The 2 Best Wine Tours in Westchester County
Westchester County offers a surprising variety of wine-related experiences, far from the bustling city streets. Its proximity to the Hudson Valley means lush vineyards, tasting rooms, and a charming local scene that’s perfect for wine lovers. Whether you want to spend a relaxed afternoon tasting at a vineyard or combine wine with vintage shopping, Westchester has options.
In this guide, we’ll compare two standout tours: one focusing on visiting multiple vineyards in a scenic setting, and another blending wine tasting with thrift shopping and outlet visits. We’ll break down what each tour includes, the highlights, and who they’re best suited for. Expect practical details—like price, duration, and what’s included—and honest insights about what makes each one special.
Whether you’re looking for a quick wine getaway or a full day of shopping, these tours offer something memorable. Read on to find the best fit for your Westchester adventure.
1. New York Wine Vineyard Tour
The New York Wine Vineyard Tour offers a taste of the Hudson Valley’s scenic vineyards—perfect for those wanting a straightforward wine experience. For $295 per person, you get roughly 4 hours exploring 2-3 local vineyards, depending on how the day unfolds. The tour begins at Dillan’s Wine Cellar in Peekskill, a cozy spot where you’ll get a quick overview before heading out.
What makes this tour stand out? It’s all about the vineyards’ natural beauty and tasting regional wines in a relaxed setting. The itinerary includes a visit to Dylan’s Wine Cellar, a local gem that offers a comprehensive taste of Hudson Valley wines all in one spot. Since this is a small group experience, it allows for personalized attention and a focus on quality wine tastings rather than rushing through.
Though the reviews are currently blank, the tour’s simple structure appeals to those who want to avoid the fuss and focus on enjoying a handful of quality wines. It’s best suited for travelers who want a quick, immersive experience in the region’s wine culture without added activities or shopping.
Bottom Line: If you prefer a dedicated, scenic wine tour with a focus on regional flavors and a relaxed pace, this is a solid choice. It’s ideal for wine enthusiasts who want to keep it simple and authentic.
2. NY Thrift Shopping & Wine Tour
The NY Thrift Shopping & Wine Tour combines a full day of shopping and wine tasting for $399 per person, lasting around 6 hours. It kicks off at Quirkshop, a well-loved vintage and thrift store that’s perfect for picking up unique finds. After browsing 8-10 stores—rummaging through vintage, second-hand, and consignment shops—the group heads to a local vineyard for some wine and a relaxed tasting experience.
What makes this tour special? It’s more than just wine; it’s a chance to explore Peekskill’s lively shopping scene and enjoy a social outing. The tour includes a glass of wine or sangria at the vineyard, along with shared appetizers, making it feel like a casual day out with friends. The owner’s personal touch is evident, and many find the mix of shopping and wine adds a fun, unexpected twist.
While reviews aren’t available yet, the inclusive price covering gas, tolls, parking, coffee, wine, and bites suggests good value for a full day out. This tour is best for those who love to shop vintage or thrift finds, enjoy local wines, and want a leisurely, social experience.
Bottom Line: Perfect for shoppers who want to combine their love of vintage treasures with a relaxed wine experience. It’s ideal for groups, couples, or anyone seeking a mix of shopping, tasting, and socializing.
How to Choose
When deciding between these two tours, consider your priorities. If you’re mainly interested in tasting Hudson Valley wines with a scenic backdrop, the New York Wine Vineyard Tour is straightforward and wine-focused. It’s great for those with limited time or who prefer a quieter, more intimate experience.
On the other hand, the NY Thrift Shopping & Wine Tour offers a fuller day of exploration—combining vintage shopping, wine tasting, and outlet shopping. It’s suited for travelers who enjoy a lively day with varied experiences and don’t mind a longer outing.
Budget and pacing matter. The vineyard tour costs less and is shorter, while the shopping and wine combo provides more activities but at a higher price. Both tours should be booked early, especially during peak seasons like fall or summer when local events draw crowds.
Final Thoughts
Westchester County’s wine scene is a hidden gem, and these two tours showcase its best. If you want to experience the tranquility and flavors of Hudson Valley vineyards, the vineyard-only tour offers a focused, authentically regional experience. For those who want to turn their day into a lively adventure with vintage shopping, the combination tour delivers variety and social fun.
For wine lovers, the vineyard tour is a clear choice if you’re pressed for time or prefer a quiet tasting experience. If you want a more diverse day packed with shopping, socializing, and tasting, the second tour is a perfect pick.
Be sure to book early—these popular experiences fill up quickly, especially in peak seasons. Whatever you choose, Westchester’s wine and shopping scene promises a memorable outing filled with local charm.