11 great places for trail running in the fall and winter

Trail running presents a paradox: you run slower yet the time goes faster; you work hard but finish feeling refreshed.

The restorative nature of trail running has something to do with the fact that it demands your undivided attention, thanks to the varied terrain and steeper grades, the rocks and roots, and the constantly changing scenery. And there’s the power of nature itself—clean air tinged with the tang of salt or the spice of the pines, the sound of birds chirping and the wind flowing through the trees, glimpses of wildlife just beyond the edge of the trail, and the endless gradations of color, be it green, blue, gray or brown.

Two men running on a trail next to a fieldTrail running gets better as the year grows old. The cooler weather that comes with fall and early winter makes running more comfortable. Ticks, mosquitos and other insects are mostly gone. And as the trees shed their leaves, new vistas open up in the woodlands, allowing you to see further into your surroundings.

Of course, autumn also heralds the start of hunting season so it’s important to take proper precautions, such as wearing blaze orange and other brightly colored clothes, avoiding areas where there are sights and sounds that indicate the presence of hunters, and avoiding early morning and late day runs when hunters and animals are most likely to be active. Pro tip: hunting is not allowed on Sundays, so that’s a great time to plan a trail run. (For more, the Trail Sisters website offers some excellent tips.)

The Buzzards Bay watershed region boasts so many great places for trail running that it can be hard to know where to start. You can find them by the dozens on Discover Buzzards Bay.

The list below, organized from west to east, contains some of our favorite spots—both places that are well known to dedicated trail runners as well as some hidden gems. If your favorite didn’t make the list, let us know about it.

But most of all, get out there for a run or a jog.  No matter where you choose to ramble, you’re sure to find space for exercise, relaxation and–yes–serenity.

1. Simmons Mill Pond Management Area (Little Compton)

Simmons Mill Pond Management Area offers an inviting spot for a run, with its seven ponds, hand-lettered signs and pleasant trails. The paths here are primarily grassy old cart tracks that make for good footing and easy running. The trail network features two main loops that are connected and add up to roughly three miles. And the woodlands, a coastal maritime oak-holly forest, are a rare habitat that only grows in the right conditions in southern New England. This unusual forest is home to a rather unusual mammal: the Southern flying squirrel, a fascinating little mammal that glides from tree to tree on the skin between its wrists and ankles. Flying squirrels are nocturnal, but you may see one if you are finishing your run near dusk.

2. Westport Woods Conservation Park (Westport)

For nearly fifty years, when it was the St. Vincent de Paul camp, kids of all backgrounds called this property on the border of Westport and Adamsville their summer home. It’s still a great place to play. The woods here hold almost three miles of trails, which begin directly off the parking lot in the front fields. The paths are mostly flat, running from meadows through woodlands and wetland areas, with side trips to a former quarry that is now a peaceful pond. There is a small island on the pond’s southern end that you can venture out to when water levels are low and pause for a great view of the surrounding waters.

3. Destruction Brook Woods (Dartmouth)

Bay Adventure Run at Destruction Brook Woods

The 10-mile network of well-maintained trails at Destruction Brook Woods will allow you to get in a fairly long run, if that’s your goal. You can easily organize a short jog here, too, by sticking to one of the shorter loops. Either way, what’s particularly nice about this location is the variety—from wide and flat paths through open woodlands to narrow and steep single-track-style trails that plunge through hilly upland forests and Happy Valley.

4. Watuppa Reservation (Fall River)

For the serenity of the deep forest, the Watuppa Reservation managed by the City of Fall River is hard to beat. Part of the massive Southeastern Massachusetts BioReserve, the reservation contains miles of trails—from grassy roadways to narrow, winding tracks. The wide and well-maintained Brightman Path invites you to coast over rolling hills and offers the option to return via the Corduroy Path, which–be warned–earned its name from the tree roots that criss-cross this trail through a fascinating wetlands area. Or for a longer run, you can continue on to a network of lovely single-track trails and cart paths at Copicut Woods, a property maintained by The Trustees.

5. Freetown-Fall River State Forest (Freetown)

This is a place that offers both the opportunity for rugged adventure as well as a fairly gentle introduction to trail running. The 5,441-acre state forest is criss-crossed by trails of all types and for all purposes. To start, the park contains several wide and open dirt roads that could easily form a very accessible trail run, everything from a short out-and-back jog on Payne Road to a much longer loop with a paved section along the lightly-traveled High Street on the western edge of the forest. The park also contains narrower paths, such as the Massasoit Trail, that will immerse you in deep woods.

6. Betty’s Neck (Lakeville)

This is a picturesque park that offers great variety over its three-plus miles of trails. The heart of Betty’s Neck are the grassy paths that outline the margins of two large meadows on the site. Those two loops, which are connected, add up to roughly 1.5 miles for a nice jog or a large track for multiple circuits. You can also head off into the woods on narrower trails, with a few steep hills, that lead to the edge of Assawompset Pond. Finally, if you really want miles (or want to avoid driving over deeply pot-holed dirt roads) you can park at the entrance to the cranberry bogs and run up to Betty’s Neck, which would probably add two more miles to your run out and back.

7. The Bogs (Mattapoisett)

Start out on the sandy, level paths of a former cranberry bog and work your way toward lush woodlands and wetlands with trails that connect to the nearby Tinkhamtown Woodlands, Tripps Mill and the New Boston Trail. There’s a lot of variety here, from birdsong-filled beech groves to vernal pools croaking with frogs to vibrant cranberry bogs and rare freshwater swamps. With so many trail options, you can do everything from a casual one-mile jog to an epic six-mile-plus, expedition-style run.

8. Aucoot Woods: White Eagle Parcel (Marion)

From forest to bog, the White Eagle Parcel of Aucoot Woods is a beautiful place for trail runners to explore. As such, don’t be surprised if you find yourself constantly waving to other runners along your journey! Whether you find yourself on the larger, muddy red and white trails or the more serene bog trails, this Sippican Lands Trust property is a great place to run, especially at golden hour just before sunset.

9. East Over Reservation (Rochester)

East Over Reservation offers pastoral atmosphere for your run on the margins of broad, open fields; lanes lined with mature trees; and elegant stone walls. The property, which is managed by The Trustees, was once part of a larger farm that’s still in operation today. From the parking area on Clapp Road,you will find easy and scenic running on the trails that outline the property. If you don’t mind a short section of pavement, you can create a large loop by linking the trails that exit the property at Hiller Road.

10. Myles Standish State Forest (Carver)

The 12,000-acre Myles Standish State Forest is the largest recreation area in southeastern Massachusetts, with 13 miles of hiking trails and ponds galore. The forest offers dozens of potential options for short runs and long-distance trips alike. You can even camp here or take a swim after your run to fully explore all this great location has to offer!

11. Beebe Woods (Falmouth)

There are at least a dozen possible running adventures in Beebe Wood’s extensive network of old carriage roads and foot paths. First, you must choose from parking areas on the main compass points of the property—Ter Heun Drive (north), Highfield Hall (east); Sippewissett Road (west) and at neighboring Peterson Farm (east). And then, you will have nearly seven miles of trails to explore, traveling over the rocky remnants of the area’s glacial past and through diverse woodlands filled with oaks and pines, as well as beech, tupelo, Atlantic white cedar, sassafras, and hickory.

Category: Featured Adventures

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