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In the past couple of years, especially since the pandemic, the historic Hudson Valley has become an increasingly popular destination in New York. After all, New Yorkers have long considered it a go-to weekend escape, and National Geographic even included exploring the region's antiques scene among its "coolest travel adventures" for 2024. While well-known destinations like Beacon and Hudson continue to be featured in travel blogs and magazines, the region's easy access from New York City has also helped bring attention to lesser-known communities across the valley. Among them is Middletown, in Orange County.
Located roughly 65 miles northwest of Manhattan, not far from the verdant peaks of the Shawangunk Mountains, this lively city of over 30,000 residents offers plenty of reasons to make a stop. Incorporated as a city in 1888, Middletown grew into a booming hub for the now-defunct New York, Ontario & Western Railway (O&W) and became a major manufacturing center. Today, the city has evolved into a haven for artists and creatives with several local arts and crafts organizations, including the Middletown Art Group and the Workshop Workshop. Much of its historic downtown is easy to explore on foot and is home to small boutiques, breweries, and local shops.
Nature is never too far away. The Middletown Reservoir Trails, about a 10-minute drive from downtown, offer more than 8 miles of hiking and biking routes through a protected watershed. The city also has a wide range of dining options, from classic New York diners to Italian pizzerias and fusion restaurants. That diversity is reflected in the community itself: Niche ranks Middletown among New York's more diverse places to live.
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Exploring downtown Middletown: Where to go and what to see
Walking is one of the best ways to explore downtown Middletown. Many of its historic Victorian and early 20th-century commercial buildings are clustered around North Street, Main Street, and nearby blocks. Several have benefited from restoration and improvement projects funded through New York State's Downtown Revitalization Initiative. A prime example of this successful urban renewal is the Rail Trail Commons. Constructed inside a former Woolworth building, it serves as an indoor-outdoor pedestrian corridor connecting the downtown directly to the 19.5-mile Orange County Heritage Trail. It stretches all the way to Harriman, a true wild haven cut through by the Appalachian Trail.
North Street is lined with independent businesses like Open Concept Retail, a boutique focused on fashion, wellness, and locally curated goods, and DAYES Coffee Roasters, which offers enzyme-fermented coffee. Throughout downtown, you'll also spot large murals painted by regional artists, including one by Alex Mills celebrating Middletown's history as a railroad hub.
Another cultural highlight is the Paramount Theatre on South Street. Originally opened in 1930, the Art Deco venue still hosts a rotation of movie screenings, including Golden Age Hollywood classics like "Casablanca" and "Roman Holiday," as well as more recent releases, live concerts, and stand-up comedy shows. Just a short 10-minute walk away, you can find the Webb Horton Mansion, designed by local architect Frank J. Lindsey and built between 1901 and 1907 at a reported cost of $1 million. By the mid-20th century, the local community helped secure the estate — now known as Morrison Hall — for the creation of Orange County Community College, now SUNY Orange.
Eating your way through Middletown's bustling food scene
Middletown also has a varied food scene. This isn't surprising; New York is home to some of America's best eats after all. Piccolo Cucina e Vino is one of the city's best-known Italian restaurants, boasting a 4.7-star rating on Google. The name Piccolo — meaning "small" in Italian and inspired by the owner's family name — reflects the restaurant's intimate approach to dining. Menu highlights include fresh cavatelli with tomato, mushroom, and spinach, topped with Parmesan, as well as a wide selection of pizzas and paninis. Another standout destination for Italian food lovers is Pizza e Birra. Here, you can sample everything from shareable bites like fried calamari and crispy mozzarella balls to juicy burgers and signature pizza sandwiches, all paired with a selection of beers.
To switch things up, head to Dos Amigos Restaurante Mexicano on Bloomingburg Road. Among the must-tries are the signature Fajitas, stuffed with meat and shrimp, and the steak a La Mexicana. If you are in the mood for Caribbean cuisine, Yaadstyle Restaurant has you covered with its signature jerk chicken, shrimp curry, and steamed fish. For classic American diner fare, Kaz Americana offers breakfast staples such as pancakes with syrup and butter and omelets filled with feta, peppers, and onions.
The city is also a convenient base for exploring other beautiful small towns across New York. It's just a 90-minute drive from the Big Apple, with the nearest airport, New York Stewart International Airport (SWF), just about 20 miles away. For international arrivals, New York City's John F. Kennedy International Airport (JFK), LaGuardia Airport (LGA), and Newark Liberty International Airport (EWR) are also all within a 1.5-hour drive. For an overnight stay, consider Residence Inn by Marriott on Tower Drive or the Candlewood Suites by IHG, both of which are top-rated stays.
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Read the original article on Islands.
