Welcome to the Local Hiking Adventure Page

So many great parks here in Eastern Mass, you do not have to travel far to spend 4 - 6 hours on a rugged woodland hike adventure.

Lynn Woods Snow Adventure: Search for Forest Castle


3 Mile / 4 Hour Snow-Shoe Adventure that will satisfy all your snow + pine tree needs.

Video: Search for Forest Castle

Snow-Shoe Adventure Hike at the Lynn Woods Reservation.

Breakheart Reservation: Seven Summit Hike


Breakheart is much more than just a paved surface road.

There is some great trail hiking at Breakheart on the Ridge Line Trail, Castle Rock, Eagle Hill, and the Fox Run Trail. 

This 4 Mile, 7 Hill Hike will take 4-5 hours to complete. 

The trails are very rugged and rocky. You will need food and good hiking boots.  Do not underestimate this hike.  It is serious work to complete this hike. You will need to download the map for this one, or you will never find your way.

Video: Breakheart Reservation the Ridgeline Trail

4 Miles / 7 Summits / 4 - 5 hours of Rugged Hiking Trails. 

All inside Metro Boston.  All summits exhibit breathtaking views of everything around you.  I just happen to get a great day in October 2019 for my visit at peak foliage.  Note: Most of the Ridgeline trail is not for mountain bikes.

Hiking in Eastern Mass


Lynn Woods West-Side Hike

Lynn Woods West Side Hike: Lynn Woods is an all season park that can be enjoyed for many hours and many different activities. Part of my Eastern Mass Hiking Series, the Lynn Woods is a treasure of geology and organic splendor.


Rockport Babson Boulder Hike

The Babson Boulders Trail, Prime-Evil Forest, and South Woods Hike is a 7 mile, 4 hour adventure in the forest of Rockport, on Cape Ann. This hike is on rugged terrain.

History: Roger Babson donated 1,150 acres of Dogtown land to Gloucester in 1930. Part of his personality and values are still seen in Dogtown today. A unique aspect of Dogtown are the motto's carved in rocks. In the 1930s, Mr. Babson hired out-of-work stone engravers to inscribe a set of motto's collected mainly from the Good Cheer Library which was a set of inspirational and self help books. There are 24 motto's that are carved into some of Dogtown's larger stones.


Rockport Quarries Hike

The Rockport Quarries Hike is a great way to see some woods and see some sights that make Rockport a destination for many tourists. Rockport is Beautiful.

Expect 4 hours and near 8 miles for this hike.  This Hike starts and ends at the Rockport Train Station. So a day trip from Boston on the train is the best way to start this hike. At the end of this hike is the World Famous Motif #1

Blue Hills Hike / Best Hike Inside Metro Boston


Blue Hills Hike / Quincy

The Blue Hills is over 7500 Acres of Forest and 125 miles of trails at the Southern City Limits of Boston

This hike is on very rugged terrain. I strongly recommend real hiking boots and even hiking poles. There are lots of rock scrambles and very rocky trails.  

In all you will climb and descend 10 times on steep boulder ridden trails. The first 5 miles will be this type of terrain. The return 2 miles of trail are fire-roads and are very easy walking. Expect 4- 6 Hours for this hike with stops.

Lynn Woods Bow Ridge Hike (Best Local Hike)


Lynn Woods / The Best Park on the North Shore

Great 4-5 hour Hike over very rugged terrain. Amazing views and 1000's of unique geological rock formations. Around every corner is just WOW for what you will see.  Even if you bring your best Camera, you will not capture what you see with your eyes.

Hiking / Trail Running / Mountain Biking / Snow Shoeing / Bouldering / Strolling.  Lynn Woods has it all.

Lynn Woods - Bow Ridge Bike/Hike See the Video Adventure

This is the Video of the above described Expert Level MTB Ride / Technical Hike.

Boston's Best Walkabout: The First 5 Miles of an All Day Adventure


Bostons Best Inner City Adventure

 Get your best walking shoes on, and head to the last stop on the Orange Line. Forest Hills. In the heart of the City, you are surrounded by trees. You will not feel like you are in a big city like Boston on this walk.

Expect to spend 5 - 8 hours on this walk-about. Pack a lunch.   

See the MAP LINK at the bottom of this section.

(Map shown sideways)


St Michael's and Forest Hills


The WOW Factor is off the scale in these 2 Cemeteries.   The photo-show is mostly from St.Michael's.  These folks put a lot of thought into their final spots.

Forest Hills has a Natural Beauty that is also stunning. Expect to spend a lot of time at these two places. There are many peaceful paths and places to tread. Take your time and read some epitaphs. 


The Arnold Arboretum


The Arnold Arboretum is a quiet place in the middle of the city. I mapped for you a couple of small walking paths, and a climb to the top of Bussey Hill to oversee the entire area and the Boston Skyline. A great place for your lunch stop.

Option: You can end your walk here, and head back to the Orange Line Forest Hills Stop. (5 Miles Total)

Jamaica Way and the Fenway: The Second 5 Miles


Jamaica Pond and the Jamaica Way


If you decide on the whole 10 miles...

On exit from the Arboretum, you head down a short section of roadway on the Arborway, and enter the Jamaica Pond area.  You will find many small paths that go along the water, feel free to wander off the GPS route.


The Fenway and Victory Gardens

 The rest of this walk is amazing. There are little dirt paths and walkways all over. You are in the woods, with the busy Boston City-life going on all around you. 

The Victory Gardens are a Public Space where many Bostonian's have there private yard space.  Small walking dirt paths litter this area, and you can spend an hour going up and down each path.


Time to Eat

This is a long day of walking. You earned whatever you want to eat. This tour ends at the Pru-Center, and Newbury Street. Probably 50+ places to eat. Plan ahead. 

Eataly is in the Pru-Center. A place where many food Artisans have small shops.

Here is a link to the 10 Mile Boston Walkabout