Walks & Hikes, Gloucester

Nobody here but us boulders: bagging Cape Ann’s highest peak

WHAT:A lightly-trafficked trail up 270-foot-high Mount Ann and around a scenic pond
WHY:Enjoy water views and modesty challenging terrain while trekking to a rocky 'summit'

I’m always surprised to find unique destinations just a few minutes away from a main highway, but that’s exactly what I discovered recently when I decided to find Mount Ann and climb it. Located in West Gloucester, Mount Ann’s heady claim to fame is its altitude – a grand total of 270 feet above sea level. Hidden away just south of Route 128, this roughly 4-mile loop trail takes you through woods and streams, and loops around beautiful Dykes Pond, part of Gloucester’s municipal water supply. 

Access to the trailhead is just 5 minutes away off of Route 128’s exit 53. Diving east on Route 133, look for Laurel Street on your right. This is a narrow residential road so ‘take ‘er slow’ and look for a turnout and park at the end of the access road to Dykes Pond. Follow the access road to a woods trail that traverses open woodlands before descending to a cove in Dykes Pond. Continuing on the trail, you’ll encounter a Trustees of Reservations sign that welcomes you to Mount Ann Park. Please note that Trustees advises that the Park is inaccessible due to restrictions to the watershed land surrounding Dykes Pond, but locals use the trails respectfully. 

Summiting Mount Ann is, um, anti-climatic. The peak is simply a prominent chunk of granite bedrock that rises above the surrounding forest. Views are best enjoyed when leaves are off the trees. Following the trail west, you’ll descend into a pleasant babbling-brook drainage and cross a footbridge. The trail then leads to a T trail intersection. Here you’ll take a left and follow the trail around the west and south side of the pond past a dam, where you’ll pick up the access road which will take you back to your car.

FUN FACT: In 1968, Mass DPW proposed an additional ‘beltway’ highway around Boston. With the melodious name of The Middle Circumferential Highway, it would have slashed through much of Boston’s North Shore, including the western side of Mount Ann Park. Thankfully cooler heads prevailed and the highway plan was shelved – yikes!


Marshall’s Farm Stand
144 Concord St, Gloucester | 978-283-2168
Flowers, plants and veggies, just around the corner from the trail

84 Causeway St, Gloucester | 978-281-0415
Hugely popular seafood restaurant on the marsh

Causeway Restaurant
78 Essex Ave, Gloucester MA | 978-281-5256
A local legend, huge portions of delicious seafood