Timber Hill Winery Wine Tastings & Bites in Milton, WI

Located in the charming town of Milton, Wisconsin, Timber Hill Winery invites visitors to step beyond the usual outdoor adventure scene and savor a unique blend of vineyard charm paired with casual conviviality. Far from the bustling tourist trails, this winery offers a relaxed spot where lush rows of grapevines frame a setting perfect for sampling local vintages and sharing good food with friends and family. Timber Hill Winery specializes in wine flights that welcome both novices and seasoned tasters, with five one-ounce pours available for a modest price, and personalized flight options to sample favorites at a slightly larger pour. Their sweet-style wines cater to palates that appreciate lighter, fruit-forward choices, setting them apart in a region known more for its hops than its grapes.

The venue itself is a spacious upgrade from typical small wineries, offering ample indoor seating and a lively bar area, although tastings are currently offered at the bar with standing room only. The patio overlooks the vineyards' freshest growth, offering a peaceful retreat to soak in warm Wisconsin afternoons. Beyond the wine, the food menu enhances the experience with artisan flatbreads, sandwiches, and a standout gigantic Bavarian pretzel, creating a thoughtful, casual pairing that elevates each sip.

While Timber Hill is a food-and-wine destination first, it fits uniquely within the local outdoor scene by connecting visitors to the land through viticulture and scenic calm. It’s a go-to for a leisurely pause after hiking or paddling nearby, or simply for those seeking a memorable wine tasting in a welcoming, unpretentious environment. The staff’s attentive service and the venue’s atmosphere make Timber Hill more than just a pit stop — it’s a place to relax, taste, and connect in southern Wisconsin’s wine country.