Berkshire Trails Worth the Trek: Top Autumn Hikes and Scenic Views
Fall in the Berkshires is magical, with crisp air, vibrant foliage, and trails that wind through some of the region’s most breathtaking scenery. Take your time on these hikes, soak in the colors, and make it a full weekend getaway with a cozy stay at a Red Cottage home. From challenging peaks to peaceful forest paths, these trails showcase the season at its finest.
Bash Bish Falls
📍Falls Rd, Mt Washington, MA
A classic fall destination, Bash Bish Falls delivers a stunning waterfall surrounded by vibrant foliage. This 2.1-mile hike is moderate, with a few inclines that make the view at the bottom even more rewarding. Take your time and enjoy the sound of cascading water as the leaves blaze in autumn colors. Perfect for soaking in scenery without rushing.
The Cobbles Lookout via the Appalachian Trail
📍Furnace Hill Rd, Cheshire, MA
The Cobbles offers sweeping views of the Berkshires and Taconic Mountains. This 1.7-mile moderate hike is short but steep in sections, making it a satisfying climb for a morning adventure. Pause at the lookout to catch the colorful canopy stretching across the hills.
Alander Mountain
📍162 East St, Mt Washington, MA
Alander Mountain’s 5.8-mile moderate trail is ideal for a half-day adventure. The route winds through forests and rocky ridges, rewarding hikers with panoramic vistas at the summit. Enjoy the crisp fall air as you trek this scenic mountain trail.
Mount Race and Race Brook Falls
📍716-732 S Undermountain Rd, Sheffield, MA
Race Brook Falls is a 5.7-mile hike that combines a challenging climb with a stunning payoff. Steep inclines and rocky terrain make it a trail for more experienced hikers, but the cascading waterfalls framed by fall foliage are worth every step. A full morning or afternoon of adventure.
Mount Greylock via Bellows Pipe Trail
📍1200 Notch Rd, North Adams, MA
The highest peak in Massachusetts deserves a hike with a bit of challenge. At 5.9 miles and hard difficulty, this trail climbs steadily to Mount Greylock’s summit, offering sweeping autumn vistas. Take your time and savor a weekend escape with a Red Cottage stay nearby.
Appalachian Trail: Jug End Rd to Mount Bushnell
📍256 Guilder Hollow Rd, Egremont, MA
This 3.6-mile moderate section of the Appalachian Trail is perfect for hikers seeking a manageable trek with rewarding views. Gentle inclines and forested paths make it ideal for a half-day hike in vibrant fall colors.
Monument Mountain via Hickey & Peeskawsa Peak Loop
📍546 Stockbridge Rd, Great Barrington, MA
A 2.4-mile moderate loop packs in striking rock formations and summit views over the Housatonic Valley. The trail has some steep spots but remains very accessible, making it a favorite for quick hikes with dramatic scenery.
Laura’s Tower Trail
📍2 Park St, Stockbridge, MA
Laura’s Tower Trail is a 1.8-mile moderate hike that climbs to a charming stone tower with panoramic views. The trail is perfect for a short morning outing, allowing plenty of time to linger and soak in autumn’s full spectacle.
Olivia’s Overlook and Charcoal Trail
📍Yokun Ridge South, Hiking Trails, West Stockbridge, MA
This 1.7-mile moderate loop is ideal for a leisurely fall hike with colorful forest views and peaceful overlooks. A short, manageable trek that gives a sense of adventure without requiring a full-day commitment.
Umpachene Falls
📍Umpachene Falls Rd, New Marlborough, MA
A tiny gem, Umpachene Falls is only 0.3 miles and easy for all skill levels. This short trail delivers big rewards with cascading water and brilliant fall leaves—a perfect quick stop on a weekend getaway.
Burbank Trail
📍Richmond Mountain Rd, Richmond, MA
A 3-mile moderate hike through wooded terrain, the Burbank Trail offers a peaceful retreat into nature. Gentle inclines make it accessible while still providing satisfying autumn vistas along the route.
Explore the Berkshires this fall and take in stunning views, vibrant foliage, and trails for every skill level. After a day of adventure, rest your feet and make it a weekend getaway at a cozy Red Cottage home nearby.
