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Fun Things To Do In Manchester By The Sea

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We often tell our guests that we view a visit to Rockport, Massachusetts as a visit to all of Cape Ann. This scenic, rocky peninsula on the north shore of Massachusetts is comprised of 4 towns: Rockport, Gloucester, Essex and Manchester By The Sea.

Each of these 4 Cape Ann towns has its own distinct character that becomes readily apparent when visiting.

So, here at Addison Choate, we have decided to put together a 4-part road trip series to share the history, character, and things to do in each of these Cape Ann towns. Today, we will take a closer look at Things To Do In Manchester By The Sea.


A Closer Look at Manchester By The Sea

Manchester By The Sea is the southernmost town on Cape Ann and has a population of approximately 5,300 residents. Originally a part of Salem, Massachusetts (like much of the north shore) Manchester was incorporated back in 1645 and sustained itself through the fishing industry for hundreds of years.

The character of the town began to change in the mid 1800’s when Boston’s elite began to construct some “modest” summer cottages along the Manchester coastline.

Things To Do In Manchester By The Sea

Originally known as plain old Manchester, the town voted to gild the lily and change the name to Manchester By The Sea. This change was, ostensibly, made to avoid confusion with other less desirable Manchesters like Manchester, NH.

To be fair, early settlers really weren’t all that original with our town names. For example, Manchester is actually a town name in New Hampshire, Massachusetts, Maine, Vermont, and Connecticut.

Today, Manchester is an elite north shore town that is regularly ranked as one of the most affluent in the state. It’s no wonder why people want to reside in town, it offers beautiful beaches, a vibrant boating community, and has coastal New England vibes aplenty.

You likely first heard of Manchester By The Sea after viewing the uplifting Kenneth Lonergan film. But now you’re coming for a visit and wondering what are some things to do in Manchester By The Sea? Well, let’s dig in!


A Little Beachcombing at Singing Beach

One of our favorite beaches on Cape Ann, Singing Beach is a beautiful, public beach and has sand that makes a unique sound when you shuffle your feet in the dry beach.

There has been much speculation as to why singing beach sings. The answer is not entirely clear, but it seems to be a combination of the humidity, witchcraft, and the elements that compose the sand grains.

Singing Beach Manchester By The Sea

We love Singing Beach because it is such a peaceful enclave. The small, semi-private parking lot keeps the beach a little quieter than some of the larger, more well-traveled beaches like Good Harbor and Crane’s Beach. The crescent-shaped beach is also backed by a large hill and rocky points on either side that really enhance that feeling of privacy.

Between Memorial Day and Labor Day there is a bathhouse with showers and a concession stand that make for a convenient and comfortable visit.

Getting to the beach itself can be a little bit of a challenge, but it’s really not all that bad. The Rockport commuter line has a stop right in the center of Manchester and from there it’s just a short 7-8 minute walk to the beach.

If you are thinking about driving to Singing Beach, we’d recommend parking in town, by the train stop. The Boy Scouts sell parking spaces there on summer weekends and you can grab a quick ice cream cone at Captain Dusty’s for the walk.


Get A Few Scoops at Captain Dusty’s

A Manchester institution, Captain Dusty’s has been serving Manchester residents and tourists since WWII.

The story of Captain Dusty’s is pretty incredible. The business was started by Bruce Leseine, a black porter who worked for a millionaire who had a private train car and home in Manchester.

During the depression, the private train stopped traveling and Bruce found himself stuck in Manchester.

Fun Things To Do IN Manchester By The Sea Massachusetts

Naturally, he turned to one of Manchester’s most abundant resources, fish and started catching and selling fish in town. He acquired a small rowboat with the money he had saved, and, over time, he was able to acquire a building and create a seafood and bait shop.

The only black resident in Manchester, Bruce would tell anxious residents that aww it’s just dust. That’s how he ended up with the name Captain Dusty.

The shack with the eponymous name is still located in the original building right at 60 Beach Street. Be sure to stop off for a treat on the way to or back from the beach! 


Pick Up A Good Book at Manchester By The Book

Manchester By The Book is a booklovers paradise and one of the best bookstores on Cape Ann. With a wide variety of new and used books to choose from and a passionate owner and employees, it is the perfect spot to stumble upon your next interesting adventure.

Manchester By The Book

Get lost in the stacks browsing the incredibly diverse array of titles or pull up a comfy chair and make yourself at home for a bit. Everything from classics to art to architecture and even children’s books fill every nook and cranny of the 27 Union Street location.

We think that Manchester By The Book is bursting at the seams with books that even Will Hunting would deem are “the right books.”


Do Some Shopping Downtown

Manchester By The Sea has that quintessential New England coastal feel. With historic shingled homes, small, winding streets and beautiful ocean views it’s a great spot to spend an afternoon.
One of our favorite shops in town has to be The Stock Exchange. Founded in 1975, The Stock Exchange prides itself on having high quality consignment goods for discerning shoppers.

Whether you are looking for a beautiful handwoven rug, antique furniture, glassware, art, or clothing, The Stock Exchange has you covered.

Another great stop while in town is 4 Beach Gift shop for all of your local gifts and goodies from local makers and MBTS gear.

If you need to refuel, you can pop into the Laughing Gull right on Summer Street for a caffeinated beverage, smoothie, or a tasty sandwich. If you are looking for something more substantial, you could head down the road to Bravo By The Sea for a nice woodfired pizza!


Delicious Woodfired Pizza at Bravo

One of our favorite pizza spots on the north shore, Bravo By The Sea serves up some delicious woodfired pizza that has a flavorful and has deliciously chewy crust.

All of the ingredients are fresh and there are a number of creative pizza options to choose from.

Bravo By The Sea Woodfired Pizza MBTS

A few of our favorites include the Classic Pepperoni, Chicken Bacon Ranch, and the Fig Prosciutto which comes with black mission fig marmalade, prosciutto, for di latte, and gorgonzola.

If you’re in Manchester, it is definitely worth a stop. Grab a pizza and head over to enjoy in Masconomo Park with a backdrop of harbor views.

Bravo also recently opened a new location right on Main Street in Gloucester, which would be another great stop if you are staying with us at Addison Choate.


Take An Aquatic Adventure

If you visit Cape Ann and don’t go in the water, did you really even visit Cape Ann? It’s worth finding unoccupied bodhi tree, curling up and pondering.

Surfari Stand Up Paddle and Surf offers stand up paddle sales, rentals, and tours all across Cape Ann. Drop your stand-up paddle right into Manchester’s inner harbor and enjoy a scenic paddle.

Surfari was founded back in 2006 and the owner was actually born and raised in Manchester. Whether you are looking to hop on a surf board or take a calm paddle, Surfari is a great option.

Another great option is to drop in kayak and head out to explore the harbor, coves, islands and shipwrecks. You could even paddle all the way out to the lighthouses and islands in Gloucester. Here is a map of this journey: http://www.scenicnewengland.net/kayak/trips/manchester/map.html

You can launch in the harbor or from Kettle Cove or one of the other beaches in town. If you need a kayak, the team at North Shore Adventure are fantastic and even offer some fun local trips like kayaking out to Straitsmouth and Thacher Islands in Rockport. Check out their website here: https://www.northshoreadventure.com/


Tee It High & Let It Fly at Essex County Club

As you drive into Manchester, right down School Street, you will find Essex County Club (ECC) on your left. There are clay and grass tennis courts and a driving range that really set the tone for your visit to this Cape Ann Town.

ECC boasts the first great Donald Ross designed golf course. Even more impressive, Donald Ross was actually the pro at the Essex County Club from 1909 until 1913 until that little golf course architect gig got in the way.

Golfing at Essex County Club

The course is undeniably beautiful. It has some unique hole layouts (in true Donald Ross fashion) and some tall fescue to add to the natural feel. It also has some interesting history. The 3rd green, dating back to 1893, is the oldest green in continuous existence in the United States. In addition, the club itself was only the 6th member of the United States Golf Association (USGA). It’s not the Old Course at St Andrews (which dates back to at least 1552), but it’s still pretty wild! 

The only catch to playing this course is you will have to have an inside connection. The club is private so you will have to befriend a member to get out on this track.


Head To Woods & Live Deliberately

One of our favorite parts of Cape Ann is all of the undisturbed nature and the thousands of acres of preserves that are right on the coastline. Manchester By The Sea, and the other towns of Cape Ann all have some incredible outdoor space to explore. We dove into some of our favorite hikes in our blog on 6 Beautiful Hikes on Cape Ann.

In Manchester, there are a couple of spots worth exploring. First, you can visit a 116 acres acre park that was formerly known as Agassiz Rock. Now known as the Monoliths, this park is home to two large glacial erratic boulders. The hike is fairly easy and a great place to spend a quiet peaceful afternoon.

Another spot to check out in Manchester is Coolidge Reservation. This 64-acre park contains a few different trails and you can take. The walk out to the large lawn right on the ocean is peaceful, fairly easy, and you will be rewarded with a beautiful view of the Boston skyline.

It is such a great hike that the Trustees of Reservations picked it as one of their favorite coastal hikes: https://thetrustees.org/place/coolidge-reservation/


Grab Some Tasty Eats

There are a few great spots for food and drink in Manchester By The Sea. One of the most popular spots in town is Cala’s Restaurant. This restaurant is a part of the Serenitee Group which has a number of restaurants on the north shore, including Minglewood in Gloucester, and Hale Street Tavern in Beverly.

Cala’s is a great spot for some tasty upscale pub food done well. You can get anything from tacos to mac and cheese, steak frites, and poke bowls. Cala’s also has a great bar to gather for drinks and a friendly and laid-back staff.


Another place to stop is Antique Table in the old 7 Central restaurant building. This building at 7 Central Street operated as the 7 Central restaurant for decades and has a storied history as a tavern, stage coach stop, and post office over the last 250 years.

Antique Table now offers diners a great variety of Italian dishes from pizzas and salads to pasta and some tasty desserts. The intimate dining area and attentive staff absolutely heighten the dining experience.

There are really so many things to do in Manchester By The Sea, but we hope that this list helps get you off on the right track when visiting this Cape Ann treasure. We will continue our series visiting all of the Cape Ann towns and hope to be a helpful virtual tour guide for your next visit!

If you stay with us at Addison Choate, in Rockport, our team of locals will happily provide you with all of the info you could possibly need on the local hot spots around Cape Ann.

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