops also abound in Montgomery and the surrounding area, with little shops popping up along winding nearby roads. The village also has a wealth of unique retail stores and cozy restaurants. One of the best places to eat according to locals as well as is The Cauldron, an Italian restaurant with outstanding food. They make their own pasta daily, and are always finding new twists on old favorites, such as their apple cider sangria. Another favorite is the Back Yard Bistro, which is literally in a back yard. It serves local fare with unusual pairings. Get a reservation because it only has seven tables.

For the serious shopper, nowhere is more perfect than Orange County’s famous
Woodbury Commons Premium Outlet. With 220 stores and restaurants, it is the largest designer shopping outlet in the nation.

An unusual attraction that has become popular around Orange County is hot air ballooning. Several companies offer flights for visitors wishing to get a bird’s eye view of the countryside from high above. Flights last three to four hours and usually come with lunch and wine. For those interested in getting to the ground a little faster, they can skydive The Ranch in Gardiner, just 15 minutes away, a year-round skydiving club and school offering state-of-the-art aircraft and instruction. Jump from 13,500 feet above the earth in tandem, freefall or simple solo flights.

And of course, when you’re in Montgomery, all around you are wonderful farms and farm markets dotted around the countryside. Buy farm fresh produce, cider, eggs and homemade baked goods. Sample the fudge or buy home made jams and preserves. Some farms have petting zoos, and there are always great activities for children. Four near Montgomery are the Manza Family Farm, which sells trees, shrubs and flowers, Wrights’ Farm Market, an apple orchard, the eighty year old Tantillo’s Farm Market, and Brookside Farm, which sells free-range beef, chickens, eggs and pork products. Enjoy year round riding and lessons at Willow Hill Farm with its spacious indoor and outdoor arenas.

The village of Montgomery holds a significant spot in New York’s Revolutionary War history. Nearby Fort Montgomery was the site of a major engagement in the war, and an interpretive center has been created there, offering a glimpse into early American history. The town is filled with many historic homes, churches and buildings, preserved through a vigorous local directive and the National Register of Historic places to maintain their authenticity.

The area is full of history. Historic New Paltz, 20 minutes away, has one of the oldest streets in America complete with original stone houses and an Old French Church. History is everywhere, and you will encounter historic plaques, sites and buildings wherever you go.

Also historically significant was Montgomery’s pre-history. In 1801 a prehistoric Mastodon skeleton was discovered on the farm of Captain Joseph Barber. The bones wereWooly Mammoth found in a strata of chalky soil known as marl which farmers often mined to apply to the farm fields. (Marl added aeration to the soil, and allowed crop roots to grow deeper.) During the time Mastodons (or Wooly Mammoths) roamed Orange County, the marl was a sticky, thick muck which the large mammals would become mired in. The animals became extinct at the last ice age, about 11,000 years ago.

More information can be found about Montgomery and its surroundings at the Village of Montgomery‘s website.

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