Things to do in Cheshire
Cheshire, Massachusetts, is a small town where outdoor activity is the main draw.
Neighborhoods
Cheshire, Massachusetts, is a small town where outdoor activity is the main draw. With just two standout spots, it’s a quiet place for a bike ride, a walk, or picking up garden supplies. The Ashuwillticook Rail Trail runs through town, and Whitney’s Farm Market & Garden Center adds a local stop for plants and seasonal produce.
The Ashuwillticook Rail Trail is the town’s anchor for recreation—a flat, family-friendly path on an old rail line, open to walkers and bikers, with cross-country skiing in winter. It’s also dog-friendly, making it an easy outdoor option for visitors. For a slower pace, Whitney’s Farm Market & Garden Center sells plants, flowers, vegetables, breads, and seasonal pies. Cheshire doesn’t have much else in the way of commercial attractions, but for those who want a simple outdoor day, these two places cover it well.
Frequently asked questions about Cheshire
What outdoor activities are available in Cheshire, MA?▾
The main outdoor activity is using the Ashuwillticook Rail Trail, which is good for biking, walking, and cross-country skiing in winter. It’s a flat, old train route, so it’s easy for families and dogs. Otherwise, you can visit Whitney’s Farm Market & Garden Center for garden supplies and fresh produce, though that’s more of a stop than an activity.
Is the Ashuwillticook Rail Trail good for kids?▾
Yes, the trail is good for children. It’s a paved, relatively flat path along a former rail line, so it’s suitable for young bikers or walkers. Dogs are also allowed, which makes it a convenient spot for a family outing. Just bring water and sunscreen, as there’s limited shade in some sections.
What can I buy at Whitney's Farm Market & Garden Center?▾
Whitney’s sells a range of plants, flowers, and garden supplies, plus vegetables, breads, and seasonal pies. It’s a typical farm market with a nursery attached, so you can pick up both garden items and fresh food in one stop. Seasonal pies are a highlight, though availability varies by time of year.
Is there cross-country skiing in Cheshire?▾
Yes, the Ashuwillticook Rail Trail is used for cross-country skiing in winter. Because it’s a flat, old rail bed, it provides an easy skiing surface when there’s enough snow. There are no rental shops in town, so you’ll need to bring your own gear.
Are dogs allowed on the Ashuwillticook Rail Trail?▾
Yes, the trail is dog-friendly. You can walk or bike with your dog on the path. The trail is flat and open, which makes it a good option for a straightforward dog walk. Just keep your dog leashed and clean up after them, as is standard on shared-use trails.
