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New Paltz, Highland, Milton, Marlboro 

Country Roads

Walkway Over the Hudson and the Mid-Hudson Bridge.

David Morris Cunningham

Walkway Over the Hudson and the Mid-Hudson Bridge.

There are places whose character is easily identified and well defined. They have names that are synonymous with particular activities, attractions and lifestyles. But there are others that are less circumscribed, less predictable, and, in some ways, more interesting.  Such places give us the opportunity to discover hidden treasures and to be more creative in our perception of the world. The unassuming stretch of Route 299 east of New Paltz and Route 9W from Highland south, with its strip malls, fast-food restaurants, gas stations, and motels, wouldn't seem to offer much in the way of character or charm.  But to turn off the highway onto country roads is to be transported immediately into rolling hills and valleys full of apple orchards, charming historic towns, and stunning natural scenery. 

The Towns of Highland, Milton, and Marlboro may not be well-known destinations like some of their sisters in Ulster County, but they offer a variety of hidden gems all set in the natural splendor of the Hudson Valley.  And though we think we may think we know the Town of New Paltz, so defined by the presence of SUNY New Paltz, it, too, contains treasures that lie off the beaten path.

A Trail Runs Through It

Together with the Hudson River, one of the defining geological features that connects the towns is the Marlboro Mountains, a group of hogbacked mountains arranged in a 25-mile-long ridge extending from Newburgh to just south of Kingston.  They form a broken ridgeline running from the Ulster–Orange County border in the south to the mouth of Rondout Creek in the north. Considered to be part of the Ridge and Valley Appalachians, the mountains, which reach elevations over 1,100 feet, form an imposing geologic barrier just west of the Hudson River. Rising abruptly on their eastern flank, the Marlboro Mountains are known for their sweeping views of the region.

Just south of Route 299, about halfway between New Paltz and the junction of Routes 299 and 9W, is Tony Williams Park, where the Hudson Valley Rail Trail terminates on the western side of the Hudson River. The park lies at the base of Illinois Mountain, which is named after the state and is one of the highest peaks in the Marlboro range. During the early 1800s, there was a westward migration of New Englanders to the area of the former Northwest Territory, which included Illinois and Ohio. Some settlers, however, never reached their intended destination, being cut off by the swamps just west of the Marlboro Mountains. Setting up homesteads in the area, the settlers named local places and geographic features after the lands they never reached. Ohioville, near New Paltz, is an example of another area with the same etymological lineage.

The Rail Trail offers something for everyone, all year long. In fair weather, hike it or bike it, ride on horseback or roller blades, or take the little ones for a stroll. In winter, cross-country ski it or make your way on snowshoes. The Hudson Valley Rail Trail offers visitors a scenic tour through the former railbed that connected Ulster and Duchess Counties by train. Now, pedestrians and bikers can make the trip over the river via the spectacular Walkway Over the Hudson, the former Poughkeepsie-Highland Railroad Bridge and, presently, the eastern terminus of the Rail Trail. With plans for expansion in both directions, the HVRT and the Walkway have far exceeded planners' expectations for visitorship. The Walkway currently attracts over half a million visitors year, pumping  $24 million annually into the local economy.

Before or after your trip across the river, hop off the Walkway into the adjacent hamlet of Highland. Earlier in the 20th century, many Hudson Valley towns attracted families hoping to escape the heat and crowds of the city for the expanse of the countryside, and particular ethnic groups tended to cluster together. Highland attracted Italian-American families, and that heritage is still reflected in some of the shops you'll find, especially Elia's Market, a good old-fashioned Italian meat market with house-made sausage. Chef Mark Elia will even teach you the art of sausage making in his Old World Italian Sausage Making class! Elia also does catering and makes some of the best barbeque in the Hudson Valley.

For a quick bite, grab a slice at Three Guys Pizzeria on Vineyard Avenue or, for something different, get some dim sum at Asian Garden on Main Street.  For true Highlanders of the Scottish variety, stop in at Kiltmaker's Apprentice, where you can rent a kilt for that special occasion. Co-owner Doreen Browning can even fit you for a custom kilt made to order. A charming shop and well worth a visit—after all, when's the last time you shopped for a kilt? 

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  • Discovering Ulster County's gems often requires a trip off the beaten path.

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