Great Winter Hikes Near Boston

Great Winter Hikes Near Boston

Are you tired of sitting indoors? Even winter has sunny, beautiful days so there is no reason to stay stuck inside for months. Bundle up, grab a mask, and head out to some great winter hikes near Boston!

1. Blue Hills Reservation

This area is mere minutes from Boston and extends from Quincy to Dedham. This 7,000 acre reservation has some stunning scenery and views of Boston from the top of the Skyline Trail during all seasons. I highly recommend this area to get outside and enjoy nature.

It is important to mention that depending on the trail you choose, some of the paths can be quite rocky. I would naturally recommend proper footwear. If you have some mobility issues, perhaps trekking poles or a walking stick wouldn’t be a bad idea either. A bit unnecessary but it doesn’t hurt to be prepared depending on your personal comfort level.

Thankfully there are several great trails you can take that are indeed suitable for the winter season in terms of length and experience level without sacrificing beautiful scenery.

Be sure to download a copy of the trail map before your visit. Otherwise, All Trails is another great resource for trail guides and further in depth information. They even have a user friendly app you can download. (iOS / Android)

Recommended Trails:

• Houghton’s Pond Recreation Area – Easy – 1.1 mi – 27 min
• Great Blue Hill via Coon Hollow Path – Easy – 1.5 mi – 51 min
• Skyline and Pipe Loop – Easy – 1.8 mi – 53 min
• Elliot Tower via Skyline Trail – Easy – 1.5 mi – 1 hr 2 min
• Wolcott Hill Loop Trail – Easy – 2.3 mi – 1 hr 14 min

2. World’s End Reservation

This is a very easy area to enjoy a nice winter hike in Hingham, MA. It it is a Trustees property so there is a fee to enter the reservation. It is $8 per person for non members and $6 for members. However, children are able to get in for free. This area is fantastic for the scenic bay and ocean views, well maintained walking paths, and the fantastic view of Boston from the top of hill. Their trail map offers some nice mini destinations for your hike or you can do the entire 3.8 mi trail.

Recommended Trails:

• World’s End Trail – 3.8 mi – easy – 1 hr 43 min

3. Middlesex Fells Reservation

This reservation has 2,575 acres of land to explore that extends from Malden, Medford, Melrose, Stoneham, and Winchester, MA. The trail map shows all the numerous trails you can choose from. I prefer the ones that loop around the gorgeous reservoirs in the area. There are so many stunning views to enjoy. The paths were very well maintained as well which is always a bonus in my book.

Recommended Trails:

• Pine Hill – 0.9 mi – easy – 28 min
• Crystal Springs and Whip Hill Road Loop – 1.8 mi – easy – 52 min
• Middlesex Fells Reservoir Loop – 4.1 mi – easy – 1 hr 51 min
• South Reservoir Loop via Sheepfold Trailhead – 4.1 mi – easy – 1 hr 57 min
• West Middlesex Fells Reservation Trail – 5.6 mi – easy – 2 hr 36 min

4. Walden Pond State Reservation

Yes indeed, that Walden Pond. Henry David Thoreau’s classic Walden was inspired from this area in Concord, MA. The trail map shows the three main trails in the area. This reservation is perfect for winter because most of the hikes revolve around the pond. If you have pups, unfortunately this park doesn’t allow them at this time. However, the other reservations listed above however do!

Recommended Trails:

• Walden Pond Path – 1.7 mi – easy – 43 min
• Mount Misery via Heywood’s Meadow Road – 4.3 mi – easy – 1 hr 56 min
• Lincoln to Walden Pond – 5.6 mi – moderate – 2 hr 34 min

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