How to plan a slow weekend in New York State’s Orange County

Just 50 miles north of New York City, Orange County offers small-town Hudson Valley charm, where rolling hills and Appalachian peaks give way to winding rivers and glistening lakes. Across the county, you’ll find local artisans and boutique shops, alongside farm-to-table dining and a range of weekend stays — from historic manor houses to small bed and breakfasts. Together, they offer a quieter alternative to long-established New York State escapes like the Hamptons. Here’s a weekend guide shaped by the people and places that define the region.

Day 1: Artistic adventures upstate

Morning: To begin your weekend break, rent a car in New York City and head north to Orange County. For breakfast, stop at Mr Boba, a neighbourhood bakery in New Windsor known for its milk tea and cheesecakes, before continuing to Storm King Art Center, just five-minutes away. Set aside a few hours to explore the 500-acre outdoor museum, where trails wind through large-scale sculptures and installations — and mornings are typically the quietest time to visit.

Afternoon: Take time to explore Orange County’s independent shops and small creative communities. From Storm King Art Center, it’s around a 25-minute drive to Sugar Loaf Arts Village in Chester, where an eclectic mix of studios and stores showcases local artisans alongside a wide selection of antiques and collectables. Nearby, pause for a locally brewed beer at Tin Barn Brewing, which regularly hosts live music and events.

Evening: From Chester, continue driving around 25 minutes south to Warwick to check into Peach Grove House, a historic bed and breakfast dating back to 1850, known for its period architectural details and elegant guest rooms. The property also hosts seasonal events, including farm-led dinners with local chefs and occasional wellness retreats. After settling in, head to Pennings Farm Market, just a 10-minute drive away, where locally sourced dishes — such as Griggstown turkey burgers and roasted roots with ricotta — are served in a barn-style dining room.

Day 2: Escape to nature

Morning: Once you have checked out, head for breakfast at Blooming Hill Farm, around a 30-minute drive from Warwick. The Balthazar Bakery section of the menu includes freshly baked goods such as cheddar-chive scones and almond croissants. From here, continue northeast for a relaxed kayak or canoe trip. The Hudson River Greenway Water Trail is well suited to beginners and features multiple access points across Orange County. One of the most convenient is the Cornwall-on-Hudson Boat Launch, which has a small beach and easy access for kayaks. Stretching 256 miles toward the Adirondacks, the route lets you set the pace, whether you opt for a short paddle or a longer, more challenging journey.

Afternoon: After your paddle, fuel up at Dottie Audrey’s Bakery Kitchen in Tuxedo Park, around a 35-minute drive from Cornwall-on-Hudson. The menu focuses on homemade comfort food, with sausage and gravy baguettes, chilli mac and cheese and turkey toasties among the highlights. From here, it’s a five-minute drive to Harriman State Park, a 46,000-acre landscape of forested trails and lakes, popular for cycling, swimming and leisurely hikes. Aim to arrive in the late afternoon, when elevated viewpoints across the park offer expansive lookouts as the sun begins to set.

Evening: Make your way to Middletown, a 35-minute drive from Harriman State Park. Settle in for dinner at Saffron, a long-standing local favourite serving regional Indian dishes. While farms and orchards shape much of Orange County’s culinary identity, the diversity of towns such as Middletown and Newburgh has contributed to a varied dining scene, spanning Spanish, South American and Asian-influenced menus. Other restaurants to consider include House of Birria and Fuji Japanese Steakhouse. For the night, stay nearby at the Orange Inn Boutique Hotel, a historic property featuring modern interiors, around a 15-minute drive from central Middletown.

Day 3: Sample farm-fresh cuisine

Morning: Enjoy brunch at The Sugarhouse, the on-site cafe at the family-owned Finding Home Farms. Organic, home-produced maple syrup features prominently on the menu, pairing excellently with the buttermilk pancakes and sugarhouse waffles. Afterwards, spend time exploring one of Orange County’s farmers’ markets (open from May-onwards). There are several to choose from throughout the region, with well-established markets in Warwick (open 9am to 3pm) and Goshen (open 9am to 2pm), both within a 20- to 30-minute drive of Middletown.

Afternoon: The afternoon lends itself to exploring the region’s agricultural landscape, starting with a visit to Soons Orchards in New Hampton, one of many pick-your-own farms across Orange County. Produce varies by season: peaches and blueberries are typically ready for picking in summer, while pumpkins and apples take over in the autumn. From here, it’s a five-minute drive to Orange County Distillery at Brown Barn Farms, where you can sample local hops and cocktails and enjoy a late lunch from the on-site Melt Food Truck, serving grilled cheeses and cheeseburger sliders.

Evening: Continue your tasting tour with a visit to Warwick Valley Winery & Distillery  — a 15-minute drive from Orange County Brewing Company — where homegrown fruit is used to produce cider, spirits and a range of wines. From here, toast to a weekend well spent at Grappa Ristorante, an Italian-themed spot serving fresh pasta, meat and fish dishes, paired with pours from their extensive wine list or carefully crafted martini menu.