A Road Trip Guide to Upstate New York

And North curated guide to upstate New York featuring the best of travel and lifestyle north of New York City.

A highlight of any And North summer has always been escaping New York City to travel upstate with our friends and loved ones. It still amazes us how swiftly the cityscape turns to the countryside; we will never tire of the sweeping scenery, rolling hills and winding roads that await us each time. For us, this past summer has been everything we thirst for and more, complete with lakeside picnics, pond dips, drive-in movies, and long-lasting days spent visiting the many local farm stands, all varied and as wonderful as the scenic towns where they can be found.

There are a number of transportation options to get yourself upstate, but frankly, Upstate New York was made for driving and so renting a car is our preferred mode for the freedom it yields and its power to transform great adventures into unforgettable ones. Thanks to Sixt car rental, we had the fortune of bidding summer goodbye from the comfort of an affordable, high-end car while visiting some of our favorite upstate destinations. Our Cadillac CTS could not have been more of a treat to cruise around in with its plush seating, air conditioning and ample room for bags and anything else we felt like picking up along the way.

Sixt’s new Battery Park location turned out to be a great starting point for our weekend plans, which included an initial stop in Tarrytown to roam the grounds of Lyndhurst Estate, a farm-driven lunch at Stone Barns in nearby Pocantico Hills, and plenty of time to visit the shops of charming Cold Spring before making our way to Valhalla Highlands to settle into our historic Airbnb lodge on Lake Valhalla. As we coasted north on the Harlem River Drive and watched the skyline disappear from the rearview mirror, you could hear a collective sigh of satisfaction stretch through the car. The weekend had begun and even though we weren’t going any further than an hour or so outside the city, it was clear we were already feeling a hundred miles away.

Road Trip Route to Upstate New York

Stop 1: Lyndhurst

30 miles from Battery Park, Manhattan

About a half mile south of the Tappan Zee Bridge is Lyndhurst, one of the country’s finest Gothic Revival-style mansions. Overlooking the widest part of the lower Hudson River and the Manhattan skyline, Lyndhurst is considered one of ten homes that influenced American architectural design. Designed in 1838 by Alexander Jackson Davis, its brilliance is reflected in the history of its three owners: former New York City mayor William Paulding, merchant George Merritt, and railroad tycoon Jay Gould. With 67 acres of landscaped grounds to wander and explore, the river to drive along, and 19 elaborately decorated rooms filled with the most stunning collection of art, antiques, and elegant furniture, a visit to Lyndhurst made for a pleasing first stop on our way up to Cold Spring.

Stop 2: Stone Barns

31.9 Miles from Battery Park, Manhattan

Built by the Rockefeller Family in the 1890’s, Stone Barns is a not-for-profit organic farm and agricultural education center committed to seasonality. You may have heard of Blue Hill at Stone Barns, their award-winning restaurant where tasting menus are left entirely up to the chef’s hand. Reservations are not easy to come by, which is why we love Blue Hill Café, the farm’s casual takeaway spot for some of the kitchen’s light snacks and locally grown goodies. After carrying our lunch across the cafe courtyard to dine under a canopy of apple trees next to the historic stone barns, we drove around the farm’s expansive grounds, taking in the views of the planted fields and checking out the different livestock outposts. Whether spending the day wandering the farm, perusing their market, or traveling up for a meal at the café or restaurant, it’s an experience that is far worth the field trip every time.

Stop 3: Cold Springs

58.8 Miles from Battery Park, Manhattan

Long characterized by its walkable stretch of quaint shops and chocolate box setting, Cold Spring’s proximity to the city, picturesque waterfront, and scenic hiking trails, such as the popular Breakneck Ridge, have made it a sought-after and convenient destination for day-trippers, weekenders, and locals alike. We happily parked the car and spent the afternoon wandering up and down Main Street, taking in the mountain views and beautiful storefronts. Our first stop was to Cold Spring Apothecary and The Pantry, a pair of businesses that perfectly share a space, allowing us to easily stock up on candles and caffeine. A walk up the hill led us to Pasture, one of our favorite antique shops selling an ever-changing collection of gorgeous storied finds, and to Split Rock Books, an inviting new bookshop we could have poked around in for hours.

Stop 4: Lakeview Lodge

58.8 Miles from Battery Park, Manhattan

After an adventure-filled day with the sunroof open, there is no better feeling than pulling into that special place you will call home for the weekend. Our stay at Lakeview Lodge was a step back in time, wooing us fast with its five log bedrooms, the 1930s paneled living room, stone fireplace, antique furnishings, large screened porch, grilling patio and more. Set in the historic Cold Spring neighborhood of Valhalla Highlands on Lake Valhalla, this private community boasts swimming, boating, fishing, tennis, ping-pong, shuffleboard and mountain hiking in a private forest surrounded by a 9,000 acre State Park. High dives, pruney fingers, and aimless boat rides until the dinner bell rang… we had an absolute ball, to say the least.

ROAD TRIP MAP TO UPSTATE NEW YORK