We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Gloucester Biking Loop

Take a loop ride around the coast of Gloucester by car or bike to enjoy the coastal community life.
Difficulty: Moderate
Length: 30 miles
Duration: Half day
Family Friendly

Overview:  This is a 25-30 mile loop around Gloucester, Rockport and Anniquam. I've included a bunch of great spots that you should bike by and ... more »

Tips:  Follow Route 128 north from Boston to 127 entering Gloucester then start on the beach on Western Ave near the Fisherman's Wives... more »

Take this guide with you!

Save to mobile
Get this guide & thousands of others on your mobile phone
EveryTrail guides are created by travelers like you.
  1. 1. Download the EveryTrail app from the App Store
  2. 2. Search for the Gloucester Biking Loop guide
  3. 3. Enjoy your self-guided tour
Get the app

Points of Interest

1. Fisherman's Wives Memorial

Look for the crew members of the Andrea Gail which lost their lives in a massive storm portrayed in the movie "The Perfect Storm" and book by Sebastian Junger. Also, before you leave this area, make sure you check out my guide for Stage Fort Park just to the south on 127.

A very cool lighthouse to check out at the very southern end of Gloucester.

3. Rocky Shoreline Views

Along this stretch of road you will be right on the water with great views and terrific smells of the ocean nearby.

This is a very cool beach with an island that you can walk to at low tide. Make sure to check out my other guide for this beach.

5. Rockport & Bear Skin Neck

This is a must stop on this ride to check out all the cool shops. You'll even find some local fisherman selling some really great and inexpensive food. My favorites were the shrimp cocktail and smoked salmon at the Ray Moore Lobster Co. Hopefully it is still there and the 2008 crash didn't harm it!

6. First Settler Tercentenary Sign

A sign about the first settler family of Rockport. For more information on Tercentenary signs like this throughout Massachusetts check out the link section of this guide.

I have another guide for this park. Make sure to check it out. This was an old quarry and now it has some really neat trails and a rocky area to sit on near the coast. It's a nice place to relax halfway through your ride.


This cove is absolutely perfect to watch a sunset in.

9. Annisquam Yacht Club

Yeah... you need to have money to belong to this place. The closest I got was a picture of it :)

10. Bridgewater Street over Lobster Cove

You'll see a lot of lobster boats and sailboats in Lobster Cove as you cross this wooden bridge.

11. Washington Street & Goose Cove

Back on 127 you are now crossing over Goose Cove. Keep following Washington Street all the way back to Western Ave and your car.