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Fall In Rockport Massachusetts – The Best Kept Secret

Well, this morning we reached a milestone. As the cool air came rushing in our open window, I reached into the closet and pulled out my faithful old Patagonia vest for the first time in months. A clear signal that fall has officially arrived in Rockport, Massachusetts.

Fall in Rockport Massachusetts

But, not to fret, fall is a fantastic time for travel and a great season to visit Rockport. The scenic coastal village becomes more peaceful, after Labor Day, and you almost feel like a local when you wander through the streets and along the scenic coastline.

Let’s take a closer look at some reasons to visit Rockport in the Fall.


Fall Leaf Peeping

Cape Ann and Rockport are fantastic locations to get your leaf peeping on. Scenic Route 127 offers a great drive where you can take advantage of many beautiful vistas, enjoy the salt air, and maybe even drop the top if you are lucky!  127 winds through the towns of Beverly, Manchester By The Sea, Rockport and Gloucester, and is the perfect embodiment of the merits in taking the long way home.

If you’re feeling more adventurous, you can also set out on foot to witness the glory of fading chlorophyl and majesty of the colors that emerge from the local plant life. Trusty camera in hand you can head to Halibut State Park, Ravenswood Park, The Headlands or Dogtown Commons to get up close and personal with mother nature.


Peruse Incredible Art Galleries

The fall is an exciting time for artists in Rockport because it’s the time of the annual Cape Ann Plein Air Festival. You can witness artists wandering the local shorelines and estuaries with easel and paint in hand to capture the stunning landscapes on the north shore.

Rockport and Gloucester are also home to an incredible number of art galleries that you can visit, peruse a wide variety of artwork, and meet the talented local artists on Cape Ann. You can even add some of their work to your collection!


Witness The Work of Talented Makers

In addition to painters, there are a variety of fun shops that you can visit in Rockport. You can try your hand at making a candle at Rockport Candle Company, you could witness glassblowing at the impressive new shop, Cleod Glassworks, or view the ocean-inspired pottery of Cynthia Curtis.

Cleod Glass Making

Another popular shop is the print shop, Rusty & Ingrid. Their vintage screen prints are all handmade and capture the beauty and dynamic landscape of New England. That is just scratching the surface, there is so much to dig into and learn about that Rockport is the perfect place for the curious traveler.


Learn Local History 

The north shore of Massachusetts has a rich maritime history and local museums such as the Cape Ann Museum are the perfect way to walk through Cape Ann’s past and present and gain a better understanding of this beloved Massachusetts destination.

From Rockport’s quarrying past to Gloucester’s storied fishing industry, it’s all on display at places like the Cape Ann Museum, the Essex Ship Building Museum and even at the Peabody Essex Museum in Salem. 


Indulge In Some Tasty Treats

If your blood sugar starts getting into the danger zone, fear not, there are many tasty treats to be had in Rockport.

Some great options include Rockin’ Cupcakes, The Fudgery, Bean & Leaf Café, Helmut’s Strudel, and Brother’s Brew Donuts. Do we have healthy food in Rockport? Sure some, but you’re on vacation and it’s time to treat yourself!

The Fudgery Rockport MA

Plus with hibernation season on the way you need to be sure that you stay warm and fueled for the winter months that lay ahead. If you’re looking for a more substantial meal for lunch or dinner there are many great restaurants too. Take a peek at some of our favorite restaurants on Cape Ann


Tour Hammond Castle

On a rocky cliff overlooking Gloucester Harbor you will find Hammond Castle, home of the eccentric inventor John Hays Hammond Jr. holder of over 400 patents, Hammond was known as the father of remote control.

Hammond Castle in the Fall

On the tour you will be able to view Hammond’s fascination with the Renaissance, his his impressive pipe organ, and learn about his infamous hijinks.

Halloween was Hammond’s favorite time of year and In October you can take a haunted tour of the castle on the weekends. Perfect for those looking for some eerie fun!


Take A Day Trip To Salem

So it’s Fall in Rockport and fall means Halloween. Just so happens that we are a quick drive and just a few train stops from the Halloween capitol of the world, Salem, Massachusetts.
Whether you’re looking to restock your potion cabinet, give a new wand a chance to find you, or get the lowdown on the infamous witch trials, Salem is a fantastic day trip.

The beautiful coastal town was once one of the busiest port cities in the entire country and has a fantastic history. While you’re in Salem be sure to stop by the Peabody Essex museum, it’s a world class museum that is well worth a visit.


Sunflower Fields Forever

In Chinese culture, sunflowers are said to symbolize good luck and lasting happiness. In that case, you are assured lifelong luck and happiness upon visiting Colby Farm or School Street Sunflowers!

Sunflower Fields in the Fall

You can also get your New England apple picking experience at Russell Orchards in Ipswich, MA. Taste the different apple varieties, drink fresh cider and enjoy some apple cider donuts. One of the benefits to taking advantage of the fall in Rockport, Massachusetts is that you can experience all of the beauty and sights across the entire north shore! 


Delicious Seafood

If you’re a seafood junkie, not to worry, Rockport has your fix! The seafood comes right out of the ocean, into Rockport Harbor, and into the restaurants back doors. No middleman necessary. It really can’t get any fresher than that!

Some great local stops include Roy Moore’s Fish Shack, My Place By The Sea, Feather & Wedge and Brackett’s Oceanview. If you’re looking to pick up some seafood for the road, we’d recommend checking out Connolly’s, Turner’s or Captain Joe’s in Gloucester.


Whale Watches

While you’re on Cape Ann you have to get out on the ocean and what better thing to do than to see some whales out in their natural habitat. From Minke to Humpback and many other species you will get to witness breaches, tails, and if you’re lucky bubble nets!

Fall in Rockport Whale Watching

Both Cape Ann Whale Watch and Seven Seas Whale Watch offer whale watches in October. If you decide to go out on a watch with Cape Ann you can take advantage of the Addison Choate Whale Watch Discount! 


Get Out On The Trails

Get outside and enjoy the incredible trail network across the north shore! From Beverly to Manchester By The Sea to Rockport and Gloucester. The north shore of Massachusetts has a surprisingly large and diverse network of trails that are perfect for trail runners dreaming of their first ultra or mountain bikers looking for that next great ride.

The trails range from easy beginner trails to trails that would challenge the most seasoned bikers and runners. The fall weather offers the perfect time to explore these networks without feeling like you need and ice bath to recover! 


Fall in Love With Rockport 

We hope that we have piqued your interest in visiting Rockport in the fall. The vibrant coastal village is fun explore in a different light and peaceful season is the perfect time for a quick escape. If you have any additional questions please feel free to reach out to our team here at Addison Choate. We would be happy to answer any questions and help point you in the right direction to enjoy fall in Rockport, Massachusetts. 


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