New York to Montreal Road Trip: Where Past Meets Present

Whether exploring the Great Camps of the Adirondacks, cheering on your horse at Saratoga Springs or biking amongst the outdoor exhibits of a forward-thinking art center in Hudson Valley, this New York to Montreal road trip balances the glamor of an era gone by with the area’s forward-thinking, contemporary heart.

The Catskills and Hudson Valley

Days 1 & 2

Leave New York City behind as you venture into the bucolic Hudson Valley just a few hours drive north of the big city. Thanks to generations of artists escaping the city to find inspiration in nature upstate, Hudson Valley is awash with trendy boutiques, fantastic restaurants and acclaimed art institutions.

Indulge in a farmer-led visit and lunch at the renowned Stone Barns Center for Food & Agriculture, then stop by Storm King Arts Center to explore this leading open-air museum by bike. At the end of the day, rest your head at Troutbeck– a beautiful 250-acre estate that has hosted naturalists, poets and other romantics of the likes of Emerson and Hemingway.

On your second day, Troutbeck has a myriad of activities to immerse you in the surrounding forests and valleys that have long inspired its visitors. Whether you’re interested in hiking, a guided fly-fishing experience or meditation, there’s something for everyone.

Saratoga Springs

Day 3 & 4

Continue to step back in time as you venture further upstate. First, you’ll stop by Olana Estate, home to one of the major figures in the Hudson River School of landscape painting, for a private tour through the historic building and sweeping grounds. Then it’s onward to Saratoga Springs, where you’ll enjoy the nostalgic glamor of thoroughbred horse races. We’ll arrange your VIP box seats at the track with a private paddock pass and access to the winner’s circle. Don your race day best (don’t forget your hat!) and hope the odds are in your favor.

The Point in the Adirondacks

Days 5-7

Continuing north, you’ll drive a few hours to enter the Adirondacks. This wild landscape sprawls across over 6.1 million acres of beautifully rugged mountains, lakes and natural beauty. Soak in your beautiful surroundings with cocktails from the epic vantage point of the Lake Placid Olympic Ski Jump.

Enjoy the best of this beautiful wilderness from the comfort of The Point, a secluded luxury property on Saranac Lake. The Point is a true vestige of the past and a member of the elite ranks of the “Adirondack Great Camps.” In the early 19th century, Gilded Age magnates– such as the Vanderbilts and Guggenheims– built idyllic log mansions along the lakeshores of upstate New York as much-needed escapes back into nature. The Point, built by a member of the Rockefeller clan, is the paragon of this Great Camps era and continues to promise the offer of peace and natural beauty to this day.

During your luxurious stay at The Point, unwind without the distraction of television and with the serenity of the lake and forest at all sides. Twice a week you’ll have the opportunity to dress up in formal attire and join an elegant seven-course meal, in the glamorous style of the Rockefeller’s Great Camps of old. During the day, participate in as many (or as few!) activities as you choose– from waterskiing, fishing and paddle-boarding on the lake to hiking, tennis or croquet amongst the trees.


Days 8-9

Finish off your journey by crossing the Canadian border into Montreal, the cosmopolitan heart of Quebec. This city is a convergence of the Old and the New World, the French and English language, exciting new ideas and centuries of history. Your accommodation at the Hotel William Gray mirrors the dichotomy of the city itself with its unique blend of modern design and historic architecture.

Walk the cobblestone streets of Old Montreal with a local historian and peel back the layers of time as you discover the city’s journey from a 17th century fur-trapping town to the multicultural hub it is today. Alternatively, get a taste of Montreal’s multicultural influences on a food tour of North America’s largest open air market with a local chef.


Day 10

Time to head home! You can fly from Montreal or choose to make the long haul driving back to New York City (6 hrs).

From The Magazine


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