Do you have any questions for me?
Don't wait. Call right away!

Boston offers a ton of great hikes, no matter the time of the year. You can live in Boston for decades and you may not discover all the hiking options. Here’s a look at some of the top unknown hikes you can find throughout Boston.

Ponkapoag Pond Trail

Considered an easier trail in the Blue Hills Reservation, Ponkapoag Pond Trail measures about 6.7 miles. It’s a great choice with accessibility year-round. Dogs are even welcome on this trail if they are kept on a leash.

Plum Island Hiking

A six-mile barrier island, Plum Island offers a great choice for hiking. Many don’t know about the hiking found on this island including the trails at the Parker River National Wildlife Refuge. You can bike the island or hike on foot for some incredible views.

Blue Hills Skyline Trail

A harder trail offering nearly a 12-mile loop, this trail offers plenty of fun. It’s open from March through November and both dogs and horses are welcome on this trail.

Wilson Mountain Reservation Trail

A 1.6-mile trail loop near Dedham, the Wilson Mountain Reservation Trail offers a great hike for all skill levels. It’s a good choice for birding and dogs are welcome. This trail is accessible year-round.

Blue Heron Trail

A 6.3-mile trail loop near Needham, the Blue Heron Trail offers a lake and plenty of hiking for any skill level. It’s open year-round and dogs are welcome, as long as they are on a leash.

Skyline, Sawcut Notch, Indian Camp, and Pipe Loop

A 3.7mile trail loop near Quincy, this hiking loop is often highly trafficked from March to November. The trail is open to dogs on a leash and it works for any skill level.

Secret Squantum Park Hiking

While you may know the Secret Squantum Park as a place for history, it’s also a great spot for hiking. You can walk the trails and see the many great historic sites throughout. You can even walk out to Thompson Island via the sand bar if you time it correctly.

World’s End Hiking

Worlds End Hiking

A great spot for hiking if you want a view of the Boston Skyline, World’s End offering an incredible choice in Hingham. It’s filled with character, amazing views and so much more. There are 4.5 miles of footpaths for moderate hiking and it’s open year-round.

Neponset River Greenway

An 8.2-mile trail offering plenty of beautiful views, this trail is great for all types of reasons. You can bike, skate, walk, or even cross country ski on the path. The Neponset River Greenway may not be a huge secret, but it can be overlooked and some areas are often missed by skilled hikers.

Georges Island Trails

For incredible views and plenty of history, head to Georges Island for plenty of fun hiking options. You can picnic here, take the ferry, enjoy plenty of history at Fort Warren, and so much more.

While many of these hiking options are not exactly a secret or unknown, they are not as popular as the main hiking choices. Many skilled hikers overlook these trails and the wonderful hikes they offer.

Get the free guide

10 Things Real Estate Agents Hope You Don't Ask When You Buy A Home


Avoid unpleasant surprises when you’re buying (or selling) your home.


We know how to make this an easy, straightforward process for you. Enter your info to get our list of 10 key points to make sure you are aware of as you do your research.

Thank you! Check your inbox in a moment for your guide.