Begin at Bear Mountain State Park, just 45 minutes north of the George Washington Bridge. Walk the section of the Appalachian Trail that takes you through the Bear Mountain Zoo to see native Hudson valley wildlife, four trailside museums with exhibits on nature, geology and history. Picnic alongside Hessian Lake or grab a bite at the Bear Mountain Inn's Restaurant 1915 and Blue Roof Tapas Bar or the casual Hiker's Café & Stand 10.
After lunch, cross the Bear Mountain Bridge and turn left on Route 9D. Continue north for 7 miles to Boscobel House and Gardens in Garrison (closed on Tuesdays). Take a docent led tour of the mansion considered to be one of the finest examples of Federal-style architecture in New York. Stroll the gardens and grounds and take in the breathtaking Hudson River views.
Continue north 8.5 miles on Route 9D to see Dia Beacon's collection of contemporary art from the 1960's to present. The exhibition space, a converted industrial building sited on 31 acres on the banks of the Hudson River, is lighted only by natural sources.
A 5 minute walk from the museum will bring you to shops and restaurants in downtown Beacon or cross the Newburgh-Beacon Bridge to dine at one of many Newburgh Waterfront Restaurants. Depending on the day and season, you might be able to take a sunset cruise on the Pride of the Hudson or River Rose, before heading to your hotel. There are several hotels near the intersection of Routes 17K and 300 just 3 miles west of the Waterfront. Homewood Suites at Stewart International Airport is also close at exit 5A off Route 84.
Head south on Route 9W to the Quaker Street exit. A right turn will bring you into the charming village of Cornwall where Main Street offers a number of places to enjoy breakfast. Continue to Route 32 and follow the blue signs to Storm King Art Center just minutes from the intersection. This 500-acre outdoor park showcases contemporary sculpture with the scenic backdrop of the Hudson Highlands. Weekend workshops and entertainment are included with the price of admission. Make time to head west to travel on the Storm King Highway for spectacular photo moments.
Continue south of Route 9W to pay an afternoon visit to the United States Military Academy at West Point. One and 2-hour bus tours begin at the Visitor Center on Main Street in Highland Falls. Right behind the Visitor Center, explore the galleries at the West Point Museum which include art, weapons, and the history of the Corp of Cadets. Admission to the museum is free.
Spend the night at the historic Thayer Hotel on the West Point grounds or just enjoy a meal in the hotel's fine restaurant or a cocktail at their seasonal Zulu Time rooftop lounge overlooking the Hudson. Or, complete the loop and head back to the Bear Mountain Inn just 5 miles south for lodging. Before heading home, take a ride up to the top of Perkins Memorial Drive for amazing views of the Ramapo Mountains and the New York City skyline.