Hiking in Southern Vermont
Southern Vermont is known for its beautiful scenery, and one of the best ways to enjoy it is hiking on one of the many area trails. Whether you want a challenging mountain climb with the reward of endless views, a secluded hike in the green trees, or a just a short easy walk through town, there is a trail here for you!
Here are a few of our favorite hikes, or check out our Hiking & Biking directory for all the trails in the area.
Mt Olga Fire Tower
A short, rewarding hike from Hogback Mountain Overlook leads to the Mt. Olga Fire Tower. This is one of Southern Vermont’s best-kept secrets. For a quicker route, take the Tower Trail behind Metcalf Distillery. It’s a 0.6-mile hike with about 200 feet of elevation gain and passes through remnants of the old Hogback ski area. For a longer, scenic option, start from Molly Stark State Park. That route is a 1.8-mile loop through peaceful, mixed forest.
Regardless of how you get there, climb the fire tower at the summit for panoramic views. You’ll see Vermont, Massachusetts, and New Hampshire from the top. It’s a short adventure with a big payoff, perfect for families or a scenic break on Route 9.
Horace Hill Recreation Area
Horace Hill offers a peaceful yet invigorating hiking experience for outdoor enthusiasts of all levels. This new multi-use recreation area boasts gently winding trails through hardwood forests of West Dover. Whether you’re looking for a quiet nature walk or a moderate uphill climb, Horace Hill delivers a perfect blend of natural beauty and New England charm. Ideal for locals and visitors alike, it’s a must-visit for anyone craving fresh air and quiet trails.
Valley Trail in West Dover
The Valley Trail is a scenic pedestrian and bicycle pathway that connects the towns of Dover & Wilmington. This 5 mile trail has a variety of terrain through its different sections, including a paved section of trail in the Historic District of West Dover. This paved portion is just over a mile long and is a great way to enjoy an easy walk with a great view.
Hoot, Toot, & Whistle Trail
***The Hoot, Toot, & Whistle Trail will be closing for the season beginning July 14, 2025 for renovation construction. Make sure to check out the rebuilt trail in 2026!***
The Hoot, Toot, & Whistle is a multi-use trail that is named after the railway whose rail bed the trail now follows. This 2 mile trail begins at Reardon’s Bridge in downtown Wilmington and follows the Deerfield River before meandering along the shoreline of Harriman’s Reservoir and finally ending at the reservoir’s picnic & swimming area. A perfect hike with great views before dinner in downtown Wilmington.
Crosstown Trails
The Crosstown Trail system gives hikers access to more than 5 miles of trails with terrain for various abilities. The inter-twining trail system allows you the options to combine trails for a tailored experience just for you. Whether you want a quick 20 minute stroll down the main Crosstown Trail corridor, create a 2 hour long expedition, or something in between this trail system provides.
Mount Snow
When you hike to the top of Mount Snow you are rewarded with magnificent views as far as the eye can see. Explore their 7 different hiking trails, ranging in all lengths and abilities. You can also plan your hike on a day when the Bluebird Express is offering scenic lift rides – hike up, enjoy the views at the Bullwheel restaurant at the summit, and then have the chair lift take your weary legs back down for an all around experience.