The best time to go to Middlebury is during the autumn months, specifically from late September to mid-October, for stunning fall foliage, or in the summer, from June to August, for pleasant weather and outdoor activities.Autumn in Middlebury is spectacular, with the surrounding Green Mountains transforming into a canvas of red, orange, and gold. This period offers ideal conditions for scenic drives along Route 7 or hiking trails like those in the nearby Green Mountain National Forest. It's a superb time for couples seeking a picturesque and tranquil getaway, perhaps enjoying a cider tasting at a local orchard or a stroll through the town's historic centre.Summer provides warm, sunny days superb for exploring Middlebury's outdoor attractions. You can enjoy kayaking or paddleboarding on Otter Creek, cycling along country roads, or visiting local farms and farmers' markets. Families will find this a great time to visit, with opportunities for activities like swimming at Lake Dunmore or exploring the UVM Morgan Horse Farm, offering educational and engaging experiences for all ages.For those looking for winter sports, December to March offers opportunities for skiing and snowboarding at nearby resorts, though the town itself is quieter during these months.