Hike + Local Winery

We took a group of 28 NYC locals out of the city and into the Hudson Valley. The day was packed with fresh air, good conversation, and curated stops designed to make the outdoors effortless and fun.

The Highlights

A table set up in a park with a green banner that reads 'CARAVAN TRIP PLAN.' On the table, there are boxes of assorted donuts, small cups of yogurt or cream, bottled drinks, and packets of snacks. The background features a large tree, grass, pedestrians, and park benches.

A group of people waiting in line to board a bus on a city street, with a large tree providing shade. The group appears to be young adults, some with backpacks and drinks, standing on a sidewalk near a building and a street sign.

Group of people gathered around a food cart in a park with trees and greenery in the background on a sunny day.

A box of assorted bagels on a table with packages of cream cheese, small bottles of drinks, and some individually wrapped treats.

Meet Up at Washington Square Park

We met bright and early at Washington Square Park with PopUp Bagels & coffee to fuel up. After a quick hello and breakfast in the park, we hopped on the bus for the hour-and-a-half ride to the trailhead — just enough time to meet everyone on the trip!

People hiking on a forest trail surrounded by green trees.

Group of people hiking on a mountain trail with a scenic view of green hills and a winding road, holding a banner that says "Caravan Trip Plan".

Young man and woman hiking on a rocky peak with green mountains in the background, holding a green banner that reads 'Caravan Trip Plan'.

Two women smiling and posing on a rocky hiking trail in a lush green forest, with other hikers following behind them.

We started with a quick group stretch and trail overview before taking on the ~2.5 mile loop hike. The trail offered a mix of rock scrambles and open overlooks. Along the way, we enjoyed a David Bar to fuel our hike. At the top, we took in the Hudson River views

Hike Storm King Mountain

People sitting at a long outdoor table under trees, enjoying what appears to be a gathering or celebration, with many glasses of wine or drinks on the table.

A smiling woman in a black dress sitting on a wooden bench, leaning her head on a man covered in sunglasses, with a scenic view of lush green trees and rolling hills in the background.

A person sitting at a table with red umbrellas, surrounded by potted flowers and greenery at an outdoor patio of a rustic wooden building under a blue sky.

Relax at Winery

After the hike, we headed to a local winery. Here, everyone had the chance to taste four wines, enjoy brick oven pizza, and relax on the vineyard, soaking in the Hudson Valley views. The winery stop was the perfect way to wind down the day before heading back to the city.