Brookline VermontHIKING TRAILS & PLACES TO HIKE


Listed below are the best hiking trails and places to hike near Brookline, Vermont.



1. Mount Watatic Loop via Wapack Trail

SCENIC MOUNTAIN SUMMIT PATH


Mount Watatic Loop via Wapack Trail offers hikers a circular route with stunning panoramic views at the summit. The moderate difficulty trail features diverse terrain through woodland areas and rocky outcroppings that challenge hikers while remaining accessible. Hikers can expect beautiful seasonal foliage and abundant wildlife viewing opportunities throughout the journey.


2. Gile State Forest Loop

TRANQUIL FOREST EXPERIENCE


Gile State Forest Loop combines the Barlow Trail and Winslow Trail to create a comprehensive forest hiking experience. The trail is rated as moderate difficulty with gentle elevation changes and well-maintained paths suitable for most skill levels. Hikers will enjoy dense woodland scenery, seasonal wildflowers, and peaceful stream crossings throughout the loop.


3. Bucklin Trail

CHALLENGING WILDERNESS ADVENTURE


Bucklin Trail provides a challenging hiking experience through pristine Vermont wilderness. The trail features significant elevation gain and technical sections that make it suitable for experienced hikers looking for a rewarding adventure. Highlights include old-growth forest sections, natural rock formations, and impressive vistas of the surrounding Green Mountains.


4. Beauregard Lot via Half Way House

HISTORIC NATURE WALK


Beauregard Lot via Half Way House trail combines natural beauty with historical significance in the Brookline area. The moderate difficulty trail passes by the site of the historic Half Way House, providing cultural interest alongside natural attractions. Hikers will appreciate the well-preserved forest ecosystem, diverse plant life, and occasional wildlife sightings along the route.


5. Windmill Hill Ridgeline Trail

STUNNING RIDGE TRAVERSE


The Windmill Hill Ridgeline Trail spans 16 miles across an undulating procession of small peaks in southeast Vermont including Putney Mountain and The Pinnacle. This challenging trail system offers hikers breathtaking views from multiple vantage points along the ridge that separates Putney and Brookline. Visitors can experience diverse ecosystems ranging from dense hemlock forests to savannah-like woodland areas and open summit ledges.



6. Radford-Smith Trail

SCENIC BROOK CROSSING PATH


Radford-Smith Trail begins at 1200 Grassy Brook Road in Brookline with an immediate dip into dark hemlock woods and a sturdy wood-and-iron bridge crossing over Grassy Brook. The trail climbs steeply through well-graded switchbacks for about half a mile before reaching a distinctive stone wall and large old tree with spread limbs. After the initial climb, the path levels off as it traverses northward across the slope for another half mile to reach the junction with the Cascade Trail.


7. Cascade Trail

FOREST ASCENT ROUTE


The Cascade Trail meanders for 0.8 miles upward to the crest of Windmill Hill Ridgeline from its junction with the Radford-Smith Trail. Along the way, hikers pass through an impressive stand of large oak and ash trees that showcase Vermont's diverse forest ecosystems. The trail ultimately connects with the main Ridgeline Trail, providing access to The Pinnacle's open summit ledge with its remarkable panoramic views.


8. Putney Mountain Summit Trail

POPULAR PEAK HIKE


The Putney Mountain Summit Trail takes visitors along a north-south running ridgeline to reach the 1,667-foot summit of Putney Mountain. This popular hiking destination offers exceptional views of the surrounding Vermont landscape, particularly stunning during fall foliage season. Hikers should note that this trail can become quite crowded during peak seasons due to its accessibility and scenic rewards.


9. Mount Mansfield State Forest Trails

HIGHEST PEAK CHALLENGE


Mount Mansfield State Forest Trails provide access to Vermont's highest peak through Underhill State Park. The trails wind through lush forests and rocky ridges, offering increasingly spectacular views as hikers ascend the mountain. Despite the challenging terrain, the well-maintained path system accommodates various skill levels with multiple route options to reach the summit.


10. Windmill Ridge Nature Reserve

PROTECTED WILDERNESS EXPERIENCE


Windmill Ridge Nature Reserve offers multiple access points including the Grassy Brook Trailhead in Brookline and the Radford Smith Trailhead on Grassy Brook Road. The reserve features a network of interconnected trails through protected wilderness that showcases Vermont's natural beauty and biodiversity. Hikers can customize their experience from short day hikes to longer ridge traverses depending on their starting point and desired difficulty level.