Start your day early with a visit to the Statue of Liberty and Ellis Island . Grab a slice or a simple lunch from a vendor’s cart to enjoy in the High Line Park  and take in the latest art installation. Browse through quirky boutiques and galleries or take a self-guided walking tour through Greenwich Village , SoHo , or other unique Lower Manhattan  neighborhoods before finishing the night off in one of the area’s top restaurants  or hot Chelsea clubs .
Spend the morning at the Museum of Modern Art , before dipping into beautiful Central Park . When the park ends at 59th Street, continue south on 5th Avenue , shopping or window-shopping along the way. At night, brave the Times Square  madness to take in a Broadway show and dinner in the Theater District . Visit the Empire State Building , open until 2 a.m., to end the day with the lights of the city laid out before you.
In the morning, hit the Upper West Side  to pay a visit to the iconic blue whale at the American Museum of Natural History , stock up on road trip goodies at Zabar’s , or swap sides of the park to fill your classic art tank at the Guggenheim Museum  or Frick Collection  on the Upper East Side . Check for free evening concerts at Manhattan School of Music , like Café Jazz featuring student jazz combos in an intimate setting or the school’s impressive 19-piece Afro-Cuban Jazz Orchestra.
Head north on Route 9 out of New York City for about 30 minutes to Tarrytown  in the Hudson Valley , where you can tour the historic homes of Washington Irving at Sunnyside , John D. Rockefeller, Sr. at Kykuit , and/or Jay Gould at Lyndhurst . If time permits, take a late afternoon stroll in the Rockefeller State Park Preserve . At night, dine in one of the town’s many excellent restaurants; if your budget permits, overnight in one of its two castles.
Head north on Route 9 to Hyde Park , where the Culinary Institute of America  offers a tasty lunch at its Apple Pie Bakery Café. In Hyde Park, you’ll find Franklin Delano Roosevelt’s Home, Library, and Museum  and the lovely free paths overlooking the Hudson within the Vanderbilt Mansion  property. Further north is the adorable town of Rhinebeck , which features indie bookshops, cafés, a lovely organic and sustainable product farmer’s market on Sundays or the unique Aerodrome classic biplane show  on summer Saturdays. Classic “drive-ins” show current movies in both Hyde Park  and Catskill , complete with dancing popcorn.
Continue north another 40 miles or so to the historic town of Hudson , home to a Persian-style castle, Olana , the American Museum of Firefighting , some 60 antique shops within five blocks, and plenty of restaurants for lunch. Afterward, head on to Albany , about a half hour further north on I-87. Stop at the Albany Heritage Area Visitor Center  for a good introduction to this historic region or go straight to the New York State Museum  at the Empire State Plaza , admiring impressive architecture en route.
Continue another 40 minutes north on I-87 to Saratoga Springs . In the morning, hit the Saratoga Race Course  for breakfast and enjoy a behind-the-scenes tram tour or drop some belongings to secure your seats or picnic table for the afternoon races. Stroll back to town to shop and eat lunch along quaint Broadway . In the afternoon, non-race fans can take in a spa treatment or go for a dip at the Saratoga Spa State Park  or enjoy a classic poolside cocktail as guests at the unique Adelphi Hotel .
Before leaving the Saratoga area, make a stop at the Saratoga National Historic Park , where the battles that turned the course of the American Revolution were fought. Then continue on Route 9 another half hour to Glens Falls , home to the Hyde Collection , a mansion filled with Old Masters paintings.
Take Route 9N north along the shores of Lake George  and Lake Champlain . In picturesque Westport , continue on Route 9N (which turns west), past the mountain villages of Elizabethtown  and Keene , to Route 73, which leads to Lake Placid. Spend the rest of the day exploring Lake Placid  and, if time permits, observe the feats performed year-round at the Olympic Ski Jump Complex , go snowless sledding with a bobsled experience on the Olympic track and/or bring the adrenaline down a notch at the John Brown Farm State Historic Site .
Drive eight miles south of Lake Placid and visit the Adirondak Loj  on the shores of Heart Lake. Set out from the lodge and spend the day hiking, snowshoeing, or cross-country skiing on trails in the Adirondacks .
Take Routes 73 and 9N east to the New York Throughway (I-87) and head south to the Albany  area, where you can pick up I-88, which leads to the Cooperstown  area. Have a late lunch in the pretty village and then explore its shops and lakefront or visit one of its three first-class museums: the National Baseball Hall of Fame , Farmers’ Museum , and Fenimore Art Museum . Have a cocktail at the Otesaga Hotel , a delicious grande dame of a 1902 hostelry.
Spend the morning exploring more of Cooperstown’s attractions. After lunch, take Route 28 south, which leads into the heart of the Catskills . Pass the pretty mountain towns of Andes and Margaretville before arriving in Woodstock  and Saugerties , both home to numerous restaurants, shops, and B&Bs. Woodstock’s Sunday afternoon drum circle will unleash your inner hippie in this notorious artist colony village.
From the Woodstock/Saugerties area, head south to explore the tiny canal town of High Falls , breaking in one of nearby Stone Ridge ’s organic farms to pick-your-own hiking snacks of apples or raspberries before climbing the Shawangunks ’ heights up to the 140-year-old Victorian mountaintop castle that is Mohonk Mountain House .
Pop for a day pass to enjoy the gorgeous 85 miles of hiking trails, dotted with hand-hewn wooden gazebos for rest stops, or to have a cocoa break by the massive stone ice skating pavilion’s bonfire. Stay on for the night at the inclusive resort and take time to enjoy afternoon tea and cookies, a wealth of unique activities, or the resort’s excellent spa. If more rustic accommodations are preferred, continue on down the south side of the mountain past New Paltz  and historic Huguenot Street  to Bear Mountain State Park.
Take Route 9W south to Bear Mountain State Park , where you can take a short hike or drive to the top of Bear Mountain where a clear day reveals the NYC skyline. Continue, depending on your interests, for a visit to Washington’s Headquarters , the Storm King Art Center , or West Point .