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Four Hudson Valley Towns Worth Crossing the Border For

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I have a confession to make. For the past few years, I’ve been having the travel equivalent of an extramarital affair with the Hudson Valley region of New York. I know, I live in Connecticut and write for its magazine; I should spend my free time with my beautiful state. But with Vermont-esque landscapes and equally Vermont-esque culture of transplanted New York City natives and hippies, the Hudson Valley are undeniably appealing. Here are the towns in the Hudson Valley I visit over and over. Don’t worry, Connecticut, I still love you … the Hudson Valley is just, well, different. 

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Downtown Cold Spring comes complete with river views.

Cold Spring

This riverside village is about as charming as it gets. Its Main Street slopes down toward the Hudson River, providing waterside views as you stroll along a classic strip dotted with antique shops, restaurants and cafes. For a drink, try Cold Spring Depot, a trackside bar and restaurant in a converted train depot with an outdoor beer garden in the heart of the village. Grab a cold treat at Moo Moo’s Creamery, which offers housemade, super-creamy, velvety ice cream, or take a hike at the popular Breakneck Ridge, an intense mountain hike that is almost a climb at times but rewards the brave with unbeatable views of the river valley. Theater fans cannot miss seeing a show put on by the Hudson Valley Shakespeare Festival, a talented theater company that performs on an outdoor stage with a panoramic view of the Hudson serving as a backdrop. Even the Bard himself would have trouble putting into words just how great the view is during these performances. 

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Hudson Highlands State Park Preserve, a mostly undeveloped preserve of nearly 6,000 acres, seen from Beacon.

Beacon

Just upriver from Cold Spring, Beacon is like its hipper, more organic, but slightly less refined and photogenic twin. Riding between the two communities via Route 9 is a scenic waterside drive well worth taking while you’re in the area. Once you’re in Beacon you’ll be treated to a Brooklyn-like assortment of shops, bakeries, restaurants and arts venues. My favorite spot for food is Ella’s Bellas, a gluten-free bakery so good that I make a point of going anytime I’m remotely nearby. (I generally avoid gluten-free options, consuming a daily diet roughly 93 percent gluten based.) The town is also home to the Hudson Valley Brewery, a critically acclaimed brewhouse that specializes in approachable sour beers and tropical IPAs. For a relaxing and flat riverside stroll, visit Long Dock Park. For something more intense, hike Mount Beacon. It’s a tough hike I’ve only completed once, but the views of the river valley are stunning.

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The 1.28-mile Walkway Over the Hudson between Poughkeepsie and Highland, New York.

Poughkeepsie

There is no better place to get a view of the Hudson River in all its glory than from the top of the Walkway Over the Hudson. Billed as the “world’s largest elevated pedestrian bridge,” it spans 1.28 miles over the mighty river via a historic railroad bridge converted in recent years to pedestrian use. The 21-story walkway provides a 360-degree view of the river below and land on either side. Whether you walk the whole span or just part of it, the views are amazing. After a visit here, I always head to Plan Bee Brewery, a farm brewery that specializes in sour and wild beers made exclusively with New York-grown ingredients. Other well-known landmarks include Vassar College and Locust Grove, a 200-acre estate designed in 1851 for the painter and inventor Samuel Morse with gardens, rare paintings, and views of the water. History fans will not want to leave the area without visiting the Franklin D. Roosevelt Presidential Library and Museum in nearby Hyde Park.

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Water Street Market is a European-inspired shopping village on New Paltz’s Main Street.

New Paltz

I normally stick to towns on the east side of the Hudson River, closer to Connecticut. But this wilderness enclave is worth crossing the water to visit. One of the most beautiful places I’ve been, the progressive town is framed by rolling fields and the white-chalk cliff face of the Shawangunk Ridge. Among the most popular climbing destinations in the country, the Shawangunk Ridge is home to several preserves. Though technically outside New Paltz, you won’t want to visit the town without spending some time in one of the preserves on the ridge. Minnewaska State Park Preserve is home to several crystalline lakes, with eye-catching ice blue water, and the freefalling Awosting Falls. In town you’ll find many destinations adorned with a rainbow flag and have a hard time eating anything that is not organic and vegan. One excellent spot is Bacchus, a brewpub, restaurant and billiards hall with great beer and a laid-back vibe.


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This article appeared in the July 2019 issue of Connecticut Magazine. You can subscribe here, or find the current issue on sale hereSign up for our newsletter to get the latest and greatest content from Connecticut Magazine delivered right to your inbox. Got a question or comment? Email editor@connecticutmag.com, or contact us on Facebook @connecticutmagazine or Twitter @connecticutmag.

The senior writer at Connecticut Magazine, Erik is the co-author of Penguin Random House’s “The Good Vices” and author of “Buzzed” and “Gillette Castle.” He is also an adjunct professor at WCSU’s MFA Program and Quinnipiac University