2-Week Best of New York State Itinerary

Visit New York City for its cultural, historical, and commercial attractions. Travel to upstate New York for the outdoors—forests, mountains, rivers, and lakes—as well as historic sites and picturesque villages. This 2-week New York itinerary will take you through the best of both.

New York City

view of Ellis Island surrounded by water with the New York City skyline in the distance
Pay a visit to Ellis Island, where you can look through historical photos and artifacts. Photo © felixmizioznikov/iStock.

Day 1

Start your day early with a visit to the Statue of Liberty and Ellis Island. Grab a slice of pizza or a simple lunch from a food truck to enjoy on The High Line and take in the latest art installations at a gallery or two in Chelsea and the Meatpacking District.

Browse in quirky boutiques or take a self-guided walking tour through Greenwich Village, SoHo, or other unique Lower Manhattan neighborhoods before having dinner at a popular local restaurant, such as upscale Eleven Madison Park or more affordable abc kitchen.

Cap off the evening with a cocktail at one of the city’s rooftop bars, such as the one at Hyatt Times Square, the tallest in the city, with views of both the Hudson and East Rivers.

Day 2

Spend the morning at the Museum of Modern Art before dipping into beautiful Central Park. From there, walk south on 5th Avenue, shopping or window-shopping along the way.

At night, brave the bustle of Times Square to take in a Broadway show and dinner in the Theater District. Visit the Empire State Building, open until 2am, to end the day with the lights of the city laid out before you.

Day 3

Start the day on the Upper West Side, paying a visit to the iconic blue whale at the American Museum of Natural History. Then, stock up on road-trip snacks at Zabar’s, or swap sides of the park to fill your art tank at the Guggenheim Museum or Frick Collection, both on the Upper East Side, before heading out of the city to explore other regions of the state.

The Hudson Valley

side entrance of the vanderbilt mansion in New York's Hyde Park
The Vanderbilt Mansion in Hyde Park. Photo © sphraner/iStock.

Day 4

Let the city recede in your rearview mirror and head north on Route 9 to Tarrytown. Though it’s just a 30-minute drive, you’ll notice a dramatic transition between the throbbing energy of the city and the more pastoral, rural rhythms of the Hudson Valley. Here, you can tour the historic homes of Washington Irving at Sunnyside, John D. Rockefeller Sr. at Kykuit, and Jay Gould at Lyndhurst.

If time permits, take a late afternoon walk through Rockefeller State Park Preserve. At night, dine in one of the area’s many excellent restaurants, such as the farm-to-table Blue Hill at Stone Barns. If your budget permits, overnight at one of the Hudson Valley’s castles; Castle Hotel and Spa, looming large over the Hudson River in Tarrytown, is one grand choice.

Day 5

Head north on Route 9 to Hyde Park, where The Culinary Institute of America offers a tasty lunch at one of its signature restaurants.

Nearby, you’ll also find FDR’s Home, Library, and Museum and lovely, free paths overlooking the Hudson within the Vanderbilt Mansion property. Farther north is Rhinebeck, a town featuring indie bookshops, cafés, an organic and sustainable product farmers market on Sundays, or the unique Aerodrome classic biplane show on summer weekends.

The Capital-Saratoga Region

Olana castle perched on top of a hill in the upper Hudson Valley
Olana State Historic Site was built in 1870 by landscape artist Frederic Church, with the help of architect Calvert Vaux. Photo © DeniseBush/iStock.

Day 6

Continue north another 40 miles or so to the historic town of Hudson, home to the Persian-style castle Olana, numerous antiques shops, and plenty of restaurants for lunch. Afterward, head on to Albany, about a half hour farther north on I-87. Stop at Albany Heritage Area Visitor Center for a good introduction to this historic region or go straight to the New York State Museum at Empire State Plaza, admiring impressive art and architecture en route. For a free, bird’s-eye view of Albany, take an elevator to the observation level of Corning Tower.

Day 7

Continue another 40 minutes north on I-87 to Saratoga Springs. In the morning, hit the track for breakfast and enjoy a behind-the-scenes tram tour, or drop some belongings to secure your seats or picnic table for afternoon races. Head downtown to shop and eat lunch along quaint Broadway, admiring the street’s historic buildings. If you’re not returning to the races, take in a spa treatment or go for a dip in one of the pools at Saratoga Spa State Park, or drive out to nearby Yaddo and stroll its calm, pretty gardens.

Day 8

Before leaving Saratoga, make a stop at Saratoga National Historical Park, where battles that turned the course of the American Revolution were fought. From there, continue on Route 9 another half hour to Glens Falls, home to the Hyde Collection, a mansion filled with Old Masters paintings. Alternately, head to the town of Cambridge and the nearby New Skete Monastery, famous for its onion-domed structures and pay-by-honor-system cheesecake made by New Skete nuns.

The Adirondacks

adirondack chair sitting on the shores of Lake Placid
Enjoy the scenery of Lake Placid. Photo © Dreamstime.

Day 9

Head back to Saratoga Springs and take I-87 north to Lake George. Along the way, stop at Grant Cottage to see the literal deathbed of the former U.S. president. Keep driving 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; if time permits, observe feats performed year-round at the Olympic Ski Jump Complex or go snowless sledding with a bobsled experience on the Olympic track. If your interests are more historic, visit the John Brown Farm State Historic Site.

Day 10

Drive eight miles south of Lake Placid and visit Adirondak Loj on the shores of Heart Lake. Set out from the lodge and spend the day hiking, snowshoeing, or cross-country skiing on Adirondack trails, depending on the season. If you have small children, head instead to nearby Tupper Lake, where The Wild Center, opened in 2015, will delight the whole family with its interactive nature exhibits.

Day 11

Start heading south again, taking leisurely, scenic Route 30 through the heart of the Adirondacks. You can stop at Adirondack Experience along the way, but budget 3-4 hours for driving; your destination is the Catskills. Overnight at The Graham & Co., a hip hotel in the town of Phoenicia.

The Catskills

rocky outcropping in mohonk preserve
Hike through the 5,600-acre Mohonk Preserve. Photo © fallbrook/iStock.

Day 12

Fuel up at one of Phoenicia’s breakfast spots and then head east toward Woodstock and Saugerties. Along the way, you may want to stop for a ride on the Catskill Mountain Railroad or take a short detour to Mount Tremper to see the Kaatskill Kaleidoscope. Woodstock and Saugerties are both home to numerous restaurants, shops, and B&Bs. In Saugerties, be sure to visit outdoor sculpture park Opus 40.

Day 13

From Woodstock and Saugerties, head south to explore the tiny canal town of High Falls. Along the way, take a break at one of the area’s many organic farms to pick your own snacks of apples or raspberries, natural fuel to get you ready for climbing the Shawangunks before you check in at Mohonk Mountain House and Preserve. The Victorian mountaintop castle is more than 140 years old and the region’s loveliest resort. Purchase a day pass to enjoy miles of gorgeous hiking trails, dotted with hand-hewn wooden gazebos for rest stops. If visiting in winter, take a cocoa break by the massive stone ice-skating pavilion’s bonfire.

Stay for the night 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 down the south side of the mountain past New Paltz and historic Huguenot Street to Bear Mountain State Park.

Day 14

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, to Washington’s Headquarters, Storm King Art Center, or West Point.

Then head back to New York City to finish the trip with a walk across the Brooklyn Bridge. Toast to the Empire State at one of the city’s craft cocktail bars.


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