Top 2 Wine Tours In Westchester County

Westchester County isn’t just a suburban escape; it’s a surprisingly vibrant spot for wine tours. Its proximity to New York City makes it an accessible choice for a day trip, and its scenic landscapes of rolling hills and lush vineyards create a perfect backdrop for tasting some of the region’s best wines. This guide will introduce you to two distinct experiences: one that combines thrift shopping and wine with outlet shopping, and another focused entirely on visiting Hudson Valley vineyards. Expect a mix of casual tasting, shopping, and scenic drives—each offering its own flavor of Westchester.

Whether you’re interested in a longer, multi-stop day that mixes vintage shopping with wine, or prefer a shorter, wine-focused trip that visits a handful of vineyards, there’s something here for every kind of traveler. I’ll walk you through what makes each tour unique, who it’s best suited for, and practical tips to help you choose the right experience.

Quick Overview

This list features two tours in Westchester County. The first mixes thrift and vintage shopping with a vineyard visit and outlet shopping, providing a full-day experience for those who want variety. The second is a shorter, focused wine vineyard tour that visits 2-3 local vineyards, perfect for a more relaxed half-day outing. Both tours are customizable in the sense that they include key stops and tastings, but they differ significantly in scope and price, offering options for different schedules and interests.

1. NY Thrift Shopping & Wine Tour

At $399 per person for about six hours, this tour combines shopping and sipping in a way that’s hard to beat for lovers of both. Your day begins at the Quirkshop, where you’ll browse 8-10 shops, ranging from thrift to vintage and consignment stores. After this retail therapy, the group heads to one of the tour organizer’s favorite local vineyards, where a glass of wine or sangria awaits you. The experience also includes shared appetizers from the vineyard kitchen, making for a relaxed, social atmosphere. The tour fee covers gas, tolls, parking, coffee, wine, and bites, so there are no hidden costs.

What makes this tour stand out is its variety and sense of exploration. You get to hunt for unique finds in Westchester’s eclectic shops, then unwind with a wine tasting in a scenic vineyard setting. The shopping stops are handpicked, and the vineyard visit offers a chance to learn about local wine production. Final bonus: the tour concludes at the Woodbury Commons Outlets for those wanting some retail therapy of a different kind.

Bottom line: This is ideal for travelers who enjoy a bit of everything—shopping, wine, and a lively group atmosphere—and are comfortable with a longer, more varied day.

2. New York Wine Vineyard Tour

Priced at $295 per person for roughly four hours, this tour offers a more focused experience. Starting at Dillan’s Wine Cellar in Peekskill, you’ll visit 2-3 local vineyards, with the itinerary dependent on the day’s schedule. This trip emphasizes the scenic beauty of the Hudson Valley and the art of wine tasting, without the shopping component. Tours typically include tastings at each vineyard, giving you the chance to sample a range of regional wines.

This tour is perfect if your priority is wine and scenery. The host, Dillan’s, is a well-known local spot that allows you to taste Hudson Valley wines in one place before heading out. It’s a straightforward, relaxed outing suited for those who want to explore the region’s viticulture without extra stops or shopping. The shorter duration makes it accessible for an afternoon or a half-day activity, and since the admission is free at Dillan’s, you only pay for the actual tastings and transportation.

Bottom line: Best suited for wine enthusiasts who want to experience the region’s vineyards without a full-day commitment, and who prefer a quieter, more intimate setting.

How to Choose

When deciding between these two options, consider your priorities. If you’re interested in a full-day adventure with shopping, wine, and maybe some outlet deals, the NY Thrift Shopping & Wine Tour offers the best value for variety. Keep in mind, it’s a longer day with more moving parts, which might not suit everyone.

If your main focus is sampling local wines in a scenic setting, then the New York Wine Vineyard Tour provides a relaxed, focused experience that’s easier to fit into a busy schedule. It’s also slightly less expensive, making it attractive for budget-conscious travelers.

For booking, consider the season—spring and fall are especially beautiful for vineyard visits, with lush landscapes and crisp air. Also, reserve early, especially for weekends, as these tours tend to fill up quickly.

To sum it up, Westchester County offers diverse ways to enjoy wine, whether through a bustling shopping and tasting day or a serene vineyard visit. For a full experience that combines retail therapy with wine, the NY Thrift Shopping & Wine Tour is a fantastic choice. If you prefer a shorter, more focused wine tasting adventure, the New York Wine Vineyard Tour hits the mark. Both provide a taste of the region’s local wines and charming countryside, so think about your schedule, interests, and what kind of day out you’re craving.

No matter which you pick, booking early will ensure you don’t miss out on these memorable experiences. Cheers to discovering Westchester’s hidden wine gems!