Experience the beauty and charm of New England

Check Availability

6 Beautiful Cape Ann Hikes

6 Beautiful Hikes on Cape Ann

You heard it here first—40 miles north of Boston, you’ll find a series of breathtaking hikes.

They’re nestled right here on Cape Ann.

Our destination is known for so much more than its stretch of serene beaches, the golden hour light you can’t help but photograph, and the historic inns and shops adorning our seaside community. (Don’t even get us started on the mouthwatering dining here in Rockport and the surrounding area.)

No, Cape Ann is also celebrated for its network of stunning hiking trails. So leave the Peloton at home (you wouldn’t want to pack it anyway), and get your sweat on by experiencing our best-in-class woodland paths, boulder-strewn trails, and oceanfront promenades.

Searching for natural beauty right here in Massachusetts? You have one thousand percent come to the right place. Keep on reading to learn more about six fantastic Cape Ann Hikes and, trust us, we are really just scratching the surface! 

1. Ravenswood Park| Gloucester, MA

Distance: 2.3 miles for the loop trail, 10 miles total
Time: Approx. 1 hour and 5 minutes

This loop trail features striking views, beautiful wildflowers, and outdoor recreation for all skill levels. The park itself includes 600 acres of natural beauty, offering a meditative experience for those looking to break a sweat and enjoy the local scenery. The park was even home to a legendary hermit, Mason Walton, in the late 19th century and there is still a plaque in the park to honor “The Hermit of Ravenswood.” You can learn more about Mason Walton here

Ravenswood Park Gloucester MA

The park’s 10-mile network of trails—including but not limited to the above loop—offers a perfect daytime experience no matter the season. Snow-covered hemlocks stun in winter, while the fragrance of spring will captivate even the most reluctant hikers. In summer, meanwhile, visitors will find comfort in the park’s namesake shade, and the burst of autumn colors are bound to captivate.

Hikers who refuge at Ravenswood Park can tailor their excursion to their current fitness level. Ample signage and well-marked trail crossings will keep you on track. Here is a helpful link to a trail map of the park

Ravenswood really is an incredible place that is perfect for quiet contemplation or even a nice peaceful run.  When you venture into the woods you feel more like you are in the woods in northern NH than just a short jaunt from the Gloucester coastline. It’s one of the features of Cape Ann that we absolutely love. 


2. Halibut Point | Rockport, MA

Distance: 1.6 miles for the loop trail
Time: Approx. 45 minutes

Find serenity with the sound of crashing waves, and experience the beauty of Cape Ann by visiting Halibut Point State Park. The park’s loop trail is tucked between land and water, located at the very edge of Gloucester—with wildflowers and plenty of opportunity for relaxation.

The historical interpretive trail is tucked between the State Park and the Babson Farm Quarry. Hikers will enter the the forest and approach a 60-foot-deep quarry before reaching the Atlantic. On a clear day, views of Mount Agamenticus—located in Maine about 40 miles away—are bound to stun.

And history buffs, listen up! Rocky ledges, enticing tide pools, and ample trails offer a seamless introduction to the park’s role in World War II and in the granite industry. There’s truly something for everyone here.


3. The Headlands | Rockport

Distance: 0.1 miles
Time: Approx. 5 minutes

A short respite ideal for all skill levels, the Headlands are well-hidden on a downtown Rockport side street. Know as “the overlook capital of Cape Ann,” this pretty lookout is a short walk from Bearskin Neck and an ideal place to sit back and rejuvenate.

Cape Ann Hikes - The Headlands

You’ll want to start your walk at Dock Square before moving up Mt. Pleasant Street and taking a left onto Atlantic. Approach the bend in the road, and simply follow the sign marked “Way to Headlands.” The short, flat trail is a hit for kids and travelers looking for an easier hike with stunning views.

In the colder months, this is a fantastic spot to get a closer look at our feathered friends that visit from the great white north.

Getting out the Headlands is a fairly easy endeavor. All it takes is a few minutes to cross Rockport’s namesake rugged boulders and enjoy the rocky outcroppings, crystal-clear tide pools, and wondrous northern Cape Ann coastline. Don’t forget to sneak a peek to the south for views of the Straitsmouth Island lighthouse.

If you are looking for a longer walk, you exit the back side of the trail and head down toward Old Garden Beach. There are benches and picnic tables that provide a great place to relax and take in the beauty of the surroundings or, if you prefer, you can take a refreshing dip in the Atlantic.  It’s a beautiful area of Rockport that is a little more peaceful than the bustling downtown. 


4. Mount Ann Park | Gloucester, MA

Distance: 1.5 miles
Time: Approx. 45 minutes

Picture this: a hilly trail, lovely and forested, shrouded in beautiful white pine, maple, oak, birch, and hemlock. The Mount Ann Park loop trail offers all of this and more, enticing hikers to take a leisurely stroll. Passing pretty Dykes Pond, the hike leads to a smooth-topped granite summit overlooking Cape Ann before guiding you back to your car.

Mount Ann Park Gloucester MA 

The park itself has been a Gloucester staple for quite some time now—and it’s steeped in captivating history. The brothers of celebrated naturalist Henry David Minot, who penned The Land Birds and Game Birds of New England as a teenager in 1876, donated the land in his memory.


5. Rafe’s Chasm | Gloucester, MA

Distance: 0.2 miles to clifftop views, 0.9 miles to the chasm
Time: Approx. 20 minutes

Located at 138 Hesperus Avenue in Gloucester’s Magnolia neighborhood, this lovely seaside walk is just 7.6 miles from our Rockport, MA hotel. Rafe’s Chasm features a small parking lot where visitors can seamlessly enter the trail. Signage and a trailhead bulletin board will keep you oriented en route to the oceanfront outlook.

Rafe's Chasm

The hike is named for Rafe’s Chasm Park, a 10-acre parcel of land told to the City of Gloucester for $1 in 1959. The trail itself is flat, winding, and wooded. While the initial section is quite easy, winding just 0.2 miles to the ocean (where clifftop views will take your breath away), reaching the actual chasm isn’t quite so easy.

So, proceed with caution after the initial overlook. You’ll need to climb over a number of rocks that might be slippery with water, ice, or sea debris depending on the time of year. We would recommend skipping this hike if you have mobility challenges and leaving the pups behind for safety.

Agile hikers who make it to the chasm, however, will be rewarded with impressive rock formations—perfect for experienced trekkers and climbers in search of something new.


6. Dogtown Common | Rockport and Gloucester

Distance: 6.1 miles for the loop trail
Time: Approx. 3 hours

Adventurous hikers need look no further than Dogtown Common for a taste of Cape Ann history. Tucked between Rockport and Gloucester, the land surrounding this intricate loop trail was settled by colonists from 1693 through 1830. Rich in natural beauty and vivid lore, there’s nothing like this trail here or anywhere else.

Best Cape Ann Hikes

The rocky woodland landscape provided early settlers with protection from pirates, and other enemies arriving in Gloucester Harbor.  Many of the inhabitants of Dogtown were widowed wives of mariners and soldiers who fought in the Revolutionary War. The women kept dogs for protection which is the root of the Dogtown name. After the Revolutionary War, as inhabitants gradually moved back closer to the coastline, it’s rumored, that many of the dogs were left to roam wild.

Hikers should park off Cherry Street before moving into the forest along the uphill road.

The trail itself crosses the Essex National Heritage area, meandering through a quiet stretch of woods. Perfect for those in search of a bit solitude, hikers who move clockwise along the trail will end their experience with the remarkable Babson Boulders decorating either side of the path—reminiscent of the region’s stone cutting industry from the Great Depression. From there, continue moving through the forest before returning on the Old Gravel Road right along the Babson Reservoir.


Experience Coastal New England & The Best Cape Ann Hikes 

We hope you enjoyed the above summary of the top six hikes on Cape Ann! Why not come witness the natural beauty of Rockport and the surrounding area, and get the daily dose of nature you’ve been craving during your stay? You will absolutely want to experience the natural beauty of our coastal enclave.

If you are looking for maps for Cape Ann hikes, the Town of Rockport website has compiled some downloadable PDF’s for popular hikes. In addition, The Trustees of Reservations website is a fantastic resource with a wealth of information about local trails. 

If you have questions about the top hikes on Cape Ann or any other aspects of your trip, our team here at Addison Choate would be more than happy to guide you through your options. From dining to shopping, and from sailing to hiking, we’ll help you curate the experience of a lifetime.

Please don’t hesitate to contact us with questions or for more information.

Check Availability