5 Family Friendly Winter Hikes in Central Mass


I don’t know about you, but this is the year that I am determined to become a winter person. Checking out different hiking spots with my dog was one of my very favorite activities pre-kids. But somehow, galavanting through the woods lost a bit of its appeal after a hike or two with a small child crying in a carrier 20 minutes into our 2-hour hike.

Now that my older two kids can hike about 2 miles on their own, and their baby brother doesn’t share their disdain for the baby carrier, we are in a great routine of hiking regularly 2-4 times per week. While we’re in the woods I feel like I can breathe a bit easier. Like the weight of the world fades into the background for at least an hour or two.

I can’t lose that connection to nature, or to myself.

Here are some of the family friendly hiking spots we are planning on frequenting this winter. Bundle up, and perhaps we’ll see you on the trails.

Mt. Pisgah – Berlin, MA

Mt. Pisgah has a variety of trails and loops and a really beautiful overlook at the end of our favorite trail. We like to follow the blue blazes to the outlook and then turn around to head back to the parking lot which turns out to be a little less than 2 miles. Although there are a decent amount of rocks and tree roots there is a gentle elevation climb and the trails are easy even for my 3-year-old. To access the trails it’s easiest to type in 24 Smith Road, Northborough into your GPS.

Hopkinton State Park – Hopkinton, MA

Hopkinton State Park is one of our favorite winter spots. What is so nice about it is that in the winter they gate off all of the interior roads, but still plow them. This way you have the option to check out a trail in the woods or take a stroller with you and just walk on the roads! There is plenty of parking and lots of trail options to explore with gentle trails.

Moore State Park – Paxton, MA

Moore State Park can be crowded, but it’s a beautiful spot nestled right in central MA. There is a variety of terrain and scenery including a bridge and dam, open fields, ponds, rocks, and old buildings. With plenty of parking and easy trails for little ones, Moore State is a great option if you don’t want to venture too far from home.

Chestnut Hill Farm – Southborough, MA

I am having a full-on love affair with the Trustees properties right now. The Trustees managed properties are always so well marked, with lots of information available on their websites. Chestnut Hill Farm is a working farm and one of the lovely Trustees properties. There are quite a few trails with the option to add on to smaller loops. Because this is a working farm you sometimes get to see sheep and other animals, but dogs are not allowed. It’s also important to stay on the trails and away from the fences that may be electrified. As an added bonus this property has a farm stand that you can order from online, and they’ll bring your order right out to your car! A hike and fresh local groceries?! Yes, please.

Rockhouse Reservation – West Brookfield, MA

Full Disclosure, we haven’t been here yet. BUT it’s a Trustees property so I already know we’ve going to love it. Just west of Worcester, Rockhouse Reservation gives you a glimpse into the ice age with monumental boulder formations and cave-like structures to check out along the trails. We can’t wait to check out this spot and I know my kiddos will LOVE exploring the “rock house” near the pond.

What are your go-to outdoor activities in the winter?

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Kara is a Perinatal Fitness Specialist and Pregnancy and Postpartum Athleticism Coach.  A momma of two amazing littles, lover of the beach, former college athlete who has never met a pizza she didn’t like. She lives in Central Massachusetts with her husband, 2 kids, 2 crazy dogs, 5 chickens, and a beta fish named Nemo 2.0. Through her online and one on one coaching, Kara helps women find joy in motherhood through movement using rehabilitative and corrective exercise strategies. She is on a mission to dispel myths that leave women fearful of movement and empower women with knowledge and confidence to help them better navigate their new role as a mother. Kara thinks all problems can be solved with either a chocolate chip cookie or the ocean, and loves checking out local small shops and breweries. Her favorite type of movement right now is hiking with her dogs and is grateful to be surrounded by so much natural beauty here in New England. 


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