6 Stunning Fall Hikes in Southern New England 

The leaves may already be falling in much of New Hampshire, Maine, and Vermont, but that doesn’t mean leaf-peeping season is over. Southern New England — Massachusetts, Connecticut, and Rhode Island— offers dense forests, idyllic landscapes, and later peak foliage.  

Here are a few of our favorite trails to enjoy on a crisp fall morning, with trail descriptions from AMC’s collection of hiking guides. Enjoy abridged sneak peeks from Best Day Hikes in Connecticut and Rhode Island and Best Day Hikes: Central Massachusetts, 2nd Edition, both available to purchase in Spring 2024.   

Stony Ledge Via Haley Farm Trail (5.6-Mile Loop) 

Williamstown, Massachusetts 

From AMC’s Best Day Hikes in the Berkshires, 3rd Edition: 

This short but fairly steep hike in Mount Greylock State Reservation leads to one of the most scenic panoramas in the entire commonwealth. The return is by way of one of the reservation’s most popular trails along the southern slope of the bowl-shaped Hopper. 

Walk past the barn and a farm gate bordered on both sides by hayfields and then around a state forest gate. Continue along an old cobbled lane under a canopy of sugar maples for a couple hundred yards to the signed Haley Farm Trail intersection, where there’s a fine easterly view to the Hopper. Turn right and follow blue-blazed Haley Farm Trail through a hayfield and up into the forest. The path, initially level as it passes through the shade of maple, birch, and white ash, steepens before bearing left on the first of a series of four major switchbacks that take you up the slope. 

Keystone Arches Trail 

Middlefield and Chester, Massachusetts 

From AMC’s Best Day Hikes in Central Massachusetts, 2nd Edition: 

This out-and-back trail offers a combination of history and backcountry scenery, including the distinctive Keystone Arches bridges, views of the West Branch of Westfield River, and tumbling streams. 

During the 1840s, the Western Railroad chose the remote, rugged valley of the West Branch of Westfield River as the site of America’s first mountain railway. In spite of the many engineering challenges presented by the steep, rocky terrain, the valley offered the most feasible route across the Berkshire Hills to the crucial markets of New York State and beyond. The construction of the rail line, which was designed by George Washington Whistler, included a series of giant stone arch bridges known as the Keystone Arches. The czar of Russia subsequently commissioned Whistler to build the Trans-Siberian Railroad. 

Keystone Arches Trail, established by the Friends of the Keystone Arches (an organization committed to the preservation of these unique structures), parallels Westfield River and crosses two abandoned bridges that were designated as National Historic Landmarks in 2021. Most of the route passes through Walnut Hill Wildlife Management Area, which is owned by the Massachusetts Division of Fisheries and Wildlife. The trail is marked with blue blazes and trail signs; several interpretive signs provide information about the historic railroad and the watershed. Seasonal attractions include cascading streams, wildflowers, and migratory songbirds in spring and colorful foliage in fall. 

 

Want to experience the best of Western Massachusetts? Visit the AMC Noble View Outdoor Center 

 

Middlesex Fells Reservation 

Malden, Medford, Melrose, Stoneham, and Winchester, Massachusetts 

From Massachusetts Trail Guide, 11th Edition: 

Established as a public reservation in 1894, Middlesex Fells (fell is a Saxon word meaning “rocky place”) consists of 2,575 acres in Stoneham, Medford, Winchester, Melrose, and Malden, just a few miles from downtown Boston. The diverse habitats include rugged low hills, mixed forests, ponds, brooks, reservoirs, and granite outcroppings traversed by fire roads, bridle paths, and footpaths. Many overlooks afford fine views of the surrounding area, including Boojum Rock, White Rock, and the stone observation towers on Pine Hill and Bear Hill, as well as nearby Boston. Because of its proximity to the city, Middlesex Fells is a very popular destination. 

A map of the reservation is available at the DCR [Department of Conservation & Recreation] website. Additional resources are available from the Friends of the Middlesex Fells Reservation 

Talcott Mountain (2.5-mile Loop) 

Avon and Simsbury, Connecticut 

From AMC’s Best Day Hikes in Connecticut and Rhode Island: 

This is one of the most popular places to walk and enjoy nature in central Connecticut. On weekends and at other peak times, Tower Trail gives plenty of opportunity to chat with fellow hikers. The Heublein Tower, featuring fantastic views, makes this loop hike worthwhile anytime. 

Tower Trail begins on the left side of the access road, about 1,000 feet from the CT 185 entrance, but a less crowded, unmarked feeder path begins farther uphill at the Life Star helicopter pad. 

From the far end of the helicopter pad, this unnamed trail enters woodland and proceeds south amid black birch, oak, maple, and hickory. Mountain laurel and clumps of witch hazel are the understory plants, along with tufts of Christmas fern. The path is wide and easy to follow as it begins to gently traverse the rocky hillside. The grade steepens as the woods change to waves of evergreen hemlock alternating with oak, maple, birch, and other hardwoods. The path splits into several strands, but they all lead in the correct direction. 

Mount Tom State Park (1.25-mile Loop) 

Washington, Connecticut 

From AMC’s Best Day Hikes in Connecticut and Rhode Island: 

A loop hike at this state park is a wonderful outing for families with children, featuring panoramic views from a medieval-looking stone tower perched atop an easy-to-reach summit. 

If you seek lofty views for minimal effort, this short trip is for you. At 232 acres, Mount Tom State Park—one of Connecticut’s oldest—has plenty to offer. The hike is an excellent way to introduce young children to the joys of summiting. The climb is mostly gradual, with one short, steep stretch on the descent. Moderately deep and clear, springfed Mount Tom Pond is a great place to cool off after your trek. 

From the gravel parking area, walk the wide pathway a short distance to a fork; follow the right path by a wooden barway. Yellow blazes mark the Tower Trail as it bears left over a rough gravel roadbed through an oak-dominated woodland. Bear right at the split. Look down as you tread over a shiny gneiss outcropping, polished by mile-thick ice some 25,000 years ago. 

Ell Pond and Long Pond (5.3-mile Loop) 

Hopkinton, Rhode Island 

From AMC’s Best Day Hikes in Connecticut and Rhode Island: 

The rocky trail south of the parking area requires hikers to scramble almost immediately over jumbled boulders while entering a lush corridor of Rhododendron maximum, also known as great laurel.  

This enormous evergreen shrub—more like a small tree, reaching 20-plus-feet tall— is a wild variety of the cultivated rhododendron planted in suburban neighborhoods and city parks. With leathery, 8-inch leaves and thick, gnarly trunks, Rhododendron maximum dominates the understory in a hemlock forest. 

In any season, the verdant canopy is a glorious introduction to this yellow-blazed section of the Narragansett Trail. In Connecticut, the 20-plus-mile footpath is marked by blue blazes. Wooden steps up a steep slab not far from the trailhead help make the climb easier; the trail crests near the intersection of two unmarked but clearly defined paths in 0.2 mile. 

 

Find new trails to explore across New England and the Mid-Atlantic with AMC’s Hiking Guides.