One Week in New York State: The Ultimate Itinerary

Day One: The Hamptons

After landing at either John F. Kennedy International Airport or La Guardia International Airport, you’ll already be in Long Island. From there, you can catch a Long Island Railroad train or get a taxi, Uber, or Lyft to the Hamptons town of your choice. Or you can rent a car, which might be the best option if you’re doing this whole itinerary since you’ll be covering a lot of ground and using public transit the whole time would be fairly complicated and time consuming.

There are a number of towns to choose from in the Hamptons, and they are all charming and beach-adjacent. The town you end up staying in may be dictated by accommodation availability and cost, but Bridgehampton, East Hampton, Water Mill, Sag Harbor, Sagaponack, Amagansett, or Montauk are all great options. Once you drop off your bags, use your first day to experience the area’s famous beaches. Just make sure you have a parking permit if you drive to the beach. If not, rent bikes or take a taxi. Some hotels offer beach shuttles.

After you’ve had your fill of the beach, get lunch at Lobster Roll, known for yes, its lobster roll, and other seafood dishes, since 1965. Save room for a slice of strawberry rhubarb pie or a milk shake.

Next, head to the Parrish Art Museum for a dose of modern art, and stop at Milk Pail market, which has pick-your-own apples and pumpkins in early fall. Otherwise, you can buy various fresh produce and flowers, depending on the season.

For dinner, make a reservation at Highway Restaurant, for Italian-accented farm-to-table American food. If you’re not too tired, check out the concert schedule at the Surf Lodge in Montauk.

Day Two: Day Trip to the North Fork

If you can tear yourself away from the beach, Long Island’s North Fork is worth exploring. Before you head out, get breakfast at Grindstone Coffee and Donuts in Sag Harbor, Goldberg’s Bagels in East Hampton, or Babette’s, also in East Hampton. You can either catch the ferry to Shelter Island and then the ferry from Shelter Island to Greenport (each ride is about 10 minutes), or you can drive back to Riverhead and up to the North Fork. Once there, spend the morning wandering around charming Greenport, popping into shops like design and vintage store Ray, jewelry shop Orenda, and garden and home store Clark’s Garden. Recharge with a cup of in-house roasted coffee at Aldo’s before having a seafood-centric lunch at Claudio’s.

After lunch, if it’s summer, head to Lavender By the Bay, a picturesque lavender farm that will make you think you’re in Provence—and have your camera ready. Then begin your afternoon of wine sipping, with stops at some of the island’s best wineries, like Macari Vineyards, Pindar Vineyards, and Sparkling Pointe.

Before sunset, head back to the South Fork, to Montauk, for a picture-perfect waterfront sunset at Navy Beach. Have dinner there, or post-sunset go to Marram or Sel Rrose.

Day Three: Beacon and Hudson Valley

Grab breakfast at Hampton Coffee Company and before leaving the Hamptons, stop at Levain Bakery for some of their famous cookies to go, so you have snacks for the road. To get to Beacon, it’s about a four-hour drive, or to take the train, you’ll need to take the LIRR to Penn Station and then get on the subway or a taxi to Grand Central to catch the Metro North to Beacon, and with needing all of the schedules to match up, it could take well over six hours.

Once there, you’ll probably be hungry, so get lunch at Max’s on Main or Beacon Pantry. Check in to your accommodation for the night and then make your way to the Dia: Beacon, an incredible modern art museum in an old Nabisco factory by the water. After, stroll along the waterfront and admire the mighty Hudson River.

In the evening, catch an independent film at the restored retro Beacon Theater, now called Story Screen Beacon Theater. After, have a drink at the attached vintage-themed Wonder Bar and then have a late Middle Eastern dinner at Ziatun or splurge on the farm-to-table cuisine at the Roundhouse Restaurant.

Day Four: Hudson Valley and the Catskills

Fuel up at Beacon Falls Café and if it’s Sunday, check out the Beacon Farmers Market for farm-fresh produce and baked goods. If you’ve got a sweet tooth, get some treats from Glazed Over Donuts.

If you’re a hiker, you’ll enjoy the hike up Mount Beacon, which is fairly steep but offers stunning views of the Hudson River and surrounding valley. It only takes about an hour-and-a-half and it well worth it. When you come down, hop in the car or a taxi over the Newburgh-Beacon Bridge to the other side of the Hudson River and head up to Woodstock. Woodstock is a funky town that makes an ideal base camp for exploring the surrounding Catskills region. Although there is a definite artist and hippie vibe, these days it also has several upscale spots along Tinker Street (the town’s main drag).

Have lunch at Dixon Roadside, Oriole 9, or Tinker Taco Lab, and wander into boutique shops like Three Turtle Doves, Candlestock, Shop Little House, and the Golden Notebook. Pop into Fruition for a craft chocolate pick-me-up.

If you’re up for it, drive about 30 minutes north to Kaaterskill Falls to see some of the natural landscapes that make the Catskills so special. Or drive about 20 minutes east to the charming town of Saugerties where you can try funky ice cream flavors at one of the smallest shops, appropriately called Alleyway Ice Cream, and relax a bit on Saugerties Village Beach on the Hudson.

For dinner, eat Italian food at Cucina or farm-to-table fare at Silvia, both back in Woodstock. After, visit Levon Helms Studio, a barn venue that was the home and recording studio of the famous drummer that has hosted performances by Elvis Costello, Phil Lesh, Dr. John, and Emmylou Harris.

Day Five: Ithaca and the Finger Lakes

In the morning, drive one town over to Phoenicia, to eat at the celebrated Phoenicia Diner, known for its delicious farm-fresh comfort food. From there, it’s about a three-hour drive to Ithaca, at the base of Cayuga Lake, one of the 11 Finger Lakes. On your drive, enjoy the stunning scenery, farmland, and small country towns you’ll pass.

Once in Ithaca, check in to your accommodation and then grab an excellent hamburger from Ithaca Ale House. The Finger Lakes are known as one of New York State’s best wine regions and Cayuga Lake has its own wine trail, with 14 beautiful wineries to try along the lakeshore. Also along the way is the Seneca Falls State Park where you can visit the historic Women’s Rights National Historic Park, where the first women’s rights convention was held in 1848. If you need a little nibble, hit up the Muranda Cheese Company.

You can also book a Cayuga Lake boat tour with Discover Cayuga Lake if you’d rather be on the water than alongside it.

Back in Ithaca, have pre-dinner craft cocktails at Bar Argos and then have dinner at the world-famous Moosewood Restaurant, known for revolutionizing vegetarian food. If you want to get a taste of the college scene (Ithaca is home to Cornell University), Chanticleer is a solid dive bar with pool tables and jukebox.

Day Six: Finger Lakes and Rochester

Start your morning at the Ithaca Farmers Market overlooking the lake, which has everything from a breakfast sandwich made from waffles to Sri Lankan food, plus things like bread, cider, and produce to buy for later. From the market you can walk along the Waterfront Trail, either to Stewart Park or Cass Park for great lakefront views.

Then, head over to Seneca Lake and Watkins Glen State Park to hike around incredible waterfalls and canyons. From there, follow the Seneca Lake Wine Trail if you want more samples of the area’s bounty, and stroll through the charming town of Geneva. Have lunch there, at FLX Fry Bird, and if you’re brave, try your hand at kitesurfing or windsurfing if the weather is right, or enjoy a sail with Sail Seneca.

Drive about an hour west to Rochester and have dinner at Lento, a farm-to-table spot that is one of the city’s best restaurants, or grab a tasty pizza at Tony D’s.

Day Seven: Buffalo and Niagara Falls

On your last day, drive about an hour and a half west to Niagara Falls. First go to Goat Island inside Niagara Falls State Park and check out various observation points on the rim of the falls. Take the wooden staircases and paths that bring you to the bottom of the smallest waterfall, Bridal Veil Falls, and be prepared to get wet! If you have time, book a ride on the Maid of the Mist boat for an up-close view of the mighty falls. 

For lunch, drop down to Buffalo and hit up the legendary Anchor Bar, the birthplace of Buffalo wings, or get a Beef on Weck, one of New York State’s finest food inventions, at Schwabl’s.

After lunch, head to the Darwin D. Martin House, one of Buffalo’s Frank Lloyd Wright prairie homes that are open for tours. Before dinner, stroll along Canalside, the city’s revitalized waterfront along the Erie Canal. Before heading to the Buffalo Niagara International Airport, have authentic Chinese food at Peking Quick One for dinner, or eat at Hutch’s, an upscale local favorite.