The best time to go to Chester, Vermont, is during the autumn months of September and October for spectacular foliage, or in late spring and summer for pleasant weather and outdoor activities.For those seeking the iconic New England autumn experience, September and October are ideal. The hills around Chester explode with vibrant reds, oranges, and yellows, making it a great time for scenic drives along routes like the Okemo Mountain Road or hiking on local trails. This period also often features local harvest festivals and craft fairs, offering a taste of local culture.Late spring and summer, from May to August, offer warm, sunny days great for exploring the outdoors. You can enjoy activities such as cycling the Chester Green, fishing in the West River, or visiting nearby state parks. The weather is generally comfortable for walking around the village, browsing the antique shops, and dining al fresco.