If you are looking for the perfect day trip, Brotherhood Winery offers an unforgettable experience steeped in history. As America’s oldest continuously operating winery, its 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.
To truly appreciate Brotherhood Winery, you have to understand the roots that run deep beneath Washingtonville, New York. Founded in 1839 by a European immigrant named Jean Jaques, the winery began under a simple premise: crafting quality wines from local grapes. Jaques dropped his first roots into the rich Hudson Valley soil, utilizing the naturally temperate microclimate created by the nearby Hudson River.
By the mid-19th century, the winery had expanded significantly. Its underground hand-excavated stone cellars—which still stand today as the oldest and largest in America—were dug out to provide a naturally regulated climate for aging wine. Remarkably, the winery survived the devastation of the Prohibition era in the 1920s by pivoting its business model to produce sacramental wine for religious ceremonies and medicinal tonics. This resilience earned Brotherhood Winery its rightful title as America’s Oldest Winery, a badge of honor it wears proudly to this day.
When you pull up to the cobblestone courtyard of Brotherhood Winery, you are greeted by an estate that feels distinctly European. The centerpiece of any visit is the famous Underground Cellar Tour. Led by knowledgeable guides, these tours take you deep beneath the surface into vaulted stone tunnels lined with massive oak casks, some of which have been resting in place for over a century. The air is cool, damp, and heavy with the scent of aging oak and fermenting grapes—a sensory journey back to the 1800s.
Following the tour, visitors are treated to a curated tasting flight. Brotherhood Winery splits its selections into distinct tiers, ensuring there is something for every palate:
The Traditional Flight: Showcasing historic New York varietals and sweet/spiced options like their famous May Wine.
The Premium Flight: A collection of dry, sophisticated estate-grown vinifera wines, including crisp Chardonnays, bold Cabernet Sauvignons, and elegant Pinot Noirs.
The Sparkling Selection: Perfect for celebratory toasts, featuring local method-traditionelle sparkling wines.
Conveniently located just a short, scenic drive down the road from Monroe, Brotherhood Winery pairs effortlessly with a weekend stay at Lake Lodge Retreats. Whether you are seeking a break from outdoor lake activities or looking for an elegant rainy-day excursion, this destination fits the bill seamlessly.
To make the most of your excursion, keep these visitor tips in mind:
Reservations are Key: While walk-ins are accommodated when possible, tour spots and tasting reservations fill up rapidly, especially on crisp autumn weekends. Book online via their official channel before heading out.
Dress in Layers: Even if it is a blistering 90°F summer day outside, the historic underground cellars maintain a constant, chilly temperature between 50°F and 60°F year-round. A light jacket or sweater is highly recommended.
Group Accommodations: Traveling with a larger crowd for a milestone birthday or a girls’ getaway? Coordinate with the winery ahead of time to secure a private group tasting table in the courtyard or the Grand Monarque Hall.
Beyond the wine itself, the estate grounds invite you to slow down and linger. After your tasting, grab a full glass or a bottle of your favorite vintage and claim a spot in the outdoor courtyard. Surrounded by historic brick architecture, manicured gardens, and bubbling stone fountains, it provides an idyllic backdrop for conversation and photography.
If you get hungry during your visit, the winery grounds frequently host local food trucks on the weekends, or you can step into the onsite restaurant and cafe spaces to enjoy artisan cheese boards, wood-fired pizzas, and seasonal flatbreads designed specifically to complement the wine menu.
Before heading back to Lake Lodge Retreats for a relaxing evening by the water, be sure to stop by the expansive Brotherhood Winery emporium and gift shop. It is a treasure trove of local New York products, specialized barware, custom gift baskets, and, of course, the full portfolio of Brotherhood wines.
Whether you opt for a bottle of their historic spiced Holiday Wine to enjoy by a winter fireplace, or a crisp, chilled Sauvignon Blanc to sip on the lodge deck during a summer sunset, bringing home a bottle is the perfect way to extend your Hudson Valley experience long after your vacation comes to a close.
