An essential guide to exploring Orange County, New York

Stretching north along the Hudson River towards Albany, the Hudson Valley is characterised by rolling farmland, wide-open scenery and a strong creative culture. At its heart lies Orange County, a place defined as much by its natural setting as by its small towns and cultural landmarks. Just 50 miles from New York City, the region offers unhurried weekends for those looking to escape the hustle and bustle of the city. Whether you’re an active adventurer keen to hike the Appalachian Trail and paddle the Delaware River, or a culturally curious visitor drawn to the area’s galleries and exhibitions, there’s plenty to explore. Here’s an insider's guide to exploring this bucolic region.

What to do

Despite being home to the historic villages of Warwick and Montgomery and the vibrant cities of Middletown and Port Jervis, it's Orange County's sprawling countryside that draws most visitors. Take the famous Appalachian Trail, for example, which cuts through two of the county's state parks, Bear Mountain and Harriman State Park. The trail covers around 40 miles of rugged scenery, with highlights including panoramic views from the Cat Rocks overlook and the narrow boulder passage, also known as the Lemon Squeezer which requires hikers to squeeze through a tight granite gap.

For hiking enthusiasts, there are the challenging mountain trails of Schunnemunk and Storm King State Parks, while gentler options include the paved Heritage Trail and the forested pathways of Winding Hills County Park. Beyond walking routes, there are plenty of other adventurous activities on offer, including the roller coasters and climbing towers of Legoland, located in the town of Goshen, the county seat.

Cultural highlights include the sculptural gardens at Storm King Art Center and the United States Military Academy at West Point, with year-round guided tours of its historic grounds. Elsewhere, Sugar Loaf Arts and Crafts Village is a great place to soak in the county’s creative scene, with eclectic galleries and artisan workshops open to visitors. Seasonal events also take place throughout the year, most notably the New York Air Show, a midsummer spectacle of aerobatic displays and crowd-pleasing stunts.

Where to eat & drink

The region is known for its award-winning farm-to-table restaurants, craft breweries and distilleries. Angry Orchard Cider House, based in Walden, produces the top-selling cider brand in the US and is home to a popular cider bar where locals sip their favourite tipple. Craft beer fans can visit Middletown’s Equilibrium Brewery, known for its IPAs, and Newburgh Brewing Company, housed in a reclaimed 1850s building, serving locally sourced brews alongside tacos, burgers and quesadillas.

Dining highlights include Oak & Reed in Middletown, championing seasonal ingredients, alongside City Winery Hudson Valley, set in a restored 19th-century textile factory, known for its award-winning wines and chef-led pairing menus. Blooming Hill Farm is another favourite, taking a farm-to-fork approach. Beyond restaurants, visitors can explore pick-your-own farms and browse farmers’ markets, or time their trip to coincide with harvest celebrations. Among the standouts is Warwick Applefest, an autumn event with live music and crafts, drawing thousands of visitors each year.

Where to stay

Ranging from historic estates to family-owned guesthouses, independently run accommodation is a defining feature of the region. In Chester, Glenmere Mansion offers an elegant stay, with an on-site spa and four restaurants, while the Neversink River Resort in Godeffroy provides camping and RV options across a scenic 70-acre campground. In Warwick, the boutique Peach Grove House offers a more intimate alternative to the area’s larger hotels. Lastly, The Orange Inn is a boutique property in Goshen. Originally constructed in the 1800s, the heritage building is part of the Hudson Valley town’s historic fabric.