Frank Sinatra said if you can make it in New York, you can make it anywhere. So, why would anyone ever want to leave? Granted, New York may be the greatest city in the world. But, sometimes, it’s helpful to escape its busy streets to hear what the Atlantic Ocean has to say or sway with the trees in upstate New York.
If you’re ready to pack your weekend bag and board a train to somewhere new – or be somebody new – just for a day or two, any one of these destinations will be happy to whisk you away.
Fire Island, New York
Fire Island is where people go to fully escape the sights and sounds of the city, but still be near enough to get back home for work on Sunday. As a barrier island to Long Island, it’s easy enough to ferry your way to some fiery fun.
Fire Island Pines is a nice part of the island to walk around, shop, and enjoy a meal or two. You’ll have many beach options here, but Kismet Beach tends to be a quieter corner of the island. It’s family-friendly and you can even play a game of tennis while the kids enjoy the playground.
The Hamptons, New York
Which brings us to, of course, the Hamptons – where everybody who’s anybody escapes to in the summer. With so many beaches and hamlets to choose from, it’s tough to know which stop to get off on the Long Island Railroad.
A safe bet is Montauk because of its beautiful lighthouse. Sag Harbor is also a viable option if you need a little retail therapy. To visit most of the beaches, you need a permit, which can take the fun out of a peaceful, easy weekend.
Coopers Beach, however, is open to the public. So, if you’re looking to dip your toes in the sand, that may be your best bet. To help you plan this trip to perfection, here’s a guide to the top things to do in the Hamptons.
Cape May, New Jersey
Pretty little Cape May. This is the place to come to stroll past old Victorian homes, breathe in the salty, fresh air, and dine on some of the finest dishes this side of heaven.
Congress Hall is probably one of the most notable locations in this small slice of paradise. If you can splurge on a room here, you’ll be treated to afternoon cocktails by the sea, plush bedding, and a delectable on-site restaurant, The Blue Pig Tavern.
Philadelphia, Pennsylvania
Further past Jersey, you can drive or take the train to Philly for a nice long weekend in another city with an equal amount of grit. Stay right in the heart of downtown so you can go on a Philly cheesesteak spree and enjoy all the finer things the city has to offer.
You can get a gander at the Liberty Bell, run up the steps with Rocky, or saunter through the Philadelphia Museum of Art. If you make your way over to Rittenhouse Square, there’s a lovely restaurant called Parc which will be happy to serve you some French culinary sensations.
Bear Mountain, New York
As we enter into the fall, if you feel like you’ve missed beach season, you can start to head north to a few different mountain destinations. Bear Mountain is an easy drive at just over an hour north of the city.
See if you can tuck into the Bear Mountain Inn for a few nights to lap up their luxury accommodations and beautiful on-site spa. If you plan this trip when the leaves start changing, you’ll have your very own fall paradise.
Beacon, New York
In and around Bear Mountain, you’ll find plenty of adorable little towns where the loudest thing you’ll hear at night are the crickets. Beacon is one of them.
With art galleries, coffee shops, and homegrown boutiques, it has a lovely old-world feel to it, while still being modern, hip, and cool. While you’re here, be sure to check out Hudson Beach Glass on Main Street before ordering a double espresso from Big Mouth Coffee Roasters.
Cold Spring, New York
Cold Spring really gives Beacon a run for its money. Try them both out on two separate occasions to see which one you like more. Like something straight out of a Hallmark movie, Cold Spring will charm you the moment you step foot onto Main Street.
As an easy train ride up the Hudson line, you’ll also take in those decadent Hudson River Valley views all along the way. When you make it to Main Street, all you have to do is stroll. With art galleries, antique shops, and eateries galore, you won’t run short of things to do.
Le Bouchon has everything from escargot to cassoulet. The Foundry Rose is a great way to start your day with a hearty omelet. Meanwhile, Cathryn’s has a spectacular wine list and an eclectic menu. Also, be sure to pick up a trinket or two at the Cold Spring General Store before you leave.
Hudson, New York
There’s a wonderful creator on YouTube named Kevin Lee Jacobs. He lives in a gorgeous historic home in Hudson and teaches us how to cook easy dishes, grow the perfect garden, and enjoy the simple pleasures in life.
He, like many others, used to live in the city but moved out about twenty years ago to enjoy a different kind of lifestyle. Now, he entertains friends on the weekends, visits farmers’ markets, and enjoys the offerings of this quaint little town.
Watch his videos for a little inspiration. You’ll quickly find yourself researching local Airbnbs, hopefully in one of those gorgeous historic homes.
New Paltz, New York
A little further up the line, you have New Paltz, New York, which is an adorable town in its own right. But, that’s not where we’re headed with New Paltz in our sights.
We’re headed to Mohonk Mountain House, a sprawling lakeside resort with decadent suites and even more spectacular grounds. You could spend the entire weekend on the property, enjoying spa services and meals, and taking in that beautiful New York mountain life.
Lake Placid, New York
You can probably see where we’re going with this. Further, yet, up the line, we have the picture-perfect town of Lake Placid. This is an especially beautiful town when it’s coated in snow.
Rent a nice Airbnb near Main Street so you’re in close proximity to all its colorful cafes, shops, and restaurants. If, instead of the winter, you make this a summer retreat, then you only need to set your sights on one thing: Mirror Lake. Rent a kayak, lean back, and watch the clouds roll by.
Boston, Massachusetts
Let’s branch further out of the state and consider a few other cities that certainly aren’t New York, but still have plenty of pizazz.
In Boston, you can stroll the cobblestone streets of Beacon Hill, spend all your money in the shops on Newbury Street, and fill up your Airbnb with wine and cheese from Faneuil Hall Marketplace.
As a harbor town, there’s plenty of fresh air to breathe in while you enjoy some delicious clam chowder and get a sense of what some of the smaller, but no less exhilarating, cities in America feel like.
Cape Cod, Massachusetts
Of course, Cape Cod is a glorious summer retreat, for obvious reasons. But, it’s also inviting in the fall and winter when everything’s a little more sleepy.
Like the Hamptons, there are plenty of different towns to explore on the Cape. Hyannis is popular, as is South Chatham. But, there’s one secret little corner, Woods Hole, with a lovely inn right on the water.
If you book a room in the Woods Hole Inn, you’ll be perfectly placed to do nothing more than stroll past the sea, enjoy some delicious meals, and allow your body to go into full relaxation mode.
Enjoy Your Weekend Getaway
There we have it! You can truly have it all when you sneak away for a long weekend and then return home to, quite possibly, the greatest city on earth.
Whether you’re headed to the Hamptons or Philly, we have a destination guide to help you plan your two or three days to perfection. Here’s hoping we meet you out on the streets of New York someday!