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Best Cape Ann Things to Do (and a 1 Day Itinerary)

Just a short drive from Boston, Cape Ann, MA is brimming with New England tradition with cute seacoast villages, tucked away sandy beaches and enough New England charm to keep you coming back.

This 1 day road trip itinerary around Cape Ann, MA hits the highlights including the best Cape Ann things to do, but you can easily spend more time here, and no matter what time of year you visit, you’ll find plenty to do for a weekend or even a week.

When to Visit Cape Ann, MA

If you want the best weather, visit Cape Ann, MA in the summer months – July and August is prime beach weather but you will also face the crowds, especially on the weekends. The charm of these towns is that they are small and quaint, but you will also find trouble parking and even driving around on these busy weekends. If you can, try to come in June or Sept and Oct to get the best weather when it’s a little less crowded. The hydrangeas bloom in late June if you are hoping to see the gardens in bloom.

Like many towns in New England, visiting during December gives you a chance to see these towns in all their holiday glory. The photos for this itinerary were taken in mid-November on a warm day and we loved exploring these places during the quiet season.

Getting Around Cape Ann

Cape Ann is a small Peninsula jutting out into the Atlantic Ocean northeast of Boston, MA. You will need a car for this itinerary. There are several ways to add on to this itinerary, simply by spending extra time in any of the locations described, or by visiting Salem, Marblehead, or heading North to Newburyport, NH and ME. Since the Cape Ann Peninsula is relatively small, you can drive around it easily in one day. This itinerary includes some easy walking as well, but you can easily adjust these distances if needed.

Cape Ann Things to Do

Below you will find the itinerary we took during our day in Cape Ann and a list of some of the best Cape Ann Things to Do.

Start at Manchester By the Sea

Start your day at Manchester by the Sea. This cute town is the home of the famous film by the same name. Stop by the Laughing Gull Café to get you morning cup of coffee, take a stroll around the harbor, and then hop in your car and drive east on route 127. This road follows the coast and you can glimpse some amazing homes along this stretch of road.

As you drive East, make a short stop at Black Beach, Kettle Cove or explore the Coolidge Reservation for a short walk. The well protected harbor of Kettle Cove offers the perfect respite for boats.

Cape Ann Things to do
Cape Ann Things to do: Manchester by the Sea
Black Beach, Kettle Cove

From here take Herperus Ave for a short visit to Rafe’s Chasm. This short walk takes you out on the rocky coastline for gorgeous views of the water and the classic rocky shoreline. The path was a little muddy when we we visited and there are only a few parking spots, but this little gem is a fun place to visit slightly off the beaten path. We saw people fishing and picnicking here and loved watching the waves crash in on the rocks even on a calm day.

Exploring the Rocky Shoreline at Rafe’s Chasm, Cape Ann, MA

Visit Hammond Castle

Hammond Castle was built in 1926 by inventor John Hays Hammond Jr. This medieval style castle sits right on the coast and was built to hold a private collection of artifacts. You can explore both inside and outside and they have a cute store We loved the views of the ocean and the unique building.

Explore Gloucester

You can’t visit Cape Ann without a visit to the Fisherman’s Memorial in Gloucester. Once you leave Hammond Castle, drive along the shoreline to Gloucester. Gloucester is a good size down with a healthy downtown and plenty of places to stop for lunch. You can get excellent seafood, right on the water or up one street. We grabbed sandwiches as Bishco. Gloucester has a wonderful waterfront walk and you can get out and explore. Make sure you see Gloucester Fisherman’s Memorial. There are also wonderful things to do in Gloucester, including taking a sail, shopping, going on a whale watch, or visiting a beach.

As you leave town, you have the option to drive out to the Eastern Point Light and then you will have your choice of beaches. Stop at one of the beaches for a walk or sunbathing. If you’re brave, take a dip in the chilly waters.

Explore Good Harbor Beach near Gloucester

Stop in Rockport

Rockport is a salty little town on the tip of Cape Ann with incredible New England Charm. This was one of those gems that I didn’t fully appreciate until we took a walk. We managed to get there near the end of a November day and loved walking along Bearskin Neck and popping in some of the fun shops here. This can get VERY crowded in the summer, so make sure you plan extra time if you’re visiting in the warm months.

The jewel of Rockport is the view across the harbor with the lobster pots, stacked traps, piers, boats and famous red fishing shack. This is still a working harbor and the family owned lobster boats give a sense of stepping back in time.

Halibut Point State Park

Jutting out on the ocean at the end of the Cape Ann sits Halibut Point State Park. This old quarry site has excellent walking trails and stunning views of the coast looking north. The old quarry site makes a beautiful photo looking out at the ocean and if you walk out to the point you will find a large granite rectangle with a large hole.

Halibut Point State Park

You’re almost done your day, but there is plenty to enjoy on the drive back towards Gloucester. There are several other excellent beaches to stop at including Plum Cover Beach and Wingaersheek Beach. We loved all the little bodies of water along this ride and it felt like we were chasing the sunset. If you are heading off, it’s time to leave the Peninsula, but if you are staying for dinner or the night you can find dinner back in Gloucester or head into Essex for a meal.

Wow – that was a lot to squeeze into one day, but we hope you enjoyed it as much as we did.

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