The best time to go to Windsor is late spring (April-May) or early fall (September-October) for pleasant weather and fewer crowds.During these shoulder seasons, you'll experience comfortable temperatures, ideal for exploring the wineries and outdoor activities. The vineyards are either budding with new growth or showcasing vibrant fall colors, enhancing the scenic beauty of the region. This period avoids the peak summer heat and school holidays, offering a more serene experience for couples and those seeking a relaxed getaway.Summer (June-August) is also a popular time, offering sunny days great for poolside relaxation and outdoor events. However, temperatures can be quite warm, and attractions will be busier. For families, summer provides the advantage of school breaks, making it a convenient time to visit, with many family-friendly activities available.Winter (November-March) brings cooler, wetter weather, and some wineries may have reduced hours.