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Just five square miles in size, the hamlet of Highland is situated on the cliffs that rise above the Hudson directly opposite the city of Poughkeepsie. The area was settled in 1754 by Anthony Yelverton, an early entrepreneur who built a sawmill and a brickyard there, as well as his home, which today is Ulster County’s oldest wooden structure and is listed on the National Register of Historic Places. 

In the 1820s, farmer Philip Elting began what was derisively called “Philip’s Folly,” erecting buildings at a point along the north-south route from Newburgh to Kingston, where the hamlet now stands. In 1845, the town of Lloyd (of which Highland is the main part) was formally established. Subsequently, the village became something of a railroad hub with the 1889 opening of the (at the time) world-famous Poughkeepsie Railroad Bridge and the laying of a trolley line, which ferried tourists to the summer resorts in the western part of the county.

Today, Highland (pronounced “high land” not “highlind”) is home to about 5,600 residents. The hamlet is renowned for the wide variety of outdoor activities available within its borders and nearby. The area has no fewer than six parks — such as Berean Park at the Reservoir, which includes, according to resident Mary Phillips, “the best kept secret in Highland”: a beach and swimming in the summer. Located just off busy Route 299, Chodikee Lake is a prime spot for fishing, canoeing, and kayaking. Six of the 14 vineyards on the Shawangunk Wine Trail, as well as a variety of pick-your-own farms — apples, pumpkins — are a stone’s throw away.

But it’s the easy access to two important hiking/biking trails that has this area buzzing. Since its unveiling in 2009, upwards of 700,000 visitors each year have trekked across the revamped railroad bridge, which is better known today as the Walkway Over the Hudson State Historic Park. Many of those visitors also used the Hudson Valley Rail Trail, a 2.5-mile paved route that was extended an additional 1.2 miles to connect with the Walkway in 2010. “Traffic has just exploded because of the Walkway,” says Phillips, 74.  

Phillips’ observations are confirmed by Highland resident Charles Glasner, chairman of the Town of Lloyd Economic Development Committee, who cites Mountainside Woods (a long-term housing project at the base of Illinois Mountain) and Hudson Valley Wine Village (a multimillion-dollar development set to include a hotel, convention center, restaurant, and more than 800 houses) as evidence that more out-of-towners are finding the Highland/Lloyd area an attractive place to live. “They want the quality of life that Highland has worked to maintain,” he says. “We have all these parks, and, with our proximity to Metro-North in Poughkeepsie, we’re close to New York — but not too close.”

rocking horse ranch horseback riding rocking horse ranch kids

Highland’s Rocking Horse Ranch offers fun for the entire family

The influx of both visitors and new residents has no doubt fueled the local economy. Three B&Bs — as well as the Rocking Horse Ranch Resort, a fixture in the region since 1958 — offer lodging, and with “busloads of people coming in from out of the area to use the Walkway,” says Glasner, “they are really busy.” Recently opened restaurants include Walkway Café and Catering, Asian Garden (we hear the sushi is top-notch), and Vigneto Café (with pasta made on the premises), while old standbys the Would, Mariners on the Hudson, and Coppola’s La Fantasia are still going strong. Il Mercato Italian Marketplace, a wholesaler that also welcomes retail customers, opened last December, offering everything from artichokes to ziti at affordable prices; the Hudson Valley Sausage Company, owned by a Highland native, is also new on the scene. Glasner says projects on the horizon include a new brewery, as well as the creation of a rezoned “Gateway District” on Route 9W, which would allow some properties to include both housing and commercial units. 

Quite a lot of activity for such a small area — but the character of the town is little changed. “People still smile at you in the supermarket,” says Phillips. “There’s a small-town friendliness here; it’s a microcosm of America.” 

Chatting with Mary Phillips, a 17-year resident of Highland

Q: What do you like most about your town?
A: It’s the world’s most convenient place to live. You don’t have to travel too far to get to a supermarket, or to a hiking trail. I like that I have the opportunity to take part in outdoor activities right from my front door.

Q: How has the area changed since you moved there?
A: The Walkway brought more people and more cars; the population has definitely increased since I came. But I love the Walkway — I’m an ambassador for it. We saved a treasure from destruction.


Related: Walkway Over the Hudson Opens
What to do: Upcoming events in Highland
Read more: All stories about Highland, NY


 

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