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Walking Trails and Scenic Hikes Around Cape Ann

Hiking trails around Cape Ann  - Ravenswood - Gloucester MA
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Things to Do on Cape Ann

Cape Ann's unique location means that the area has a diversity of scenery, from sandy beaches and rocky shorelines to salt mashes and hilly woodlands. Luckily for those who wish to enjoy the natural beauty of Cape Ann, there are many public parks and conservation areas that offer trails for walking, hiking, or biking in addition to incredible scenic views.

Here are some of the area's best spots for hiking trails, nature walks, and family outings.

Halibut Point State Park - Rockport

Located at the very tip of Cape Ann, Halibut Point State Park is the site of the old Rockport Granite Company's Babson Farm Quarry. Set against a stunning ocean backdrop, walking trails circle the quarry and also lead down to the rocky shore below. Gaze at the clouds reflected in the quarry's glassy surface or explore tide pools and collect shells, sea glass or interesting stones shaped by the sea.

Learn more about visiting Halibut Point

Tompson Street Reservation - Gloucester

Thomson Street Reservation - Gloucester MA

Explore some higher elevations in one of the Essex Greenbelt’s largest reservations. Hike up Sunset Mountain and Eagle Rock at Tompson Street Reservation to find stunning views of Gloucester Harbor and Ipswich Bay, taking your pick of several miles of hiking trails. ​The reservation is also the original site of the Second Parish Church, established in 1716 so that West Gloucester residents did not have undertake the arduous journey to the First Parish Church in downtown Gloucester.  

Learn more about visiting Tompson Street Reservation

Coolidge Reservation - Manchester-by-the-Sea

Coolidge Reservation packs a lot of terrain into a relatively small area, just 66 acres. Once the site of Georgian-style mansion and large estate, Coolidge Reservation now offers woodland trails, grassy expanses, a freshwater pond, a rocky shore, and incredible ocean views. On clear days, you'll even see the Boston skyline in the distance. 

Learn more about visiting Coolidge Reservation

Ravenswood Park - Gloucester

Experience the serenity and beauty of nature in Ravenswood Park. With walking and hiking trails throughout its 600 acres, Ravenswood is a favorite spot for hikers, explorers, nature lovers, and artists. Wide "carriage paths" allow for groups to easily walk together, while the hiking trails offer a more challenging terrain. Make your way to the summit of the Ledge Hill Trail for views of Gloucester Harbor.

Learn more about visiting Ravenswood Park

Dogtown Common - Gloucester

Dogtown Common - Gloucester MA

Dogtown Common is widely regarded as one of New England’s most famous abandoned settlements, and has been featured in books such as The Last Days of Dogtown by author Anita Diamant. Covering a 3,600-acre stretch of forested land in the heart of Cape Ann, Dogtown is full of natural beauty, including ancient glacier-formed rock formations and two reservoirs. While walking the trails, you'll want to pause and contemplate the inspirational sentiments carved into numerous boulders, carved by local quarry workers during the Great Depression.

Learn more about visiting Dogtown Common

Allyn Cox Reservation - Essex

Once the site of a farm, the Allyn Cox Reservation encompasses open fields and salt marsh, sitting at the edge of a tidal estuary. The trails provide excellent opportunities for birdwatching: osprey, herons, egrets and kingfishers can be seen in the salt marsh while birds such as bobolinks, meadowlarks, and bluebirds live in the old farm fields. This is also a popular spot for plein air painters, with scenic views in every season.

Learn more about visiting the Allyn Cox Reservation

Warren Weld Woodland - Essex

The Warren Weld Woodland is a subsection of the larger Manchester-Essex Woods, covering 106 acres. A variety of flora and fauna can be seen in the woods and in the vernal ponds that are home to a variety of frogs, spotted turtles, and other amphibians. Birdwatchers will appreciate the variety in the bird population.

Learn more about visiting the Warren Weld Woodland

Turn Your Weekend Hike into a Weekend Getaway

Atlantic Vacation Homes offers a wide variety of vacation rental homes across Cape Ann that would be perfect for your Cape Ann getaway. To book your accommodations, simply view available vacation rentals and enter your desired dates to get a quote. You can also call toll-free at (855) 853-9143 to speak with a Guest Experience Specialist.


Atlantic Vacation Homes Atlantic Vacation Homes is the premier vacation home rental & real estate company on Boston's North Shore, with over 30 years of creating dream vacations for our guests. Situated a little more than a half-hour’s drive from downtown Boston, the North Shore is the ideal spot for an east coast vacation. We specialize in coastal vacation rentals for families, large groups, and anyone else who wants a beach vacation in Massachusetts.