Cape Ann: Day Trip from Boston
I am a New England lover. In fact, I'm pretty sure I was born in the wrong region. I attended college in Boston and lived for two years in New Hampshire, so each fall, we spend one glorious weekend in New England. Last year's trip included a day in Boston and a day on Cape Ann.
Saturday, 10 am:
We departed from Boston and drove to Gloucester (about 1 hour). If you don't have a car, you can also take the Newburyport/Rockportline on the commuter rail from North Station.
Exploring Gloucester:
Our first stop in was Stage Fort Park. We parked at the first lot, walked around the beaches, through the woods, and took in some fresh air. There is a nice lookout point with some benches, as well as some old cannons for the war buffs.
After a visit to the beaches, we passed the famous Fisherman statue, created in 1925, which honors those lost their lives to the sea.
Disclosure: This post includes affiliate links to products and referral links to credit cards that we use. For all affiliates, we earn a small percentage of any purchases. When we share links to credit card applications, if you click on that link and are approved, we will be compensated with points at no additional cost to you. We will never share any products or credit cards that we do not use ourselves.
Next stop was the Cape Ann Museum. During our October visit there was a moving display of portrait photography Jason Grow of WWII Veterans from the North Shore.
After the museum, we walked over to the water to have lunch. We ate at Cape Ann Brewery, which has since closed.
Saturday, 2pm: After a satisfying meal, we drove to Rockport and checked in the Pleasant Street Inn.
Tip: Rockport is a walk-able town, so it makes sense to leave your car in one place for the day.
We spent the afternoon exploring the shops on Bearskin neck. Our day consisted of drinking hot cider, eating ice cream, and sitting on the rocks while looking at the marina and Motif #1, one of the most painted buildings in the country.
For dinner that evening, we tried Ellen’s Harborside which did not disappoint. He had the lobster roll and I tried the black bean veggie burger.
The next morning, we awoke early to see the sunrise from Halibut Point State Park on Gott Ave. We parked in the lot and scurried down the path, past the quarry, and out to the rocks.
Tip: Arrive at least 45 minutes before the actual time of sunrise in order to get the best pictures.
We checked out of Pleasant Street Inn after having breakfast there and then popped over to the Headlands (near Atlantic Avenue) for a different view of the harbor. After one more coffee with a view, we jumped in the car for our drive home.
