Fun Bike Rides in Rockport, Massachusetts

I Want To Ride My Bicycle | Bike Rides In Rockport, Massachusetts

On your next visit to Rockport, Massachusetts we recommend that you take some time to enjoy the local scenery while cruising around by bicycle. What better way to enjoy the quaint charm of Rockport, the stunning views of Halibut Point, or the beautiful beaches of Cape Ann than out in the fresh air.

Enjoy exploring this beautiful coastal landscape which we call home on new rental bikes provided by Addison Choate. Not sure on which course to plot? No worries, we have you covered. Here are some fun bike rides in Rockport, Massachusetts to help spark your imagination. However, we all know that the road less traveled is usually the most interesting.

Rockport MA Bicycles

The Ice Cream Store (0.4 Miles)

Is there anything more quintessential New England Summer than taking a bicycle ride down the coast to get your favorite ice cream cone? We submit that there is not! Under ½ mile away from Addison Choate, you can cruise down the Ice Cream Store, a picturesque coastal shack overlooking Sandy Bay.

Enjoy your favorite scoop while meandering down Bearskin Neck or just admiring the history and beauty of Motif #1. Take in a deep breath of that good sea air, pass by the lobster boats in the harbor, and enjoy this time machine back to childhood! It’s definitely one of our favorite bike rides in Rockport Massachusetts. 

Halibut Point Bike Rides

Halibut Point (2.9 Miles)

Just a short ride up the coastline, on Granite Street, you will find Halibut Point. The northernmost point of Rockport, Halibut Point is a 67-acre reserve that was formerly the Babson family quarry. Granite from these quarries paved the roads of major cities like Boston and Philadelphia and even made its way into the Panama Canal!

Check out the old quarry and scuttle across granite rocks on the oceans edge. On a clear day you can see Crane Beach in Ipswich as well as Plum Island and the Isles of Shoals. It’s a great place to meander and take in the beauty of Cape Ann’s coastline.

Bike Rides in Rockport MA

The Lobster Pool (3.0 Miles)

If you’re heading up to Halibut Point, you may want to continue a little bit further down the craggy coastline and hit up the Lobster Pool restaurant. The Lobster Pool is a classic, down home, New England Lobster Shack that has been in Rockport for over 30 years.

Get a nice steamed lobster, fried clams, scallops or oysters and watch the sun go down over Ipswich Bay from the tables out back. It’s a beautiful way to kick off a Summer evening.

A word to the wise, the Lobster Pool is BYOB, so if you’re thinking of imbibing you should come prepared! An easy way to do so is popping into Whistlestop Market on the way up (left right before Dunkin Donuts off 127/Granite Street) and grabbing a bottle of wine or some local craft beer for your journey. 

Bearskin Neck Shopping

Bearskin Neck Shops (0.5 Miles)

Feeling a little retail therapy? Well, we have the perfect bike ride for you! Just grab one of the rental bikes at Addison Choate and cruise on down to the shops of Bearskin Neck.

You can peruse a fantastic variety of Rockport MA shops, art galleries, and some fantastic little boutique clothing and jewelry stores.

Bearksin Neck is a great reminder of times gone by. You will be able to meet the artists and shop owners, who are all very friendly and get a feel for the local culture. If you get hungry, not to worry there are some fantastic Rockport MA Restaurants nearby.

However, it’s almost a rite of passage to get a steamed lobster or lobster roll from Roy Moore’s Lobster shack and take a seat out back overlooking the beautiful scenery of Rockport Harbor.

Stroll all the way end of the neck and scuttle over the jetty rocks which look out toward the Headlands and back toward the harbor. It’s a popular place for a photo op.

Rockport Massachusetts

The Headlands (0.7 Miles)

Take an easy cruise right down Broadway toward Dock Square. At the intersection bear right and head up Mount Pleasant Street. On the left, you will pass by the Hannah Jumper House home to the leader of the temperance movement in Rockport, Massachusetts.

Back in 1856, Jumper led a band of hatchet wielding women through the town which ultimately sowed the seeds of prohibition in Rockport which kept the town dry until 2005.

After passing the Jumper house you can take a left down Atlantic Ave. On your left you will get views of Rockport Harbor and the Sandy Bay Yacht Club. At the end of the road you will come to a trail which will lead you to a rocky outcropping. From here you can get a beautiful view of the harbor and bearskin neck and just sit back, take in the sea breeze and watch the boats sail by.

If you are feeling more adventurous you can meander over to Old Garden beach. There is a public pathway behind some of the homes and you can walk along the small beach and continue on for views of Straitsmouth Island and even twin lights if you continue along Marmion Way.

Rockport Massachusetts

Front Beach (0.3 Miles)

Not looking for a significant excursion, but still want to get your toes in the sand? Cruise on down to Front Beach. You can park you bike, enjoy the beach.

It’s a quaint beach with rocky outcroppings that is well-maintained and rarely crowded. You can walk over the rocks and inspect the tide pools for aquatic life. After getting a quick injection of vitamin sea you can grab a quick bite to eat at Nate’s. They have a delicious breakfast! We think this a great, relaxing Rockport MA bike ride! 

Good Harbor Beach Gloucester MA

Good Harbor Beach (3.3 Miles)

Take a longer cruise out to Gloucester’s popular Good Harbor Beach. Enjoy the salty breeze as you peddle out past Straitsmouth Island and Thatcher Island. You’ll realize biking was the right choice, when you see the full parking lot!

Park your bicycle and enjoy the dunes and marshes surrounding this beautiful beach. The beach is very clean, well maintained, and has some of the best waves on Cape Ann.

Glosta MA

Downtown Gloucester (2 Miles From Good Harbor or 4 Miles from Addison Choate)

If you’re feeling really adventurous you can cruise on down the road a couple miles further and head right into downtown Gloucester. Gloucester is an historic fishing village which still has a deep respect for it’s nautical heritage.
You will bike past the docks and Connolly Seafood, as well as the Crow’s Nest Bar, made famous from the movie the Perfect Storm. Stop off for a pint as you head toward the shops.

Downtown Gloucester has charm in spades. It feels like a classic New England coastal city like Portsmouth, NH or Portland, Maine. There are some great local bookstores, restaurants and unique shops to visit. Dig through vintage records at Mystery Train, find unique clothing at Brass Monkey or find a new favorite cheese at the The Cave. But be sure to remember that you have to save some energy to cruise on back to Rockport.

Fun Bike Rides in Rockport Massachusetts

We hope that you’ve enjoyed our suggestions for fun bike rides in Rockport Massachusetts and that they have sparked your imagination for some other great Cape Ann adventures! We are excited to be offering bikes to guests of our Rockport MA boutique hotel and hope that you will take advantage of them when you visit!