Winthrop MaineHIKING TRAILS & PLACES TO HIKE


Listed below are the best hiking trails and places to hike near Winthrop, Maine.



1. Mount Pisgah Conservation Area

SCENIC SUMMIT AND FIRE TOWER


Mount Pisgah Conservation Area offers moderate hiking with a network of trails totaling approximately 4.4 miles through forested terrain. Hikers are rewarded at the summit with panoramic 360-degree views from a historic fire tower, one of the highest vantage points in the area. The trails are well-maintained and provide a peaceful natural escape close to downtown Winthrop.


2. Roger Guerette Community Trail

ACCESSIBLE FORESTED LOOP


The Roger Guerette Community Trail is a beloved 1-mile loop that winds gently through woods and wetlands behind Winthrop High School. With wide, level paths and educational nature signage, it is accessible for walkers of all abilities, including those with wheelchairs. A spur trail along Hoyt Brook provides a peaceful diversion through diverse habitats.


3. Weston Woods Preserve

LAKE VIEWS AND MATURE FOREST


Weston Woods Preserve features about 1.5 miles of interconnected trails traversing 55 acres of mature forests in East Winthrop. Hikers can enjoy reedy shores of Little Cobbosseecontee Lake and a variety of natural habitats, including the serene Bedrock Spur. The preserve is popular for hiking, nature observation, and peaceful lakeside strolls.


4. Kennebec River Rail Trail

RIVERSIDE RAIL-TO-TRAIL PATH


The Kennebec River Rail Trail stretches more than six miles along the Kennebec River, linking Augusta, Hallowell, Farmingdale, and Gardiner. This flat, paved trail is perfect for walking, jogging, and biking, offering steady river views and access to historic downtowns. Its wide, smooth surface and scenic setting make it a favorite destination for all ages.


5. Whistle Stop Rail-Trail

MULTI-USE SCENIC CORRIDOR


The Whistle Stop Rail-Trail is a 14-mile gravel path stretching from Farmington to Jay, suitable for hiking, biking, and winter activities. Passing through woodlands, wetlands, and rural communities, the trail offers a peaceful backdrop for outdoor recreation. Users appreciate the gentle grades and well-kept surfaces along this multi-use corridor.



6. Eastern Promenade Trail

WATERFRONT URBAN TRAIL


The Eastern Promenade Trail runs for about 2 miles along Portland's waterfront, providing sweeping views of Casco Bay and the city skyline. The trail's paved surface is ideal for walkers, runners, and cyclists seeking an urban escape with maritime scenery. Picnic spots, parks, and historical markers make it a vibrant place to relax and explore.


7. Viles Arboretum

BOTANICAL TRAILS AND GARDENS


Viles Arboretum features over six miles of easy walking trails weaving through diverse gardens, woodlands, and meadows on more than 220 acres. Visitors can explore themed plant collections, wildlife viewing areas, and open fields in a tranquil setting. Educational signage enhances the experience for hikers and families interested in botany and conservation.


8. Cobbossee Stream Trail

STREAMSIDE NATURE WALK


The Cobbossee Stream Trail offers a scenic walk along the banks of Cobbossee Stream, with paths that meander through wetlands and woodlands. Birdwatchers frequent the trail for its abundant wildlife and tranquil environment. Its relatively short, easy loop makes it popular for families and those seeking a brief outdoor retreat.


9. Farrington Mountain Trail

FOREST SUMMIT VIEWS


Farrington Mountain Trail leads hikers through mixed forest to a modest summit with rewarding local views. The single-track footpath is less crowded than other regional hikes, offering solitude and quiet nature immersion. Its moderate incline and manageable distance make it suitable for most hikers.


10. Hallowell Reservoir Trail

RESERVOIR LOOP AND WILDLIFE


The Hallowell Reservoir Trail forms an easy, family-friendly loop around a scenic reservoir just outside downtown Hallowell. The area is well-known for birdwatching and wildlife sightings throughout the year. Shaded by tall trees, the trail is peaceful and accessible for hikers of all ages and abilities.