The Perfect Fall Day Trip from NYC Does Not Exi– Oh Wait, I Just Found It

This year, I opted to use Blacklane, which offers reliable chauffeur services from the city. This isn’t your typical car service—it’s much easier and much more convenient. I’m able to book and plan my entire day trip on the app, with full transparency in pricing (which is extremely reasonable), vehicle type (my friend group of four opted for a super comfy Business SUV) and duration.

Mapping out what some might call the perfect fall day trip from NYC (yes, I’m bragging), my friends and I threw on our flannel and puffy vests (just kidding) and awaited our SUV.

Blacklane’s friendly and knowledgeable driver picked us up at my doorstep in Manhattan. Our first stop? Milea Estate Vineyard in Staatsburg. Wine aside, the Milea views of rolling hills full of gorgeous grapes are top notch. After a delicious wine tasting (allow me to recommend the 2024 Queen of the Meadow Rosé) and a few shared bites for the table, we snapped photos in front of the highly Instagrammable pink wall, bought a bottle of said rosé for later and hit the road.

Then we headed to Bad Seed Cider Taproom in Highland. Though we all loved the boozy cider and beer selections on tap, our gluten-free friend was particularly thrilled to be able to indulge as well (he usually has to sit things out if we make a brewery stop). We (okay, I) smartly checked the Bad Seed calendar in advance, so we knew we’d be encountering a lively queer fall family festival, featuring food trucks, live music and pumpkin picking.

Afterwards, there was still time for a stop at Brotherhood, America’s oldest winery, in Washingtonville. Brotherhood boasts grape stomping for those who want a little late afternoon workout.

We wrapped things up with an outdoor dinner in Tarrytown at one of our favorite haunts, River Market Bar & Kitchen. I opted to end our Blacklane journey there so that we could sit and have a leisurely meal (with the option to keep the Tarrytown party going if we wanted). There’s a convenient train station located adjacent to River Market for a quick city return. But it would have also been an easy option to extend my trip and have our driver drop us back at my front door.

Were we exhausted after our perfect fall day trip? Absolutely, in the best way possible. Were we tipsy while we scrolled through the day’s photos on our short trip home? Again, yes. Will we be using Blacklane and heading north for fall fun again next year? I think you already know the answer.