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The Yankee Express

Out of the Woods and on the Road: The Midstate Trail in Sutton

Dec 05, 2025 11:43AM ● By Thomas J. McLaughlin

“We have enjoyed doing it all, though naturally some parts are more attractive and scenic than others. There are sections with too much road walking,” George W. Outerbridge wrote in 1939. (Great Stories of the Appalachian Trail)

Outerbridge, a Pennsylvania gynecologist and the second person to complete the Appalachian Trail (AT) in sections, was describing portions of the newly created AT in Massachusetts, New Jersey, and elsewhere in the 1930s.

The father of the AT (it was his idea), Shirley native Benton MacKaye, wanted an uninterrupted, unbroken wilderness trail even if it meant breaking up the trail. It was a big enough issue to him that he had a falling out with Myron Avery over it. Avery, a Maine lawyer worked tirelessly to create the AT. MacKaye was against constructing Skyline Drive and the Shenandoah National Park, while Avery supported it.

Myron Avery was the first to hike the entire trail in sections. He wanted one long trail from Maine to Georgia, even if it meant occasional “road walking.” He believed that Skyline Drive and Shenandoah National Park would complement the trail, not detract from it as MacKaye thought.

Over the years the thousands of AT hikers compelled to complete the trail have borne out Avery’s view. While it’s desirable to have a wilderness trail, it’s not always possible. It’s better for it to be one continuous trail, whether it’s the 2,200-mile AT running through fourteen states, or the 92-mile Midstate Trail running through fourteen towns. Aside from the wilderness, a big part of the appeal of these trails is the distance they cover.

The routes aren’t set in stone. Both trails have dealt with development, have depended on private property access, and have been rerouted since they were created. Hundreds of miles of the AT have been rerouted in several states. Obviously, the 92-mile Midstate reroutes have been smaller.

But when it comes to “road walking” you would be hard pressed to find a nicer walk than on the country farm roads of the Midstate in Sutton.

Two and half miles of the Midstate Trail runs through Sutton with a mile and a half of it on roads—Douglas Road and Town Farm Road.

–Whittier Farms is on the Midstate Trail. The farm is 12 miles into the hike from the southern terminus of the Midstate at the MA/RI border and 80 miles from the northern terminus at the MA/NH border. It’s a five-mile walk on the Midstate from Route 16 in the Douglas Woods.

This “five generations, five hundred acres” farm welcomes Midstate hikers, encouraging you to visit their Farm Store where they sell a variety of deli meats and other foods you can purchase for your hike. They also offer daytime parking. For additional details you can visit their Midstate page on their website:whittiers.com/midstate.

“Most of our land along the Midstate Trail is preserved open agricultural land through the Massachusetts Agricultural Preservation Restriction. Our fields provide picturesque panoramic vistas along the trail even though our area is primarily over-the-road trail,” according to their webpage.

I walked here on a beautiful sunny afternoon in May when the sky was blue and the fields were green. Seeing hundreds of acres of wide open, rolling farmland is a rare sight to behold these days. If you’re not up for the walk to this area you can always drive here.

The leafy tree-lined Town Farm Road off Central Turnpike is also scenic with its stone walls and green pastures. It’s all uphill and it will give you a workout on any day, especially on a hot one. It’s at this point at the top of the hill where the north/south direction of the trail turns west, veers across the field into the forest and heads to Oxford.