#makeadventure Massachusetts Edition

massachusetts #makeadventure

After living in Pennsylvania for the first 22 years of my life, I found myself packing my things for my big move to Massachusetts, often referred to as the Bay State. I will freely admit that I was not really looking forward to the move. I was accustomed to rural Pennsylvania with its rolling rocky hills, numerous farmlands and spread out towns. When I thought of Massachusetts all I pictured was Boston, a high population density and lots of traffic. During my time here, however, I was proven wrong time and time again. Massachusetts has a great diversity of things to do and see that will keep you busy for years.

I could probably write a book detailing all the things to do here in the Bay State, but alas, AAA has beaten me to it. No big deal though. Have you looked at one of those AAA guidebooks lately? I have and was so overwhelmed with information that I closed the book vowing to never look at it again. Where’s the “best of Massachusetts” section? Have no fear, I created that section for you in this article. To be fair, I am an avid backpacker and ultrarunner so the list is a little skewed towards trails. If trails are not your thing, I have included a few other options as well. Basically, my list is categorized by regions with each region detailing my top 3 choices for things to do while there.


Mt. Greylock

Mt. Greylock is the highest mountain in the state, standing at 3,491 ft. On the summit stands a 93 ft tall lighthouse that provides 360 degree views to the nearby valleys and the not-too-distant mountains of New York and Vermont. If you are looking for trails, you will not have to look too far with almost 70 miles of them crisscrossing the mountain. Looking for a backcountry campsite? Check out the primitive backcountry area that is rated one of the best in the nation. If you don’t have much free time, you can take the auto road almost all the way to the summit.

#makeadventure Massachusetts Greylock lighthouse
Mt. Greylock Lighthouse


Upper Goose Pond

Upper Goose Pond is located along the Appalachian Trail just south of Lee, MA. A short walk from nearby Rte. 20 will get you there in about an hour or so. You can even kayak or canoe in from nearby Goose Pond. Once there, you can swim in the refreshing mountain lake or troll the lake in your watercraft. This spot also makes a great place to camp as the Appalachian Mountain Club has a cabin there along with campsites.

#makeadventure Massachusetts upper goose pond
Looking out over Upper Goose Pond


Norman Rockwell Museum

Located in Stockbridge, the museum is set on the land that Normal lived for the last 25 years of his life. It has the world’s largest collection of Rockwell art. You can also tour his studio while there which overlooks the nearby valley. If you are into folk music, the town of Stockbridge might ring a bell. It was the home of Alice’s Restaurant that Arlo Guthrie made famous. Sadly, the restaurant has been renamed, but you can still find it just a half a mile from the railroad tracks in downtown Stockbridge.

Normal Rockwell Studio #makeadventure Massachusetts
Normal Rockwell Studio



Massachusetts MidState Trail

Looking for a long distance backpacking adventure or some short day hikes? Check out this 92 mile long trail that runs from the Rhode Island border to the New Hampshire border. You will be presented with a variety of terrain from rocks, hardwood forests, fields and mountain vistas. At Mt. Wachusett, you can even see the Boston landscape some 40+ miles away. The trail also runs by Barre Falls Dam, home to an awesome frolf course.

#makeadventure Massachusetts
Mt. Watatic on the MA MidState Trail


Mt. Wachusett

Yes, I know I already mentioned it, but it deserves its own section. Besides views of Boston and the MidState Trail, the mountain is home to 17 miles of hiking trails and is a popular spot for nearby trail runners for hill workouts. The mountain also offers 22 ski trails in the winter. Don’t expect a top-notch ski adventure, but it certainly works well if you find yourself nearby in the winter with little time to travel elsewhere.


mt wachusett #makeadventure Massachusetts
Mt. Wachusett Welcome Sign


Hanover Theatre

Located in Worcester, this theatre built in 1904 is home to some great shows. Both local and national touring acts can be found here along with a restored theatre that takes you back to the olden times. Combine a show with one of the numerous dining options Worcester has to offer and you will have a great night out.


The Freedom Trail

This 2.5 mile long brick-lined trail offers a great walking tour of historic Boston. You will tour such places as the cemeteries where America’s forefathers are buried, Paul Revere’s home and the Old North Church where Paul signaled that the British were coming. I take all of my guests visiting the area for the first time on this trail. No complains yet! Well, maybe one…that I walk too fast!


Freedom trail #makeadventure Massachusetts
Freedom Trail Marker


Cape Ann

Many locals swear that Cape Ann is better than Cape Cod. I would have to agree. Located about 30 miles northeast of Boston, the Cape offers numerous rocky shorelines for exploring. If the water is not too cold, take a dip in the ocean. Not into swimming? There are several coastal hiking areas such as Ravenswood and Halibut Point. Don’t forget about whale watching while you are here. My personal favorite place in Cape Ann? Cape Ann Brewing Company.

Cape Ann Massachusetts
Sunset over Cape Ann


Brewery Tour

Speaking of breweries, the Boston area is home to 2 well-known breweries, Sam Adams and Harpoon. Both places offer tours and my favorite…beer samples. Actually, the entire state is peppered with great local breweries as well. In the west my favorite is Berkshire Brewing Company. Central area would be Wormtown Brewery. Despite having Sam Adams and Harpoon, my vote in the east is The Tap Brewing Company.


So there you have it, 9 things to #makeadventure while you are in the Bay State. Who knows, maybe I will see you around? If not, happy travels!

Russ Dresher, along with my wife Niki, is the blogger behind the curtains at Backpacking Engineer. Together, we provide a wide variety of topics on our site relating to backpacking, ultrarunning and other outdoor activities. Probably the most unique aspect of Backpacking Engineer is the “An Engineer’s Guide” blogs. In these blogs, I get a little technical, a little engineering-ish with regards to the backpacking gear we all have come to love and cherish. Realizing that nerdy details are not everyone’s cup of tea, we tackle many other topics such as gear reviews, trail recipes and tips and tricks of the trade. We also maintain an informal trail journal such that you can follow our journeys.

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