Checkout some of the different sailing opportunities on Cape Ann! Companies below vary from educational and historic sails to private charters. There’s no better way to take advantage of Cape Ann’s beautiful location than to get out on the water!
Frayed Knot Sailing
Ashland Ave, Manchester
23 Harbor Loop, Gloucester
33 Harbor Loop at Maritime Gloucester
Defiance Sail Charters
211 East Main Street-Beacon Marine Basin, Gloucester
Schooner Thomas E. Lannon
63-R Rogers Street
Route 127 to Beach Street, Manchester
This immaculate beach will have you singing as you look at the clear blue waters and white sands. Enjoy a thirst quenching Slurpie or Italian ice at the snack bar.
- The parking area is for residents only so you may have to walk from the train station or the center of town to enjoy this beach. Just under a mile, everyone does it!
- $5 walk-on fee.
- Directions: Route 127 to downtown Manchester to Beach Street (near the commuter rail station). Singing Beach is located at the end of Beach Street.
#1 WATCH THE BIGGEST MAMMALS ON THE PLANET
Make sure whale watching goes on your bucket list. People say: “It’s a lifelong dream fulfilled,” “It’s the best thing I ever did,” and “It made me cry,” reports Paul Frontierro of Gloucester, who has never tired of running whale watches for almost 30 years. Every single day is different. You might see mothers and calves, or whales breaching, flipper slapping, blowing or tail lobbing. On an extraordinary day, you could see 40 or 50 whales. Seasoned whale watchers go out several times a year.
#2 SOAK UP CULTURE AT THE SHALIN LIU
Like a fairytale palace with perfect acoustics, the Shalin Liu Performance Center rises from the Rockport waterfront. Its huge oceanfront windows let you watch the sun set over the harbor behind the performers while enjoying concerts of all stripes, plays, high def Met simulcasts and film festivals. What’s not to love?
#3 DIG DOGTOWN
A wild, mysterious wood blankets Cape Ann’s vast middle, a place of storied ghosts, pirates and murder. All that’s left are cellar holes and words painted on boulders: “Courage,” “Never try, never win.” So you don’t get lost, join a tour (contact the Chamber), or park on Cherry Street at Dogtown Road in Gloucester and follow the fire roads in and back. Don’t go late in the day. Bring your cell.
#4 VISIT “THE ANTIQUES CAPITAL OF AMERICA”
So many antiques shops crowd Essex’s waterfront on Rt. 133 that you’ll have to pick and choose: Americana, white elephants, fine art, European imports, something for everyone’s collection. When you weary of shopping, sample the seafood establishments also lining Rt. 133.
#5 BEACH IT UP
We have them all: spectacular barrier beaches like Wingaersheek and Good Harbor; shallow, child-friendly beaches like Rockport’s Front Beach; a beach with a dune made entirely of rocks, and even a beach that sings. Take your pick. Just don’t forget your camera.
#6 DINE WITH A VIEW
If you love seafood the way we do, you’ll love it even more with a view. You can have lobster in the rough at a rocky cove, elegant linen service overlooking the ocean, and everything in between. Bon appétit.
#7 COME FOR CHRISTMAS, STAY FOR WINTER
Nothing stops Rockport’s town tree lighting, not even a nor’easter. Santa comes by lobster boat, you can watch candy canes being made by hand, and see a live nativity with real animals, a torchlight procession, and a community carol sing. In Gloucester, Santa parades from the State Fish Pier all the way down Main Street to Stacy Boulevard for their tree lighting, and the Middle Street Walk shows off period houses. A Christmas tree made entirely of lobster traps glows above Main Street.
Essex has a Toy Land Parade, Santa’s arrival at the town landing, and breakfast with Santa.
Christmas by the Sea in Manchester finds open houses in the shops, the Jingle Bell Walk,
and the lighting of the Friendship Tree.
Rockport hosts an alcohol-free New Year’s Eve celebration throughout downtown, with clowns and puppets for children, and every kind of musical concert imaginable, from jazz, rock and roll and country and western to classical, Cajun and sea chanteys.
Between New Year’s and spring, you can enjoy some spectacular winter birding, snowshoeing, and walks in the woods. Others enjoy mountain biking in the snow, surfing the winter waves, or just plain storm watching. The less adventurous might prefer to book an inn and curl up in front of a toasty fire, hot mulled cider in hand.
Author: Patricia Mandell
King Charles I named our Cape about 400 years ago in honor of his Mother, Ann. Today Cape Ann is quickly becoming recognized as a not-so- hidden gem whose qualities and attractions improve every year. Cape Ann uniquely possesses all the best of what New England has to offer, in a compact and easily traversed area. From its expansive green saltmarshes in Essex and Gloucester and incredibly beautiful and historic harbors of Gloucester, Manchester-by-the-Sea and Rockport, to its wide, pristine beaches, and amazing rocky coastline, Cape Ann truly has it all.
Savor a relaxing porch-front view of the Atlantic Ocean at an historic inn or upscale hotel along the Gloucester and Rockport shores, walk along beautiful, wide open beaches, find unique and fun shopping, and experience a vast array of dining experiences in all four Cape Ann communities. Cape Ann is famed for the best fried and steamed clams in the region, and visitors have an array of dining options from eat-in-the rough lobsters and clams to fine dining establishments. Shop at unique boutique stores, cast-off from a dock and sail around spectacular harbors and travel farther out to the famed Stellwagen Bank for incredible whale watching and deep sea fishing. See world class art, dig into history and enjoy the stories of our earliest settlers whose homes remain intact to this day.
(Photo Credit: Arlene Taliadoros)
As the birthplace of the fried clam, this picturesque community yields some of the finest seafood on Cape Ann. Whether you care for a cup of clam chowder or a plate full of steamed clams, you will not be disappointed. But the quiet town of just over 3,000 residents has much more to offer than great seafood. Antiquing, a premier Essex attraction for generations, remains a favorite pastime for the locals as well as visitors. Shipbuilding has been part of Essex’s heritage for more than 400 years, and draws people from far and wide to admire what it takes to build the beautiful watercraft, some still sailing Cape Ann’s harbors and waterways today! The Essex Shipbuilding Museum is one stop that is a must see to truly appreciate the incredible ship building heritage of this small community. Kayaking or taking a cruise down the Essex River will surely give you a unique view of the tidal salt marsh as you meander with the river out toward Conomo Point and Ipswich Bay.
(Photo Credit: Cape Ann Chamber)
America’s oldest Seaport, this city of nearly 30,000 residents has a storied history that in the late 19th Century was the fishing center for North America. . Fishing is still a way of life for many in Gloucester and a majority of the local restaurants relying on the hard work done at sea and the fresh catch that comes in daily. Like its neighbor Essex, many of Cape Ann’s historic fishing vessels and schooners were built in Gloucester, where reputedly the first one was assembled in 1713. Take a stroll along the HarborWalk and Gloucester’s authentic working waterfront, visit the panoramic vistas of Gloucester Harbor at the Fishermen’s Memorial Statue (The Man at the Wheel) on Stacey Boulevard or from Stage Fort Park, tour Rocky Neck and its art colony and cultural district, and take to the water with a fun sail or motor tour around Gloucester’s historic and beautiful Harbor, or venture farther off shore and experience the best whale watching and deep sea fishing in New England, All this and more provide a varied taste of Gloucester’s amazing history, incredible beauty, and abundant attractions.
(Photo Credit: David Stotzer)
Founded as Jeffrey’s Creek in the mid-1800s, this town is located at the southern end of Cape Ann. In 1989 the state legislature made the name official as a means to differentiate the town from its larger neighbor to the North. A trip to Singing Beach, aptly named because of how the sand resonates when you walk on it, or Tuck’s Point is worth your time and then some. Beautiful retail shops, restaurants and galleries fill the town of just over 5,000 residents. The Manchester Historical Museum’s Trask House is a must-see to get the complete story of this town known for its beautiful historic architecture.
This picturesque seaside village, located at the most northeasterly part of Cape Ann, features beautiful beaches, historic lighthouses and galleries galore. Rockport’s downtown area is filled with quaint shops that include bookstores, candy-making, cafés and ice cream shops as well as art galleries, specialty shops, jewelers and many places to dine. A leisurely stroll along the ever-changing Bearskin Neck will give visitors every imaginable opportunity to buy that perfect keepsake to remember and cherish their time on Cape Ann. Visit Halibut Point State Park or walk along Rockport’s scenic shores in the footsteps of Ralph Waldo Emerson and Henry David Thoreau and be captivated as they were by Rockport’s special places and unique charm.
(Photo by Cape Ann Photography)
Unlike the “other Cape” in Massachusetts of Cape Cod, the peninsula of Cape Ann is truly a hidden gem whose qualities and attractions just keep getting better. With wide scale preservation efforts of marshlands, beaches, and historic areas; limited development, signage or unruly changes, the fine points of Cape Ann are quickly surpassing other tourist destinations. Our region is – in fact – so pristine that Cape Ann has become a favorite location for Hollywood movie productions because of its unspoiled landscapes and beauty.
Visitors find that they can both savor a relaxing porch front view of the Atlantic Ocean at an historic Inn along the Rockport shore, walk along pristine, wide open beaches or dine at quaint, family-owned restaurant. Cape Ann has by far the best clams in the region and guests have many options from clam shacks to gourmet eateries. They can shop at unique boutique stores, they can cast off a dock and sail around spectacular harbors, see world class art, dig into history and enjoy the stories of our earliest settlers whose homes remain intact to this day.
So, turn your wheel toward Cape Ann this season – it is both easier to reach by car or train than other New England destinations and it offers the best of all worlds.
By road, the best way to see Cape Ann is to travel along our scenic roadways. Starting – for example – by exiting route 128 or major highways and traveling along a famous coastal road locals simply call rte. 127. This road takes one past beautiful estates that lead to the sea and give an unprecedented view of our region.
Rte. 127 passes through the town of Manchester-by-the-Sea with its fine 17th and 18th century homes along its historic downtown area. By road, visitors can stop at Masconomet Park and enjoy the view of Manchester harbor or lunch at a number of great bistros and established restaurants and finish that off with a homemade ice cream from Captain Dusty’s. Many visitors like to park and walk to famous Singing Beach – where the sand literally “sings” and the gradual sloping beach gives way to beautiful views of the rocky Cape Ann coastline. From Singing Beach, continue back to rte. 127 and pass the community of Magnolia – famous for its coastal views, artist colony and summer dwellers. Rte. 127 veers off at famous Hammond Castle in Magnolia which is well worth a visit. Back on the route, one passes Ravenswood Park which offers unspoiled woods to walk in and a nature center that caters to children. Veering off rte. 127 at the Gloucester city line gives way to the magnificent overview of Gloucester harbor, seen from historic Stage Fort Park. The route takes tourists along the famous Gloucester boulevard which overlooks Gloucester’s eastern shore and outer harbor. In summer, the outer harbor is full of sailing craft and fishing boats – and three schooners that take passengers sailing: the Thomas E. Lannon, the Schooner Ardelle and the Schooner Adventure.
After stopping to see the sights in Gloucester, continue along rte. 127A to either beautiful Good Harbor Beach and the eastern shore of Gloucester or on to historic Rockport. Rockport remains the quintessential artists’ retreat and quaint coastal New England town. It is a perennial favorite and its penny candy store, art galleries, and boutiques along the roads of historic Rockport and Bearskin Neck give way to exquisite seaside Inns and bed and breakfasts tucked along the rocky shore – far from the bustle of downtown.
From Rockport, this same route leads visitors around the peninsula of Cape Ann passing Halibut Point National Park, the laid back town of Lanesville and the historic harbor at Annisquam. Halibut Point is unique geographically and offers wonderful flat rocks – left over from the days of the granite quarries – which make a perfect picnic spot by the sea.
Exiting the Cape Ann peninsula – there is still more to see by traveling along rte. 133 towards Essex . Rte. 133 (which literally connects the Cape Ann peninsula with the river towns of Essex and Ipswich along Ipswich Bay) is where visitors can stop at both Wingarsheek Beach and the historic town of Essex, famous for its shipbuilding and Essex clams. Drop by the Essex Shipbuilding Museum and learn about this town’s rich contribution to our colonial history – whose ships built along the riverbanks populated the Gloucester fishing fleet from the 1600s to the days of Captain’s Courageous written by Rudyard Kipling and to the present day with three Essex-built schooners plying the tourist trade in Gloucester harbor.
Although not technically considered Cape Ann, if you continue on to historic Ipswich with both its gorgeous Crane Beach reached along rte. 133, historic apple orchards, historic homes and great local restaurants.
Cape Ann is not only a perfect place to see by road, it also offers its share of water tours including river and kayak tours of the pristine Essex River and its outlying beauty that features Hog Island and Crane Beach. The famous movie the “Crucible” was filmed on Hog Island and there is are two river boat companies as well as kayak rentals on rte. 133. Whereas in Gloucester one can sail on an Essex built schooner, in Essex one can paddle or poke along a tidal river viewing marsh birds, seals, and unspoiled vistas. It is the best of both worlds.
You already know you can enjoy the freshest seafood around when dining on Cape Ann. But, what dining experiences might surprise and delight you?
In Rockport you can expect to buy a freshly steamed whole lobster at Roy Moore Lobster Company. But, why not enjoy it while sitting on the rocks at the end of Bearskin Neck? The chefs at Roy Moore’s make it easy for you by cracking the lobster, and throwing in melted butter and lemon. Once settled on the rocks, surrounded by the deep blue waters of the Atlantic, you’ll never want to leave.
Just a few minutes away in Gloucester, you’ll find culinary adventure at every corner. Stop by the Azorean Restaurant for Portuguese style cuisine, a full bar and a diverse menu. Ever try octopus? Now’s your chance. They brush the octopus with olive oil, grill it, and drizzle with garlic spiced oil. It only takes one bite to convince diners that it’s a good thing to be adventurous when dining out.
What about a dining adventure on the water? Gloucester offers dinner cruises on the Beauport Princess. You can find out more information by visiting cruiseportgloucester.com.
Essex is the home to America’s first fried clam. But where might you want to stop before your clam dinner? How about enjoying a before dinner drink? Just across the street from Woodman’s is Shea’s Riverside Restaurant & Bar, where you can sit on the deck, and watch the Essex River wind towards the Atlantic. The peaceful scene will relax your mind and soul.
What if you’re looking for a guaranteed good dinner and a livelier night, but nothing too crazy? You might be surprised to hear 7 Central in Manchester by-the-Sea not only offers some of the best comfort food around (Shepherd’s Pie, Macaroni and Cheese, Braised Spare Ribs) but also trivia nights, acoustic music and karaoke–all in the atmosphere of an old New England inn.
Visit Cape Ann for the reasons you always visit, the fresh seafood, beautiful coastline, family friendly beaches, and authentic people. Just remember to keep your minds and appetites ready, for the unexpected culinary adventures of Cape Ann.
Author: Terry Weber Mangos
If you’re looking for things to do and breathtaking places to explore, Cape Ann is where you need to be! One of our favorite spots is Coolidge Reservation in Manchester-by-the-Sea.
Enjoy the View at Coolidge Reservation: Within its 66 acres, breathtaking vistas await as you explore rocky outcrops, woodlands, wetlands, a sandy beach, and the open expanse of the Ocean Lawn.
Summer Street (Rt. 127), Manchester-by-the-Sea. 978-526-8687.
Written by Patricia Mandell
The carefree hot summer days with warm sand, surf and endless ice cream may have come to an end but with the abundance of beautiful beaches on Cape Ann, the colder months are still great for a crisp beach walk or sightseeing. You may find a new hidden gem to keep coming back to all year!
Good Harbor: Rt. 127 A Thatcher Rd
One of the most popular beaches on Cape Ann for its spacious size, soft white sands, and view of the Atlantic, Good Harbor Beach is a great beach for anyone to enjoy!
Wingaersheek Beach: Rt. 133 to Concord Street Exit 13 to Atlantic Street
Nestled by the Ipswich bay and Annsiquam River, Wingaersheek Beach hosts spectacular views of Cape Ann. The beautiful large terrain of the beach makes for tide pools and large rocks that children and adults can all enjoy.
Cressy’s Beach and Half Moon Beach, Stage Fort Park: Western Ave (Rt. 127) to Hough Ave
What better way to spend a day than at both Stage Fort Park and the beach. Cressy Beach encompasses a spectacular view of Gloucester Harbor with its rocky coast. The park area by the beach has large grassy lawns that make for great picnics in the summer months. Half Moon Beach is a more quaint, quiet area with an abundance of shady spots. This is the perfect beach to view the harbor and park in a more secluded way.
Pavilion Beach: Western Ave, the end of Stacey Boulevard
Located central to downtown Gloucester and many famous historic landmarks, including The Man at the Wheel, Pavilion Beach is the perfect place to unwind and relax after a day of exploring everything Gloucester has to offer!
Niles Beach: Eastern Point Rd
One of the quieter, less crowded beaches in Gloucester, Niles Beach is a nice hidden gem. Although it is a resident only beach, if parking can be found elsewhere you can walk on. The beach boasts views of Gloucester Harbor and the Boston skyline in the distance.
Plum Cove: Rt. 127 near Lanesville
This quaint little beach located right on Ipswich Bay is ideal for children and families. Resident stickers are also required at this beach for parking.
Front Beach: Off of 127A take Main St. to Beach St. to downtown Rockport
Surrounded by an abundance of Inn’s and B&B’s Front Beach is in the perfect location. This is a great spot for swimming, especially during high tide as much of the beach is overtaken by water. Also in close proximity to downtown with tons of restaurants and shops!
Pebble Beach: Penzance Rd
This beach stays true to its name as it is covered in a variety of smooth pebbles and stones. Pebble Beach is the perfect place to search for seashells and view all of the sea birds that fly about. The Boston skyline can also be seen in the Southwest direction.
Cape Hedge Beach: South Street
Cape Hedge Beach is a very quiet beach with a long rocky shore. The beach sits about 2.5 miles from downtown Rockport.
Long Beach: Thatcher Rd to Rockport Rd- 127 A
Long Beach is the perfect quintessential New England beach with views of the Twin Lights on Thatcher Island. The beach is also surrounded by a variety of Inn’s, B&B’s and beautiful New England style homes.
Singing Beach: Beach Street, off Rt. 127
This beautiful spacious beach is one of the hidden gems of Cape Ann with its soft sand and deep blue waters. Although parking requires resident stickers most park at the train station and walk on ($5 walk on fee).