Cape Ann is a beautiful stretch of coastline in Massachusetts, and is made up of four gorgeous New England towns: Rockport, Manchester-by-the-Sea, Gloucester and Essex. Even though it’s a small region at just 58 square miles, that’s actually one of the best things about it. By staying anywhere in Cape Ann, you can easily visit all four towns, and take in all the beautiful and unique sites this little Cape has to offer. If you’re wondering what to do in Cape Ann, MA, I have some awesome suggestions for you, so just keep reading!
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What To Do on Cape Ann, MA
Each of the seaside towns that make up Cape Ann have amazing sites to take in, delicious restaurants, beautiful storefronts and loads of character. Let’s jump into the absolute best things to do in Cape Ann.
1. Visit the Most Painted Building in the Country
Who knew that in the small little coastal town of Rockport, MA, you could find what is said to be the most painted building in all of the United States? But it’s absolutely true. Motif 1 is a simple red fisherman’s shack that stands proudly in Bradley Wharf, and while it’s had many purposes over the years since it was first built in the 1840’s, it’s since become a time capsule, of sorts, for the town. Community members have contributed artwork and old fishing gear to the building, and if you take a peek inside, you can see all the treasures the town has donated that are stored inside.
When visiting Motif 1, you’ll likely see artists stationed with their easels creating their own take on the building. Witnessing how much this little shack inspires so many people is such a great feeling to take in.
Fun Fact: This building was also used in a few movies. The Proposal with Sandra Bullock, Betty White and Ryan Reynolds was filmed in Rockport, with an entire scene at Motif 1. The Love Letter, with Kate Capshaw, Ellen DeGeneres, Tom Everett Scott and Tom Selleck also used a lot of Rockport’s landscapes in the movie, including clips of Motif 1.
2. Walk, Shop & Dine on Bearskin Neck in Rockport
After visiting Motif 1, Bearskin Neck is just a few steps away, and is one of the most charming little areas I’ve ever visited in New England. Bearskin Neck is a little shopping, dining and art district that begins at Dock Square in Rockport, and ends at at a beautiful breakwater in Rockport Harbor.
You won’t find any franchises here, and every store is locally owned, with the shop owners taking great pride in the community. This is absolutely one of my all-time favorite things to do on Cape Ann, and I suggest taking an afternoon to wander the streets, admire and visit all the colorful storefronts, grab an ice cream cone, and end your slow meander at the breakwater where you can grab a spot for yourself to watch the fisherman’s boats come and go from the harbor.
My Can’t-Miss Stops on Bearskin Neck:
- The Ice Cream Store, which is probably the most picturesque ice cream shack you’ll ever see.
- Roy Moore Lobster Company for fresh seafood.
- The Pewter Shop for locally made and one-of-a-kind jewelry. You can even get Motif 1 jewelry here.
- The Rockport Candle Company hand-pours all their candles on-site, and each fragrance is inspired by a seaside memory.
Tip: While Bearskin Neck is my favorite area of Rockport, there’s so much more to this beautiful little town. Be sure to walk the opposite direction (away from Bearskin Neck) on Main Street for more store fronts, restaurants and amazing art galleries. Rockport’s community is hugely supportive of the local artist community, so you could spend the entire afternoon visiting just the art galleries.
Click here for more amazing things to do in Rockport!
3. Hear Sand “Sing” at Singing Beach in Manchester-By-The-Sea
It’s said that if you move your feet in just the right way along the sands of Singing Beach in Manchester-by-the-Sea, it will sing for you. So, of course, I had to to see if it was true. Now, it doesn’t actually sound like singing, but when you kind of scuff your feet into the sand at this beach, it does make a unique sound.
There doesn’t seem to be a scientific explanation for why it does this only at particular beaches around the world, but there does seems to be consensus that when sand grains are of a certain size, and are free from as much pollution and dust as possible, the sound is created by the special-sized grains rubbing against their bottom layer. They is supposedly how clean the sand is, and you can find that special sand here!
Tip: You’re more likely to hear the “singing” sound on dry sand, so try and scuff your feet further from the shoreline.
Even if the singing sands don’t appeal to you, the actual beach itself is absolutely beautiful. It’s just under a half mile of gorgeous, pristine sandy shoreline and beautiful turquoise water. The beach lot does fill up quickly in the summer, so it’s best to arrive as early as possible, especially on weekends.
Parking: Parking at Singing Beach is a bit tricky, and there are a lot of rules, depending on the time of year. I suggest you visit the town’s beach website for more information before your visit.
3. Take a Tour on a Schooner Built By The Owner Himself
The Schooner Ardelle offers both public and private tours along Gloucester Harbor beginning in early May through mid-October, weather depending. What’s incredibly special about this particular tour is that the schooner was built by the owner and captain himself, Harold Burnham, and he constructed Ardelle using parts from another schooner, and trees rejected by local arborists and tree companies, so that it was entirely made from recycled materials. On top of that, local friends and neighbors volunteered their own personal time to help Harold finish construction of the boat, making this vessel a true pillar of the community.
Public tours on Ardelle are two hours, and are offered at different times through weekdays and weekends. Reservations can easily be made online through Schooner Ardelle’s website. The vessel can also be reserved for private groups and charters. During tours on Ardelle, guests have the opportunity to be hands-on and assist the crew in the hoisting of the sails, or you can sit back and relax, and take in the beautiful views of the harbor.
5. Visit Eastern Point Lighthouse
This beautiful lighthouse is located in Gloucester, and is unique because of the amazing granite breakwater rock jetty that’s accessible from the lighthouse grounds. Eastern Point Lighthouse was first built in 1832, and was re-built two more times, and the version standing today was built in 1890. The immediate lighthouse grounds (designated by a fence) as well as the interior of the lighthouse are not open to the public, but you are able to explore the grounds of the lighthouse outside of the fenced-in area, which makes for some amazing views.
The breakwater rock jetty outside of the lighthouse is just over a half-mile long, and walking the whole thing and back will not only offer you spectacular views of the lighthouse, but also of the harbor. As much as I love lighthouses, I had just as much fun on the jetty during my visit, and it’s definitely something to consider when planning out what to do on Cape Ann, MA.
Tip: As you approach Eastern Point Lighthouse in your car on Eastern Point Boulevard, you’ll begin to see “Private Road” signs. Public access to the lighthouse is allowed, so as long as you continue to drive directly to the lighthouse, you can ignore those signs. There is a small parking area at the lighthouse. The grounds are open from 8a-8p every day, and there is a gate at the entrance that prohibits cars from pulling into the parking area when the grounds are closed, so be sure to plan accordingly.
6. Drive The Essex Coastal Scenic Byway
This scenic rodeway spans over 90 miles along the Massachusetts coastline, and begins in Lynn, MA and ends in Salisbury, MA. But, smack dab in the middle of this byway is a section that will allow you to drive through all of Cape Ann.
You can either start in Manchester-by-the-Sea, drive though Gloucester, around Rockport and end in Essex, or do the reverse. This route one-way is less than 90 mins without stops, so for a perfect day of leisurely driving, plenty of stops to make along the way for a bite to eat, beaches, Main Streets for shopping, or beautiful overlooks, this is a great way to see all of Cape Ann in one full day.
7. Explore Halibut Point State Park in Rockport
This park in a treasure trove for nature lovers, and offers incredible opportunities for bird watching, wildflower tours, tide pool ecological observation, and of course, stunning views of the Atlantic at the park’s Scenic Vista lookout. There are plenty of easy hikes in the park that allow you to really connect with nature, so this is a great family-friendly experience.
Pricing: The park is free to enter, but there is a charge for parking between Memorial Day and Columbus Day. Massachusetts residents pay $5 to park, and out-of-state residents pay $20 to park. This is per vehicle, not per person.
8. Visit Hammond Castle
How often can you say that you visited a castle built by a scientist and inventor in the 1920s that looks like it’s from the medieval time period in Europe, but is actually in Massachusetts? Well, if you visit Hammond Castle in Gloucester, you’ll be able to! This castle sits on a bluff overlooking the Atlantic, and has stunning grounds and architecture, as well as a fascinating history. The castle offers both guided and self-guided tours, and is most definitely worth considering when planning what to do on Cape Ann.
Pricing: $18 per adult, $15 per senior, children 5-10 are $10, and children 4 and under are free (but still require a ticket for entry). Tickets for guided tours can be purchased in advance online, but self-guided tour tickets can only be purchased in-person at the museum shop. The castle is closed during the winter season, so plan appropriately.
9. Eat Fried Clams Where They Were Invented at Woodman’s
Fried clams were invented right here in Cape Ann! During your trip, you can actually eat fried clams at the restaurant where they were first created, Woodman’s of Essex. This popular seafood shack dish was first attempted because a local fisherman told a concession stand owner that he should try to fry up his bucket of clams since business was so slow. So, the owners of the stand, husband and wife Chubby and Bessie Woodman, gave it a try. Within 24 hours, they were sold out. They even documented the day on the back of their marriage certificate, along with the dates their two sons were born.
Today, Woodman’s of Essex not only serves up these famed fried clams, but also everything else you would expect from a New England seafood shack including lobster rolls, clam chowder, lobster dinners, fried seafood platters and ice cream. The restaurant offers both indoor and outdoor seating, and the outdoor seating is the traditional seafood shack picnic tables overlooking the water.
10. Visit One of The Many Beaches
Since this region is bordered by the Atlantic, chances are you’ll want to visit a beach when thinking about what to do on Cape Ann. While I’ve already touched on Singing Beach, there are over 20 beaches in the area, and regardless of the season, it’s definitely worth visiting a few during your stay. Here is a breakdown of the best beaches on Cape Ann.
- Good Harbor Beach in Gloucester is one of the most popular beaches, and for good (pun intended!) reason. It’s a nice sandy beach for walking, and at low tide, offers the option to walk out to Salt Island on a sandbar. The beach is surrounded by sand dunes, and at high tide, the waves will often be great for boogie boarding. Shower and bathroom facilities are on site. Local residents can park with a beach sticker, and all others will pay $25 to park on weekdays, and $30 on weekends and holidays.
- Wingaersheek Beach on Ipswich Bay in Gloucester is another favorite for families because of the shallow, warm water and soft, sandy shore. At low tide, you can also take another sandbar walk for about a quarter mile toward Annisquam Lighthouse. Be sure to check tide schedules before deciding to take the walk. Facilities include showers, bathrooms and a small snack shack. Parking is $20 on weekdays, and $25 on weekends.
- Plum Cove Beach in Gloucester is an amazing sunset location. The waters are calm due to the beach being surrounded by bluffs, making it a great choice for families with younger children, and it’s absolutely necessary to stay until sunset on a clear day. Parking here is more difficult, as it’s entirely reserved for those with town of Gloucester beach parking stickers. It’s recommended if staying nearby, to walk or bike to the beach to avoid having to park. This makes it worth a visit since for that reason, it won’t be crowded.
- Pebble Beach in Rockport is a great beach for exploring and walking. It’s not as popular for swimming since, as you’ve likely guessed, the shoreline is often covered in stones. It makes a great beach for walking, however, because the stones are smooth. This beach is often less crowded than the popular swimming beach, so it makes for a serene and calm experience.
11. Go On A Whale Watching Tour
Cape Ann Whale Watch is so confident that you’ll see a whale on their tour, they actually guarantee it. Their promise to you is if you don’t see any whales during your tour, they offer you free tours for life, so it’s pretty safe to say that you’ll get to see some beautiful whales during your trip.
Cape Ann Whale Watch is unique in that they also offer private whale watches on a smaller boat. For groups up to six people, you can charter a private whale watch tour, which is about 1-2 hours longer than the traditional tour, and also includes a voucher to cash in for one traditional tour at a later date. For families, or a group that want a more customized, personal experience, this is a great way to spend a half day out on the water. They even allow you to bring a cooler on board with snacks, and just ask you don’t bring alcohol or glass on the boat.
Pricing: For traditional tours, the cost is $55 per adult, $50 per senior, $40 per junior (ages 4-16) and $10 for children 3 and younger. Traditional tours are 3-4 hours long. For private whale watch tours, the cost is $500-$600, depending on the size of the group, and lasts 4-5 hours.
Where Is Cape Ann, MA?
Cape Ann is located along the North Shore of Massachusetts and is bordered by the Atlantic Ocean. It’s about a 40-minute drive heading North from Boston to reach the southern-most area of Cape Ann, which is Manchester-By-The-Sea. From Manchester-by-the-Sea, you can then keep driving North along the coast to explore Gloucester and Rockport, and drive further West to visit Essex.
How To Get There
To get to Cape Ann, a car will be necessary, as public transportation isn’t extensive enough to allow you explore this region by bus or train. The closest airport will be Boston Logan International Airport, and it’s best to rent a car directly from the airport, and then drive to Cape Ann.
Depending on where you want to go, the drive from Boston will take anywhere from 40 minutes to 1 hour, depending on traffic getting out of Boston. Manchester-by-the-Sea will the closest destination, taking about 40 minutes to drive from Boston, and Rockport will be the furthest destination from Boston, requiring about an hour.
What Is Cape Ann Known For?
I’ve already touched on how Cape Ann is known as the birth place of the fried clam, as well as the most painted building in the country, Motif 1, but this region is also known for being a huge antiquing destination.
Essex, the smallest town on Cape Ann, is home to over 25 antique stores offering something for everyone. Many of the antique shops themselves are even housed in buildings from the 18th and 19th centuries, making them worth visiting just to see the buildings. Most of the shops are walkable to one another on Main Street, making it easy for a casual afternoon of shopping and lunching. I can sometimes get overwhelmed by antiquing, but Essex makes it so easy, relaxing and enjoyable. I definitely recommend an afternoon of visiting the antique shops in Essex when planning what to do on Cape Ann, MA.
What Is The Difference Between Cape Ann and Cape Cod?
The biggest difference is location. Using Boston as a reference point, they’re in opposite directions. Cape Cod will be south of Boston, and a longer drive from the city (1-2 hours, depending on your destination). Cape Ann is North of Boston, and a quicker drive from the city (less than an hour).
Cape Ann is also smaller than Cape Cod, and more manageable for a quick trip or a weekend getaway. Cape Cod is about 6 times bigger than Cape Ann, and is home to the National Seashore and more pristine, sandy beaches. Cape Ann still has miles of coastline, but it’s known for being more rocky and rugged. Although, there are still some beautiful, sandy beaches in Cape Ann, you’ll just have fewer to choose from than you would on Cape Cod. Both Cape Cod and Cape Ann are located along the coast of the Atlantic Ocean.
Cape Ann tends to have fewer crowds than Cape Cod, especially in peak season, which is July and August.
Both destinations are absolutely gorgeous and worth your time. The deciding factor when debating these two areas for a trip will likely be time. Cape Ann may be a better choice if you only have a few days, or a weekend. Or, if you prefer less crowds and shorter drives. Cape Cod might be a better option of you have more time (a week or more), love sandy beaches, want to cover more ground, swim in big waves and have a more beachy vibe during your stay.
I usually visit Cape Ann is the late Spring and fall seasons, and Cape Cod in the peak summer season to take advantage of the beaches when the water is at its warmest.
Why is it Called Cape Ann?
Cape Ann was named by King Charles I, after his mother, Queen Anne. It had previously been named Cape Tragabigzanda by the explorer and captain John Smith (yep, that John Smith!), the first person to have drawn a map of the region.
Fun Fact: There is a rock formation near Eastern Point Lighthouse called Mother Ann, which is said by locals to be a silhouette of Queen Anne. Some disagree, and say it’s the silhouette of a women lying down. Visit this rock during your excursion to the lighthouse and see which one you think it is!
When Is The Best Time to Visit Cape Ann?
July and August are the most popular months to visit Cape Ann, and they will also be the most crowded. That said, this is time you’ll have the best weather, warmest waters for swimming, and all the shops and restaurants will be open for the season.
If you’re looking to visit with fewer crowds, I suggest June and September, although, these months are becoming more popular now as well. If going swimming isn’t a big priority for you, I would also suggest looking into visiting in May or October/early November. I’ve been to this region in both May and November, and it was very quiet, most restaurants and shops were open, and it was actually nice to explore the sites in cooler weather.
Best Places To Stay
Since all the towns on Cape Ann are a very short drive from one another, I suggest looking in the entire region for a hotel that best suites your needs. It’s important to note that in summer season, it’s hard to find less expensive rates at hotels, and you will likely spend $150 per night minimum if you happen to find a good deal, but more likely in the $200 range. Outside of peak season, you can definitely find better deals.
Here are three of my top suggestions:
Luxury: Beauport Hotel in Gloucester is an ocean-front hotel with a resort feel. Pricing in peak summer season will start at around $350-$400 per night on weekdays and includes a rooftop pool and bar, bicycles to use during your stay, complimentary valet parking and an on-site restaurant.
Moderate/High End: Addison Choate in Rockport. Pricing in peak summer season will be around $250-$350 per night. This boutique hotel offers individually decorate rooms, Smart TV’s, newly renovated rooms with updated marble bathrooms, a full breakfast included in the room rate and free parking. While not located right in the heart of the shops and restaurants in Rockport, it’s a very easy 10-minute walk from the hotel into the center of town.
Budget: Sea Lion Motel in Gloucester. Pricing in peak summer season will be around $170-$190 per night. The motel has an on-site outdoor pool, and is only a mile from a beach. They’ll even provide you with discounted parking passes for beach lots as an added bonus.
Tip: I use Booking.com for almost all my trips. I love that you can search for vacation and apartment rentals, as well as traditional hotels and resorts, all on one website. And the pricing and deals offered are always the best.
Best Places to Eat
It’s so hard to narrow down the best restaurants and seafood shacks because you’ll be able to get fresh seafood and delicious meals almost anywhere on Cape Ann. But I highly suggest you check out these places during your visit.
For a cozy but upscale dinner, I suggest Duckworth’s Bistrot in Gloucester. The interior feels like a comforting New England home, and the menu focuses on fresh seafood and local ingredients. They also have vegetarian options.
I know I’ve already mentioned Roy Moore Lobster Company in Rockport, but it’s worth mentioning again. Amazing lobster rolls and seafood all-around, and the location is Rockport is a little shack full of character. There are almost always lines, which is most definitely a sign that this place is worth the hype. There is picnic table-style seating here, and it’s also BYOB.
For the best breakfast, lunch or brunch, Sugar Magnolias in Gloucester is the place to go. They offer traditional breakfast foods like egg sandwiches, scrambles and omelettes, but the thing to order here are their sweet breakfast offerings like their french toast or pancakes. They also offer soups, sandwiches and salads for lunch.
Lobsta Land in Gloucester is another favorite. It’s a sit-down restaurant with both indoor and outdoor seating, and also has a full bar that serves beer, wine and cocktails. And of course, the food is awesome. This is a great place to go if you’re looking for a seafood shack vibe, but also want a more traditional restaurant experience with table service and drinks.
And of course, I’ve already mentioned Woodman’s of Essex, birthplace of the fried clam, which definitely can’t be missed!
Tip: Many restaurants on Cape Ann are very seasonal, meaning they may not open until Spring, and might close sometime in the fall season. Be sure to check a particular restaurant’s website for more information before making a special trip.
What To Pack For Cape Ann
Cape Ann is a very casual destination, so regardless of the season, I recommend keeping it simple, and of course, checking the forecast a day or two before you leave to gauge chances of rain and average temperatures. New England weather is beautiful, but can be moody and rainy, especially in the spring, so it’s best to be prepared. Below is a guide on things to consider when deciding what to pack for a trip to Cape Ann, in addition to the outfits and essentials you’re already bringing.
- Light jacket, preferably waterproof, or water-resistant, in case of rain
- Umbrella
- Duck boots or wellies for rainy days if the forecast calls for them (duck boots are also great for spring/fall beach walks)
- Sneakers or comfortable sandals for walking on non-rainy days (depending on temperatures)
- Baseball hat to feel like a real New Englander!
- Light layers such as t-shirts under light sweaters or sweatshirts for chillier days
- Sundresses and t-shirts/shorts/jeans for every day on warmer days
- Swimsuits and coverups for beach days
- Beach hat, beach bag and beach flip flops for beach days
- Sunscreen
- Reusable water bottle
That’s a Wrap on What To Do on Cape Ann, MA
That’s everything I have for you on what to do on Cape Ann. I hope you consider this beautiful region for your next adventure because it truly is a stunning destination filled with so many unique experiences, all while offering the perfect coastal New England getaway.
