top of page
  • Writer's pictureKatie Grillo

Boston Area Hiking

Updated: Feb 16, 2022

Beautiful Hikes in the Greater Boston Area

Hammock Time at John Tinker

I am sitting... in my hammock. I know, I know, this isn't something you normally do when on a hike, but given the opportunity, I'll always take a moment to slow down and enjoy a particularly beautiful spot. Today's hike led us through dense woods, into a patch of tall thin pines that danced together in the gentle breeze. The water was calm and the sun in early Spring felt like a kiss of heaven on my winter skin.

When searching for the next hiking trail, I almost always look for a place near water. Maybe it's a product of living in a dense city, or maybe it's a bit of nostalgia, but there is something about the water that is so calming and peaceful to me. This guide will highlight a variety of different hikes in and around the Boston area. Most hikes are categorized as easy, with minimal elevation gain and a length of under 5 miles.



Lots of Rivers, Lakes, and Ponds -- Beautiful Trails outside of a busy city - Lightly Trafficked Trails

Local trails organized by distance from Boston, MA.

Each point on the map includes a number of photos from the hike and any maps or trail routes that we took. I use to find most of these locations. My search filters were set to areas with minimal elevation gain and low traffic (trying to social distance during Covid times). This map is a constant work in progress. Come back often to see what new hikes I've added to the map!

Map Happy Travel Guides

As you can see, there are a lot of options for hikes around Boston! It's hard to pick a favorite, but here are a few top recommendations:

Beaver Activity at Harold Parker

Harold Parker

Lots of flat trails alongside multiple ponds. This was one of the few spots that we actually returned to as opposed to searching to find somewhere new. The trails are very easy to follow as they wrap around the pond. There is lots of beaver activity (although we never actually saw a beaver). The cut logs and beaver dams made the hike even more interesting.

Tall pines at John Tinker

John Tinker

This location is a little bit further outside the City (designated by the red color on the map), but it is worth the drive. The trails are beautiful and there are tons of birds on the lake. The tall pines were some of my favorites that we saw on all of our hikes.

Tips and Tricks


All of the trails we visited (with the exception of a few - see map for details) were free to enter and offered free parking. Some of the lots were small and could only accommodate a few cars. I recommend getting an early start to the day. The woods are so peaceful in the morning. Plus, you'll have a better chance at getting those prime parking spaces!

Waterproof boots

Lots of these hikes were done in the early Spring. Waterproof boots were a necessity in many of the areas. There were areas of minor flooding and just muddy trails at times. Nothing to worry about when you have good footwear!

GPS and Cell Service

Most of the trails had adequate GPS and cell service. That being said, make sure you are prepared. I'll leave you with one of my favorite quotes,

"The best time to have a map is before you enter the woods."

-- Brendon Burchard

Future Hikes

This map is a constant work in progress.

Come back often to see what new hikes I've added to the map!

Katie’s Visit Info

Travel Dates

Spring, Summer and Fall of 2020

Travel Info

Short drives from Boston, MA

Car required for most locations

Travel Buddies

My husband Mark accompanied me on all of these hikes. We also did a few social distancing hikes with friends who live out in Western, MA (shout out to Sebbie and Suparna, Valerie and Alec, and Deb, Craig and Sam).

94 views1 comment

Recent Posts

See All



bottom of page