Hudson Valley Wine and Walkway Tour

The Hudson Valley is one of the oldest wine-growing regions in the country, and the Highland-Marlboro area on the west bank has a cluster of wineries within a short drive of the Walkway Over the Hudson. This tour provides private transport between the Walkway and several tasting rooms, so you can sample wines without worrying about who drives. It is a small-group format that suits couples and friends, and the itinerary can usually be adapted a little to your interests. Check the product page for the stops, the number of tastings and any minimum group size.

The region's wine story goes back centuries, helped by the river's moderating effect and the slopes of the Shawangunk and Highland ridges. Producers range from long-established family wineries to newer tasting rooms with views over the river and the orchards. Hudson Valley wines include hybrids and cool-climate varieties that do well in the area, and tasting rooms often add cheese, cider or snacks. A guided day with private transport means you can try several and still enjoy the walk across the bridge.

The Walkway adds a very different note to the day. A morning walk over the river works up an appetite and gives the scenery that most tasting rooms only suggest. Following it with a series of tastings on the west bank, where vineyards, orchards and farm stands fill the roads, makes a well-rounded day. Brotherhood Winery in Washingtonville, often described as the oldest continuously operating winery in the country, is a bit farther afield, but the region's wineries are full of history and character.

Before you book, check how many wineries are included and how long you spend at each, because tours vary. Tastings usually carry a fee, so ask what is included in the price, and tell the operator about dietary needs or mobility limitations. Wear comfortable shoes for the Walkway and bring a light jacket, since the bridge is windy. Weekdays are quieter, autumn is beautiful and spring is a good time to avoid the crowds.

Responsible tasting matters on a day like this. Pace yourself, drink water between pours, and eat a proper lunch, ideally at a winery with a kitchen or a nearby farm stand. Most tasting rooms offer small pours, and many will happily share a tasting among two people if you ask. If you buy bottles, the driver can usually store them safely in the vehicle, and some wineries will ship to your home state, though shipping rules vary by state and are worth checking in advance.

Planning ahead pays off. Ask the operator whether there are vegetarian or alcohol-free alternatives, how the pickup is arranged and whether children or non-drinking friends can join the transport. Mention any celebration, because tasting rooms sometimes arrange a private table, and check the weather so you can dress for both the open Walkway and the sheltered tasting rooms.

Finally, remember that the Hudson Valley's tasting rooms vary in style, from rustic barns to polished estates with terraces, so ask which kinds your itinerary includes and whether any have a kitchen. Note also that some smaller producers open by appointment only in the quieter months, and that harvest season brings a livelier but busier atmosphere.