Brotherhood Winery has the kind of history that’s hard to fake — it’s America’s oldest continuously operating winery, and the underground cellars still feel like stepping back in time. A short drive from Lake Lodge Retreats, it makes for a relaxed half-day out: a guided tour through the original 19th-century stone cellars, followed by a tasting flight that covers everything from crisp whites to bold reds. The grounds are lovely too, with gardens and courtyards that are easy to wander between tastings, and it’s a genuinely good fit for a group celebrating something — a milestone birthday, an engagement, a girls’ weekend — without needing to plan much beyond showing up. Tastings can be booked in advance for larger groups, which is worth doing if your party is more than four or five. Afternoons tend to have the best light for photos in the cellar and gardens, while weekends bring a livelier crowd if that’s the vibe you’re after. It pairs naturally with the area’s wineries the Hudson Valley is known for, and gives a Lake Lodge Retreats weekend a slower, more indulgent afternoon between lake days.
