For the 50+ Traveler

Elegantly sprawling homes perched on rocky shorelines with expansive ocean-view lawns line the coast of Manchester-by-the-Sea. With casual seaside charm, the village imbues a friendly warmth paired with luxurious sophistication. It is a classic, adorable New England coastal town.

Beginning life as a fishing village, Manchester-by-the-Sea soon became a summer playground for the rich and famous. Well known for gorgeous seaside resorts and elaborate summer cottages, Manchester-by-the-Sea still maintains a quaint, cozy seaside village charm. Originally named Manchester, the town was renamed Manchester-by-the-Sea in the 1980s to avoid confusion with their neighbors, Manchester, New Hampshire, which, by the way, is not by the sea.

Manchester-by-the-Sea became a re-discovered destination when the film by the same name was released in 2016. Starring Casey Affleck and Michelle Williams, the award-winning movie was filmed around the Cape Ann area, which encompasses Manchester-by-the-Sea, Gloucester, and Rockport.

Singing Beach in Manchester-By-The-Sea, Massachusetts.

1. Hear The Sand Singing Beneath Your Feet

Sparkling sand and very cold water are the calling card of Massachusetts beaches, and Manchester-by-the-sea offers two great options.

White Beach faces southwest with views of the Boston skyline beyond your view of Massachusetts Bay. Head down in the late afternoon and secure your spot to gaze at a brilliant sunset as it slips over the city.

Singing Beach beckons you to walk along the famed sand, so named because the sand “sings” when you walk on it. This phenomenon happens in just the most perfect conditions. When you scuff across the dry sand, your feet cause friction on sand that is almost perfectly round and just the right size. The sand must also contain silica to create this interesting sensation. When all of these very special conditions come together, it causes the sand to “sing” or “squeak” as you shuffle across. The unique experience will have you pondering the science behind it, and its charming unlikelihood.

Sailboats in the harbor of Manchester-By-The-Sea, Massachusetts.

2. Sail Away

You can sit and watch the water, or you can engage with it and sail away. Sailing Cape Ann gives you views of the shoreline only accessed on the water. Sail by spectacular homes, rugged coastal outcrops, and pristine beaches.

Do you have learning to sail a boat on your bucket list? Then Frayed Knot Sailing Charters is your answer to taking the first step. They offer individual and group sailing lessons, making your Manchester-by-the-Sea getaway the perfect time to give sailing a try. Alternatively, if you just want to sit back, relax, and enjoy the view, Frayed Knot offers daily sails and overnight charters that include a captain and crew.

Aerial view of Manchester-By-The-Sea, Massachusetts.

3. Explore Coastline Vistas

The beauty of the Cape Ann area should be experienced outdoors, where you can explore the lovely natural wonderland.

The Coolidge Reservation is known for the expansive Ocean Lawn that provides glorious unobstructed ocean views in a peaceful setting. The Coolidge Reservation Trail is an easy two-mile loop that takes you through the reservation and lawn area. Be aware, parking is limited.

Another beautiful outdoor area is Masconomo Park. Perfect for families, it has a baseball field and a playground. You will also find benches that look out over the serene Manchester Harbor. It is a nice spot to enjoy a picnic or an ice cream while watching the boats come and go and the birds bobbing on the water.

4. Take A Sunday Drive

One of the best ways to explore Manchester-by-the-Sea and Cape Ann is to just set out for an old-fashion Sunday drive. Jump on Route 127 and 127A and you will wind through small villages, elaborate bayside neighborhoods, boatyards, beaches, and exquisite water views. Every so often, get out and stretch your legs and explore little neighborhoods, downtowns, and the peaceful natural beachside areas.

Aerial view of the Misery Islands in Massachusetts.

5. Get To The Islands

Misery Islands consist of two islands: Great Misery, which is 83 acres, and Little Misery which is only 4 acres. The islands were once home to a lavish, Golden Age resort that catered to her wealthy, high society visitors.

You can reach the island by wading across the channel at low tide, however, getting back to the mainland after might require a swim. The most practical way to visit the islands is by canoe, kayak, or dinghy. Once there, you can explore the two and a half miles of trails. The quiet respite of the island is punctuated by the roaring waves and sweeping overlooks where rocky shorelines meet the Atlantic Ocean.

Visit North Shore Kayak Outdoor Center to rent a kayak, canoe, or paddleboard. They offer guided tours of Straitsmouth Island and Thacher Island during which your group will paddle to and then hike around the islands. For the more adventurous, try the Thacher Island Overnight Camping experience. This excursion is customizable for your camping adventure.

6. Relive Manchester’s History

The Manchester Historical Museum is the keeper of all the rich history of Manchester-by-the-Sea’s wonderful past. Active in community events and proponents of a lively downtown, the Manchester Historical Museum is a driving force in local celebrations, history, and the community.

Located in the Trask House where visitors can enjoy an extensive collection of mid-19th-century furniture, fine art, and antique toys, the museum is a fun and educational adventure.

The Hammond Castle Museum in Massachusetts.

7. Visit A Magnificent Castle

The Hammond Castle Museum invites you to explore the grounds and view the castle exterior and bell tower as their guest during museum hours. If you would like a guided tour of the museum, they are offered and need to be reserved and paid for online. Led by guides well versed in the Hammond family history, they will take you on a trip back in time. As you explore the castle and it’s gorgeously furnished rooms, you can almost feel the party atmosphere in the elaborately decorated rooms. How much fun it must have been to enjoyed an evening of dining and dancing in this spectacular home.

Tours offered at the castle include a General Museum Guided Tour, A Candlelight Tour, A Spiritualism Tour, and special seasonal tours.

8. Play A 9-Hole Round

You will find some exceptional golf on Cape Ann, however, many courses, including the famed Myopia Hunt Club and the Essex Country Club, are private and require an introduction or membership. You can still get in a few rounds on a decent public course.

The Cape Ann Golf Course is a 9-hole course skirting the edges of Crane’s Beach. Perfect for beginners or a quick intermediate round, you’ll find Cape Ann Golf Course is a beautiful place to spend a few hours outside enjoying the views.

Another charming Cape Ann course is the Rockport Golf Club, a semi-private 9-hole course offering gentle slopes, open fairways, and a doable par 35 round.

Seafood from Cala's Food and Spirits in Manchester-By-The-Sea.

9. Enjoy Fresh Seafood

Enjoying fresh seafood is a highlight when visiting a coastal town. Manchester-by-the-Sea’s dining establishments offer casual meals with a touch of New England coastal flare.

Cala’s Food and Spirits is a local favorite. From the New England Clam Chowder to their Baked Local Haddock, you will be satiated with yummy goodness.

Black Arrow Provisions is the new kid on the block, and they are rocking it. They offer a wide selection of salads and sandwiches in addition to a few perfected entrees. Consider trying the Crab Cakes served with Rosemary Molasses Beans or the Short Ribs with a Mushroom and Pea Risotto.

10. Shopping In Town

The downtown area is home to a few one-of-a-kind shops offering souvenir treasures for your coastal getaway memories.

4 Beach is just what you would want from a coastal gift shop. Unique finds with a country coastal flair. Take a spin through the shop, and you’ll discover wonderful finds.

Manchester by the Book is a lovely shop to while away time browsing titles and carefully selecting your next read. There is something comforting about holding a book and turning the pages as you explore the world.

Pro Tips

Cape Ann is home to four gorgeous coastal communities, Gloucester, Rockport, Essex, and Manchester-by-the-Sea. You can explore two more of Cape Ann’s charming villages with A Trip Up The Coastline of Massachusetts: Boston To Gloucester or our Boston Day Trip: Rockport, Massachusetts.

If you are searching for the perfect quiet escape with unpretentious charm, Manchester-by-the-Sea will welcome you with open arms. This adorable little village is the perfect spot to get away from the crazy 9-to-5 and relax in the slow, rejuvenating vibe. Cape Ann is the ultimate casually luxurious seaside village where you can enjoy an extra special getaway weekend.