New Windsor(United States) Travel 2026: Cheap Flights, Hotels & Top Attractions

For first-time visitors, the downtown New Windsor district is ideal, offering easy access to historic sites like the New Windsor Cantonment State Historic Site and scenic views of the Hudson River. Stay at The Windsor Hotel, a boutique property with elegant rooms and riverfront balconies, or opt for Riverbend Inn, a charming family-run bed & breakfast nestled in the Catskill Mountains. Both offer authentic local experiences, from farm-to-table breakfasts to guided nature walks through nearby trails.

Yes, Riverbend Inn stands out as an eco-conscious choice in New Windsor, featuring solar panels, rainwater harvesting systems, and organic gardens supplying its meals. The inn uses locally sourced materials in renovations and offers guests reusable water bottles and zero-waste amenities. It’s also part of the Green Lodging Network, ensuring sustainable operations. Located near the Catskill Forest Preserve, it promotes low-impact tourism with guided nature hikes and conservation talks.

Each autumn, New Windsor hosts the Catskill Arts Festival at Hudson River Park, showcasing regional painters, musicians, and performers in open-air concerts and exhibitions. Another highlight is the Colonial Living Day, organized by the New Windsor Historical Society, where visitors can experience 18th-century crafts, cooking, and dress-up activities. These events reflect the town’s deep-rooted heritage and vibrant creative community.

The Windsor Hotel offers the most breathtaking Hudson River views, with floor-to-ceiling windows in every room facing the river. Its rooftop terrace provides panoramic vistas, perfect for sunrise photography or evening stargazing. For a more secluded experience, Riverbend Inn features a hilltop deck overlooking the Catskill Mountains and river valley—ideal during fall foliage season when golden hues stretch across the landscape.

For couples, The Windsor Hotel offers a "Time Traveler's Romance" package including a private riverside dinner under fairy lights, a colonial-era themed dinner, and a stargazing session with a local astronomer. Alternatively, Riverbend Inn’s "Whispering Pines Suite" features a stone fireplace, handmade bath salts, and a secluded forest-view balcony—perfect for quiet moments amid the Catskills. Both options emphasize intimacy, history, and natural beauty.

Top trails near New Windsor include the Hudson River Trail, a 12-km path winding through oak forests and river cliffs, offering sweeping views of the Catskill peaks. The New Windsor Canyon Trail connects to the Catskill Forest Preserve, featuring waterfalls, clear streams, and seasonal color changes. Spring brings wildflowers, while fall paints the hills in fiery reds. Pack a map, hiking poles, and stop at designated rest points with picnic tables and overlooks for stunning photo ops.

Must-try dishes in New Windsor include Hudson River Perch Stew, a rich fish stew made with fresh-caught perch and wild herbs. Visit The Old Mill Kitchen for their signature Catskill Apple Pie, crafted with local Fuji apples and caramelized cream. Don’t miss the weekly New Windsor Farmers Market, where you can sample artisanal cheeses, raw honey, and organic produce straight from nearby farms—perfect for food lovers seeking authentic regional flavors.

Public transit in New Windsor is limited but functional. The New Windsor Bus Station connects to the Hudson Line Rail Service, linking to Albany and Binghamton. While downtown is walkable, rural areas require a car. The NY State Route 17 highway offers quick access to New York City (1.5 hours) and other regional hubs. For travelers exploring the Catskills or farmers markets, renting a vehicle is highly recommended due to infrequent bus schedules.

The best time to visit New Windsor is from April to October, when temperatures are mild and outdoor activities thrive. Spring brings blooming flowers and cherry blossoms, summer hosts music festivals and farmers' markets, and fall showcases the vibrant Catskill foliage—a prime time for photography. Winter offers snowy landscapes ideal for skiing and spa retreats, though some smaller lodges close. Avoid December holidays due to limited availability. September and October are optimal for scenery and comfort.

Photographers love Hudson River sunrise at The Windsor Hotel rooftop, where golden light reflects on calm waters. The Catskill Forest Trails in fall offer dramatic color gradients perfect for wide-angle shots. New Windsor Castle Ruins at golden hour provide striking contrast between aged stone and soft shadows. The Farmers Market offers vibrant colors and candid street scenes. Bring a tripod and wide-angle lens—ideal times: dawn and one hour before sunset.

Standout festivals include the Hudson River Music Festival in June, held at Hudson River Park, featuring folk and jazz acts with a fireworks finale. In September, the Catskill Harvest Fair celebrates agriculture with crop displays, pumpkin carving contests, and traditional turkey roasts. The Holiday Light Parade in December lights up downtown, with residents in vintage costumes marching through decorated streets—creating a nostalgic, festive atmosphere that draws visitors from across the region.