Walkway Over the Hudson & Winery Tour w/ Private Transport

A perfect combo of scenic walk and wine tasting — for those who want a taste of history and a sip of the good stuff in New York’s Hudson Valley. For $185 per person, this 6 to 8-hour private tour combines a self-guided stroll across the longest elevated pedestrian bridge in the world with visits to two of the region’s standout wineries. Your trip includes private transportation, making it all smooth sailing from start to finish.

We love that this tour offers a balance of activity and relaxation — you get your steps in on the impressive Walkway Over the Hudson, then have time to savor local wines in serene vineyard settings. Plus, the option to rent bikes (for an extra $30 per bike) allows a more energetic way to enjoy the scenery. The included instructions for your walk or bike ride are a thoughtful touch, giving you flexibility and confidence to explore at your own pace.

One potential consideration is the self-guided nature of the walk, which means you won’t have a guide narrating the scenery. However, for those who enjoy a little independence, this offers a more relaxed, customizable experience. The tour is perfect for travelers who want a mix of outdoor activity, wine tasting, and local charm, especially if they’re comfortable with a self-directed walk or bike ride.

If you’re someone who appreciates authentic local experiences, beautiful vistas, and well-curated winery visits, this tour is a great fit. It’s especially suited for those interested in self-guided exploration combined with private transport, making it ideal for couples, small groups, or solo travelers who like a bit of independence but don’t want the hassle of planning every detail.

Key Points

• Self-guided walk or bike ride across the iconic Walkway Over the Hudson with instructions provided.
• Visit two historic wineries in Marlboro and Nostrano, with tastings at each (own expense).
• Private transportation ensures a comfortable, stress-free day with flexible drop-off options, including the charming town of Beacon.
• The tour is cost-effective for the experience offered, blending outdoor activity, scenic beauty, and wine culture.
• The option to upgrade to bikes for a more energetic exploration adds flexibility.
• Ideal for those who enjoy a personalized pace and a mix of outdoor walking and wine sips.

In-Depth Review

Starting Point: The Walkway Over the Hudson

Our journey begins at the Walkway Over the Hudson State Historic Park, which is a marvel in its own right. Standing 212 feet above the river and stretching over 6,700 feet long, this bridge offers panoramic views of the Hudson River and surrounding landscape. The fact that it’s the longest and highest pedestrian bridge in the world instantly makes it a must-see, even before the wine tasting begins.

What we particularly appreciated was the self-guided approach. The instructions provided ahead of time gave us the confidence to explore at our own pace. Some travelers might prefer a guided narration, but for those who enjoy wandering freely and pausing for photos or just soaking in the vistas, this setup works perfectly.

If you opt to rent bikes (which requires prior contact and additional fee), you’ll love the chance to cover more ground and enjoy the breeze. The bicycle option transforms the experience from a simple walk to a more active, dynamic way to see the scenery. The bridge’s deck is wide enough to comfortably accommodate bikers and pedestrians, making it a safe and enjoyable activity.

First Winery: Benmarl Vineyards & Winery

After crossing the bridge, the tour takes you to Benmarl Winery, renowned as America’s oldest vineyard and holding New York State Farm License number one. Sitting on a 37-acre estate in Marlboro, NY, with views overlooking the historic Hudson River Valley, it’s a picture-perfect setting that feels like stepping back in time.

The winery’s reputation hinges on its commitment to quality and its role in elevating New York wines on the world stage. We loved how the estate combines historical significance with modern winemaking. The visit typically includes a tasting, and although the tasting itself is at your own expense, the experience of wandering through the vineyard and soaking in the serene countryside is priceless.

One of the reviews highlighted how reservations are handled in advance by the tour operator, which simplifies what can often be a complicated process. The option to include a winery lunch or additional tastings can be arranged, making it suitable for those who want an even more indulgent experience.

Second Winery: Nostrano Vineyards

Next, the tour takes you to Nostrano Vineyards, a family-run operation bursting with charm. Located in a tranquil farm setting, it’s a great place for visual memories — think rows of vines, a graceful weeping willow, and plenty of space for photos. Visitors frequently mention the delicious local cheeseboards and wines, making it an appealing stop for food lovers as well.

Reservations are handled by the tour operator, and you can upgrade the experience with additional tastings or a more elaborate meal. The relaxed atmosphere makes it feel like visiting a friend’s farm rather than a commercial operation, which many visitors find refreshing.

Optional Stop: Beacon

For those taking the train back to New York City, the option to be dropped off in Beacon is a thoughtful addition. This artsy town offers shops, eateries, breweries, and a relaxed vibe to wind down your day. The proximity of the train station to Main Street makes it easy to explore or catch your ride home.

Practical Details and Value

The entire experience starts with private transport, which relieves the stress of navigating or finding your way between locations. The self-guided walk allows you to tailor how much time you spend on the bridge — whether you take it slow for photos or hire bikes for a quicker, more energetic experience.

At $185 per person, the tour offers excellent value considering the private transport, the scenic walk, and the two winery stops. You’ll want to budget extra for wine tastings and any gratuities for the driver or winery staff, especially since some wineries automatically add a 20% gratuity.

The tour runs year-round, with open hours from noon to late evening, so you can plan a visit during most seasons. The confirmation process is straightforward, and the free cancellation policy provides peace of mind if your plans change.

What We Liked and What to Consider

We loved how flexible and personalized the experience felt. The stunning views from the bridge and the historic charm of the wineries make for memorable moments. The private nature of the tour means it can be tailored to your pace, avoiding the crowded group feel.

A minor consideration is that since the walk is self-guided, some travelers might prefer a guided narration or more structured experience. Also, the additional costs for bike rentals, tastings, and gratuities can add up, so it’s wise to plan your budget accordingly.

Who This Tour Suits Best

This experience is perfect for adventurous wine lovers who enjoy scenic outdoor activities, or for couples and small groups seeking an intimate, flexible day in the Hudson Valley. It’s ideal for travelers who appreciate history, landscape, and wine, and prefer a self-paced itinerary over guided tours. If you’re comfortable with a bit of planning and enjoy a mix of physical activity and leisure, this tour will suit you well.

Frequently Asked Questions

Is the walk across the Walkway Over the Hudson self-guided?
Yes, the walk is self-guided, with instructions provided beforehand to help you navigate and enjoy the views at your own pace.

Can I rent bikes instead of walking?
Absolutely. Bike rentals are available for an additional $30 per bike, but you’ll need to contact the tour operator in advance to reserve.

Are wine tastings included in the price?
No, tastings at the wineries are at your own expense, but the tour handles reservations. Many wineries charge for tastings, and some include gratuity automatically.

What is the drop-off location in Beacon?
If you choose to end your tour in Beacon, you’ll be dropped off on Main Street, close to shops and eateries with a short walk to the train station for your return trip.

Is this tour suitable year-round?
Yes. The tour operates daily from noon to late evening, weather permitting. It’s a great way to enjoy the views in any season.

How long does the entire tour last?
Expect about 6 to 8 hours, depending on your pace and how long you spend at each stop.

Final Thoughts

This Walkway Over the Hudson and Winery Tour offers a compelling blend of natural beauty, history, and local flavor. It’s a smart choice for travelers who want an independent, relaxed experience without sacrificing comfort or quality. The private transportation ensures ease, while the self-guided walk and winery visits give you flexibility to tailor the day to your interests.

For those seeking a laid-back yet engaging way to explore the Hudson Valley, this tour hits the right notes. It’s especially suited for small groups, couples, or solo travelers who love good food, scenic vistas, and a touch of adventure. With its combination of iconic views and delicious wines, it promises a memorable day in one of New York’s most charming regions.