One corner of Massachusetts we enjoy is the Cape Ann region, on the North Shore. There are some beautiful drives that you can do in the area (or if you can’t visit, “The Perfect Storm” movie offers a glimpse). In this particular case, we did a loop between Gloucester and Rockport by bicycle, though we totally recommend driving it as well.

When driving this route, you will quickly find that there aren’t a ton of pullouts, so if you want to stop for pictures, a bicycle ride may be a great alternative! Note that most of this route is on a fairly narrow road that is shared with cars – as opposed to a peaceful bike path – so consider your comfort level with this before you go.

The Logistics

The Loop

Distance: about 20 miles, dependent on detours you choose!

Highlights:

• Waterfront in Gloucester, including the Gloucester Fisherman’s Memorial and possibly Stage Fort Park
• Beaches: Good Harbor Beach, Pebble Beach, Front Beach, Plum Cove Beach
• Lobster Rolls at Surfside Subs
• Downtown Rockport
• Riverdale Civil War Memorial and other stops on Gloucester’s War Memorial Trail

Getting There

By Car: Since we were bringing our own bikes, we drove to Gloucester and parked in an inexpensive lot close to the Gloucester Commuter Rail station and further away from the water. There are quite a few metered parking spots close to the water, but the city of Gloucester also has a map of all the parking lots.

By Commuter Rail: The commuter rail stops at both Gloucester and Rockport .

Bicycle Rentals

There is currently a shortage of bike rentals in the area (several shops have closed), so make sure you call ahead to make sure there will be a bike waiting for you! We brought our own bikes so don’t have experience renting there.

The Bike Ride

You can start anywhere on the loop, but if you start in Gloucester, you may want to stop by either Stage Fort Park, the Fisherman’s Memorial, or see the drawbridge. Since we had already done a walking day trip on the Gloucester waterfront the year before, we didn’t spend a lot of time here and these pictures are from that trip:

Continuing down the coastline, we encountered some nice views of Good Harbor Beach.

The rocky cliffs toward Pebble Beach and Rockport is an area that’s a little harder to stop at with a bicycle rather than a car.

Biking this route allowed us to stop where we wanted!

Deciding that our lunch preference was for somewhere that we didn’t have to worry about locking up our bikes, when we came to Surfside Subs and saw both picnic tables and a sign advertising Lobster Rolls, we knew we had found our stop! The lobster rolls were delicious and Jeremy thoroughly enjoyed his “small” ice cream cone!

Back on our bikes, we continued to enjoy the scenery until we reached Rockport. This New England coastal town was quite cute, although our pictures don’t do it justice. There was a shopping and boating harbor area.

At the end of the town, there are some great views of the harbor, plus a few spots to lock your bike.

From Rockport, we continued on past Front Beach, around the northern tip of the peninsula, and past Plum Cove Beach, until we came to this Civil War Memorial near Washington Street and Hodgkins Street.

I was a little freaked out biking on the rotary, but that’s somtimes part of being on the road in Massachusetts.

Shortly afterwards, we came back to our car that we had parked in a lot near the Gloucester Commuter Rail Station.

What a nice way to enjoy Gloucester and Rockport! If you travel to Massachusetts, consider a day trip to this delightful area.

Keep reading our travel blog to see how we explore by bicycle: