Cape Ann Loop

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A roughly 40-mile loop around the coastline of Rockport and Gloucester with beautiful ocean views.

Written by

Cody Grodzki


40.0 miles

Destination Distance From Downtown

26.7 miles


4 of 5 diamonds

Time To Complete

3 hours

2-4 hours


Spring, Summer, and Fall

Best in Summer.

Dog Friendly


Fees Permits


Topographical Map

Cape Ann Loop Map

Land Website

Cape Ann Loop



A beautiful loop that takes you for a wonderful ride around the coastline of a couple of Massachusetts' more well-known, but less-frequented cities. Located around Rockport and Gloucester, (pronounced “Glaw-stah”; the same Gloucester where the film "The Perfect Storm” took place) this is great chance to get a real taste of the North Shore/ Cape Ann area, and at just under an hour drive from Boston, is a completely reasonable day trip.

What Makes It Great

Cycling along the loops of Rt. 127 and Rt. 127A will have grant you a beautiful, unimpeded view of the Atlantic ocean throughout your journey, as well as take you through some areas to grab a snack or lunch should you choose. Not a particularly busy loop, but there can be traffic, especially in the warmer months, so be sure to keep a heads up for cars who may also be enjoying the same views as you.

Who is Going to Love It

Cyclists looking for some distance are going to love the options that this destination offers. There are three separate possible loops, all originating in Gloucester.

Clocking in at 10 miles, the shortest ride is the Route 127A to Route 127 route- basically, a loop ride to Rockport and back to Gloucester.

At 14 miles, the next ride up in terms of distance is the Route 127 loop. This ride also takes you to Rockport, but then up swoops up to Halibut Point State Park and down all the way until Route 127 becomes Washington Street, eventually landing you back in Gloucester.

Last but not least, the 16 mile loop. Take Route 127A to Rockport, but instead of heading south back to Gloucester as in the first loop, continue onward towards Halibut Point State Park. Once there, continue to follow this loop all the way back to Washington Street and then the center of Gloucester.

Directions, Parking, & Regulations

Getting to Gloucester may require a bit of drive out of the city, but once you hit the coast, you’ll be happy that you chose this destination. Just be sure to leave earlier in the day, so that you avoid the treacherous afternoon commute to the North Shore. The 93/95 split can back up traffic to a point where it will literally take 30 minutes to travel 1 mile.

From Boston, follow Route 93 North to Route 95 North and then to Route 128 North. From there take the first exit around the rotary (Washington Street) and follow this to Prospect Street. You will now be at the center of town. Look for public parking and get ready to ride!


Cape Ann Loop

9 Dale Ave
Gloucester, MA, 01931
42.614076, -70.662781

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