Four Fabulous Road Trips from NYC

Well we did it. We left our NYC bubble for a road trip last week in honor of my husband’s birthday and it was equal parts normal and surreal. We dined indoors, stayed in hotels and rented a car for the first time in a looong time. Of course, all of these everyday occurrences came with necessary adjustments.

I have only set foot outside of Manhattan (i.e. to Brooklyn) a couple of times since March and to be honest, I was more nervous than I expected for our first overnight adventure. As scary as it was to be here in March and April (ambulances and sirens still make me jump) I felt completely safe here in our NYC bubble. We got to know our neighbors better, checking in on each other and listening to the music, clapping and banging pots each night at 7 p.m. Our appreciation grew each week for the businesses that stayed open so we could get our essentials when delivery options were nonexistent. We learned to give each other space to protect each other.

It felt strange to take a trip when in so many parts of this country it still isn’t advised. But the progress this city — and state — has made is nothing short of extraordinary. Traveling throughout Long Island and upstate New York last week only confirmed how seriously all New Yorkers have taken the pandemic. Every town we stopped in, large or very very small, was practicing social distancing. There were signs posted everywhere to wear masks and people were following rules without causing a fuss. We really banded together because we knew the only way out of this was together.

We’re leaving soon (I think) but NYC will always be endgame for us. No matter what diversions we take, we know this city — this state — will always be part of our story. Man, if you think I’m sappy now just wait for the post when we actually move away!

If you’re in NYC now or planning a future trip and are interested in seeing more of the state, here are four fabulous destinations to check out on your next road trip:


The first stop on our trip last week was Huntington, on Long Island. It took us only an hour to drive from our front door in Manhattan to Oheka Castle, where we stayed for three nights. I first saw this historic home on Succession (the best) and when I learned it was a hotel, I knew I had to stay there. It was a lovely place to relax while Craig was out golfing. I walked the grounds, read in the library you see here and enjoyed the serene country setting. No ghost sightings, thank god.

Looking for water? From Huntington, you’re only a 30-minute drive south to Jones Beach or 30 minutes north to Bayville on the Long Island Sound.


Last October we drove all the way to the “end of the world” in Montauk, the most Eastern point on Long Island. From the moment we settled into our condo at the Surf Club, I was obsessed. Ocean views, sandy beaches and so much good food nearby. We explored the Hamptons, toured the famous lighthouse and had a fantastic meal at Scarpetta Beach. I’ve already told Craig we’re retiring on Long Island, which didn’t surprise him since Something’s Gotta Give is my favorite movie and Diane Keaton is my high priestess.

I have to say, going after the summer season ended was well worth it. Cheaper rooms and no crowds? Yes please.


We’ve been lucky enough to visit friends in Rhinebeck a few times. And last Thanksgiving, we were even able to borrow someone’s home since we weren’t heading to Michigan or Arizona to see family. It’s such a cute town that only takes a couple of hours drive or train ride. Think true New England charm: cozy restaurants, lots of antique shops and plenty of quiet. If you haven’t noticed yet, I like a historic home and this one boasts a Vanderbilt mansion nearby open to tours (seeing it decorated for Christmas was lovely) and America’s oldest inn.

You can also stroll Poets’ Walk Park in nearby Red Hook, which is also home to one of my favorite Italian spots, Mercato.


For our second stop last week we got to enjoy the picturesque scenery of the Hudson Valley on our way to Cooperstown, home of the National Baseball Hall of Fame and Museum. My husband is a huge baseball fan and I really enjoy the game and the history behind it. So when we decided to rent a car, we knew we had to make a trip up there. Cooperstown looks like a postcard full of B&B’s, charming restaurants and too many baseball memorabilia shops to count. We really enjoyed our stay at the Landmark Inn and happily gobbled down the last two lobster rolls at Mel’s at 22.

You definitely don’t have to be a baseball fanatic to enjoy this gorgeous little town. And bonus: You can also convince your partner to stop at Woodbury Common on the way back.

Being able to travel is always a luxury and one that feels especially precious now. Taking the time to explore your home state or wherever you’re calling home right now really makes you appreciate your surroundings. I know we have more adventures in our future far from here but am so glad we will leave with a more complete picture of all New York has to offer.


You may also like


Leave a Reply