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This region features the Ascutney Mountain resort (closed for the 2011-2012 ski season; future opening has not yet been determined), a ski area in West Windsor that has been in existence for over 60 years. (Skiers and riders found a mountain with a summit elevation of 2,520 feet, 57 trails, and six lifts. There are 150 acres of trails and 50 acres of tree skiing and glades.)

In the summer, there are hiking trails in the region, including one to the peak of Mount Ascutney, as well as the Summit Road to drive to the top, in Ascutney State Park. Canoe, kayak and rowboat rentals are available at Wilgus State Park on the Connecticut River. Small ponds in the area open to the public include Mill Pond and Stoughton Pond. For river and other outdoor adventures Great River Outfitters offers year round outings for all ages and skills.

The large town of Windsor has many shops and dining establishments. It also is home to the American Precision Museum, housed in a refurbished armory, it has the largest collection of historically significant machine tools in the nation. Another family-oriented destination in Windsor is the Path of Life Sculpture Garden, which includes an 80 hemlock tree maze and a stone labyrinth. It is open year round.

Windsor was one of the first major towns in Vermont, and was where, in 1777, a constitution of the "Free and Independent Republic of Vermont" was adopted. The Republic existed for 14 years, before Vermont was admitted to the Union as the 14th State. History buffs will want to visit The Old Constitution House where the Vermont Constitution was drafted. Also in Windsor is The Windsor House, listed on the National Register of Historical Places.

The historic, upscale town of Woodstock is a short drive from this region, as is the Okemo Ski resort in Ludlow.

The Ascutney Mountain region is just off Interstate 91, and Amtrak operates a train between New York and Montreal that stops in Windsor. Airports within two hours include Burlington, Manchester, NH and Hartford, CT.