Vermont is an outdoor enthusiast’s paradise and the call of nature can be somewhat irresistible. The Green Mountain State is home to more than 700 miles of hiking trails. Nestled between the Taconic and Green Mountain Ranges, Dorset offers unparalleled opportunities for outdoor recreation – whether that’s hiking, mountain biking, kayaking, or canoeing in the summer or snowshoeing and cross-country skiing on fresh powder in the winter months. 

Whether you’re looking for an easy, family-friendly hike or want to spend the day in the clouds with jaw-dropping views, it’s at your fingertips here in Dorset. If there are only five hikes you ever do in the region – make them these.   

Owls Head Town Forest

The Town was gifted 30 acres on top of Owls Head in 1963 by the Dorset Science Club. More than 50 years later, the Town of Dorset purchased an additional 260 acres, allowing them to partner with organizations like Vermont Youth Conservation Corps., the Vermont Land Trust, and the Dorset Historical Society to expand Owls Head Town Forest and develop an expansive trail network that illustrates the historic, cultural, ecological, and recreational values of the Town Forest. 

The Town Forest Trail is located just off the beaten path on Vermont Route 30 in Dorset. The possibilities for hiking here are endless. 

We recommend the Gettysburg Quarry Hike. This nearly half-mile hike includes an elevation change of 800 feet, making it perfect for intermediate hikers. This steady ascension brings you to the lesser-known quarry in Dorset. Just before the quarry is a side trail that leads to the lookout, where you can take a seat on Art’s Bench and enjoy the vista views. Need something quick and easy? The journey to Lower Prince Quarry takes just 30 minutes and is a solid option for those looking for an easy hike. This quarter-mile hike along mostly flat terrain leads you to a small view point to the west, with the Quarry to your east. 

Looking for a greater challenge? Try the hike to Gilbert Lookout. At 1.6 miles and an elevation gain of more than 1,200 feet, this trek isn’t for the faint of heart. This trail extends beyond the Gettysburg Quarry, leading to a rock ledge with views of the Adirondack Mountains.

The Pinnacle

Replicating a ruin from the English countryside, this stone structure has sat atop a hill towering over Dorset Village for more than 100 years. The Pinnacle property, which includes 35-acres of forested land and several acres on the adjacent hill, is easily accessible – and at just one mile with a slight elevation gain of 250 feet, the perfect fit for those looking to spend an hour in nature. Located near Route 30, Dorset Hollow Road, and Peace Street, this stunning property was acquired by the Town of Dorset in 2005. 

Cutler Memorial Forest

Located off Peace Street near the Dorset Village, this property was generously given to the Town of Dorset in 1976 by resident Isabelle Cutler. The land features quaint walking trails and a small bridge crossing the Mettawee River. You can hike the entire property in about 45 minutes and the land includes both flat grounds and small, rolling hills.