Hikes for Every Activity Level:
Beginner/Easy Winter Hikes
Moderate Hikes to Try This Winter
Challenging Winter Hikes
When winter rolls into Massachusetts, the state transforms into a peaceful winter wonderland perfect for outdoor adventures. Frosted trees, snow-covered trails, and crisp air make this the ideal season to bundle up and explore the great outdoors. Whether you’re looking for a scenic stroll, a moderate trek with breathtaking views, or a heart-pumping challenge, there’s a trail for every skill level. Lace up your boots, fill your thermos, and let’s explore the best winter hikes in Massachusetts, all perfect for winter day trips from Boston.
Easy Hiking Choices for All Ages
If you’re new to winter hiking or simply want a relaxing nature walk, Massachusetts offers plenty of easy trails that still deliver on amazing scenery -these trails are a great place to start!
Broadmoor Wildlife Sanctuary – Natick, MA
One of the easiest, and most accessible, places for hiking during the winter is Broadmoor Wildlife Sanctuary in Natick. Offering over 8 miles of trails, including a 0.6 mile Universally Accessible All Persons Trail, this is a great place to bring the whole family for your winter hike. On the All Persons trail, wooden boardwalks wind through frozen wetlands, offering peaceful birdwatching and the chance to see otter tracks in freshly fallen snow. We also recommend the Boundary Trail, where you have a chance to see Great Horned Owls here in the wooded areas during the winter! Check out all the trails at Broadmoor on their website.
Castle Neck Dunes Hike – Ipswich, MA
This is one of the most unique hikes in all of Massachusetts, and each season brings a new hiking experience! The large dune system surrounding Crane Beach has multiple trails, ranging from easy to moderate difficulty. With over 3 miles of paths to explore, you can have a different experience each time. The trails take you through pitch pine forests, alongside almost-frozen marshes, and atop windswept dunes with winter seabirds gliding overhead. Those who want a guided tour through the dunes while learning more about the plants, wildlife, and unique dune ecosystem can sign up for a Guided Hike through the Dunes of Castle Neck with Keolis massAdventures. When you book with Keolis massAdventures your day trip includes seamless round-trip transportation from Boston to Crane Beach using the Commuter Rail and shuttle van, the MBTA Commuter Rail Weekend Pass, and, of course, your ticket on the guided dune hike.
Ravenswood Park – Gloucester, MA
Managed by the Trustees of Reservations, Ravenswood Park has over 10 miles of trails and paths, ready to explore! Some trails like the Ravenswood Park Trail are easy, some – like the Ravenswood Outer Loop – are more moderate. At Ravenswood Park, you can wander through quiet woods, past granite boulders and frozen wetlands. The Ravenswood Outer Loop offers beautiful winter vistas, and you may catch a sight of chickadees or owls. After your hike, head back downtown to warm up with a chowder at one of Gloucester’s cozy seafood spots! Ravenswood Park is about 3 miles from the Gloucester Station, accessible by the Newburyport/Rockport line.
World’s End – Hingham, MA
One of our favorite places for an easy winter hike in Massachusetts is at World’s End in Hingham. Another Trustees of Reservations property, World’s End has over 4 miles of trails, carriage paths and footpaths across its four drumlins. We recommend the World’s End Trail Loop as one of the best choices for beginner hikers, families, or those looking for a more relaxed hike. The gentle hills, coastal views, and a picture-perfect city skyline offer a one-of-a-kind hike.
Moderate Winter Hikes in Massachusetts Accessible by Commuter Rail
If you’re ready to break a sweat while still enjoying manageable trails, Massachusetts has no shortage of moderate winter hikes with stunning views and rewarding climbs.
Blue Hills Reservation – Milton, MA
Just minutes from downtown Boston, Blue Hills Reservation transforms into an actual winter wonderland, full of wooded trails and open ridges. The Skyline Loop, a 5-mile looping trail, offers incredible panoramas of the city skyline and is home to deer, foxes, and red-tailed hawks. The trails here vary in difficulty, but are more moderate during the winter with snow and icy on the trails. Blue Hills Reservation is just a few miles from the MBTA Commuter Rail Readville Station. To get there you can take the Fairmont line to Readville, then walk or use a rideshare service to get to the Blue Hills Reservation.
Bradley Palmer State Park – Topsfield, MA
For a mix of forest and history, head to Bradley Palmer State Park in Topsfield. This grand-estate-turned-state-park was home to prominent attorney Bradley Palmer in the early 20th century. Upon Palmer’s passing, the estate was donated to the state of Massachusetts to be turned into a state park. Today, the 721 acres feature meadows and trails perfect for hiking, biking, and even cross-country skiing! Explore the Bay Circuit Trail, Moon Hill, a 5.2-mile loop with some moderate ascents and descents that can become more challenging in snow or icy conditions. You’ll meander through pine groves and across frozen brooks, making this hike seem like it’s straight out of a storybook. Bradley Palmer State Park is about 4 miles from the Hamilton/Wenham Station, accessible by the Newburyport/Rockport Commuter Rail line.
Wachusett Mountain – Princeton, MA
Head further west for a true alpine feel without leaving Massachusetts at Wachusett Mountain State Reservation . The Mountain House Trail to Balance Rock Loop stretches just over 4 miles, offering snowy forest paths, icy rock formations, and sweeping summit views that make the climb worth every step. Don’t forget your camera – this area is known for bald eagle sightings near the Wachusett Reservoir. The trails here are well-marked and make for a true New England winter adventure! Wachusett Mountain State Reservation is 5.6 miles from the Wachusett Station on the Fitchburg line.
Mount Misery – Lincoln, MA
For a peaceful hike, head to Mount Misery in Lincoln for the Mount Misery loop. It winds four miles through meadows, forests and riverside paths along the Sudbury River. Despite its gloomy name, this trail is anything but dreary – especially when blanketed in snow! It’s also one of the most accessible winter hikes from Boston, just a short 1.7-mile walk from the Lincoln Station on the Fitchburg line.
Massachusetts’ Most Challenging Winter Hikes
Mount Greylock – Adams, MA
Kick off your challenging winter hikes in the Berkshires at the tallest peak in Massachusetts, Mount Greylock. The Cheshire Harbor Trail to Mount Greylock is a 6.5-mile round-trip route that winds steadily through quiet forests before emerging at a summit that feels like another world. The views stretch across snow-covered valleys, and on clear days you can see as far as 90 miles, to New Hampshire, New York, and even Vermont! The trails here are prime territory for spotting porcupines and bobcats, especially in the early mornings. Parts of the trail are rocky, and can be extra slippery with rain, snow, or icy conditions.
Mount Tom State Reservation – Holyoke, MA
The best spot in Massachusetts – and arguably all of New England – to see hawks is Mount Tom Reservation. Offering multiple trails to traverse, but we like the MA Net: Section 6 for a nice, challenging winter hike. Section 6 includes epic overlooks, diverse terrain, and of course multiple spots to see hawks soaring overhead. It also offers a view of the spot that inspired artist Thomas Cole to create ‘The Oxbow’ painting in 1836.
Mount Watatic – Ashburnham, MA
Grab your hiking boots and microspikes for a climb up to the summit of Mount Watatic. A visit to this old ski area allows you to access many different trails, with varying levels of difficulty. We recommend the Mount Watatic & Nutting Hill loop. This 3-mile loop brings you first to the summit of Mt. Watatic, then showcases sweeping views of Boston and Mt. Wachusett. Be mindful of the trail markers – there are many trails that intersect this one along the Wapack Trail, and if you take a wrong turn you could end up hiking into New Hampshire! For those up to the challenge, the Wapack Trail hike into New Hampshire can be a multi-day hike, please research further before setting out.
Mount Holyoke Range State Park – Amherst, MA
Difficulty: Hard to Expert level!
Best for seasoned hikers, the Mount Holyoke Range State Park in Amherst offers rugged terrain and incredible views of the valley below. The Seven Sisters via New England Trail is a 4-mile one-way, or 8-mile round-trip hike and is considered one of the best in the state. This trail offers steep ascents and descents along a forested ridgeline, perfect for those looking to test their endurance on a cool winter day. As with all hikes, we recommend mapping out your route ahead of time.
Tips for Safe and Enjoyable Winter Hiking
Winter hiking can be magical, but preparation is key! Before heading out, always check the weather and trail conditions, and pack essentials. The American Hiking Society has a list of 10 essentials if you need somewhere to start. Essentials include: appropriate footwear, a first aid kit, food, water and water purification (iodine drops, chlorine tablets), safety items (headlamp or flashlight, fire starter, and a whistle), map and compass/GPS, knife or multi tool, sun protection, shelter, and layers. Always dress in fast-drying layers made of wool or moisture-wicking fabrics, and bring rain gear, to stay warm and dry. Footwear should have good traction and support, and for icier conditions bring micro spikes. Start early since winter days are short – and let someone know your plans! Finally, we recommend packing trekking poles. In addition to helping with balance and support, they’re also a useful tool for checking water or snow depth.
Car-Free Winter Hiking Adventures with Keolis massAdventures
If you want to skip the winter driving, Keolis massAdventures makes getting outside for a winter hike easier than ever! Sign up for the Dunes Hike at Castle Neck Beach on the Crane Estate in Ipswich, a perfect car-free winter day trip from Boston. You’ll enjoy a guided tour through windswept dunes, frosted marshes, and scenic coastal landscapes, all while learning about the local wildlife and ecology. Your adventure includes round-trip transportation on the MBTA Commuter Rail, a private shuttle to the beach, and your guided hike ticket – all you need to do is show up and enjoy the day!
Embrace the Chill and Get Outside
Winter hiking in Massachusetts is more than just exercise, it’s about embracing the quiet beauty of nature when the world slows down. Whether you’re wandering through snow-covered forests, scaling frozen ridges, or exploring scenic coastal trails, each step offers peace, perspective, and adventure.
So lace up your hiking boots, breathe in that crisp New England winter air, and discover the magic of winter hikes in Massachusetts, one snowy trail at a time.
