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Day Tripping: 12 Hours in Rockport

Shopping, gallery hopping, and strudel in a picturesque North Shore town

A sunset view of Rockport Harbor from Bearskin Neck. Photo by Abby Jordan

You may not think of an ocean-side town as a fall destination. But with its cool sea breezes, colorful leaves, and many art galleries, the North Shore’s Rockport is the perfect place to spend an autumn day.

9 a.m. — All Aboard
Rockport is just 40 miles north of Boston and is the easternmost town on Cape Ann, a section of land that juts into the Atlantic Ocean. To get to Rockport, take the Newburyport/Rockport commuter rail line from North Station. Tickets are $7.75 per ride, and the trip is just over an hour.

10:15 a.m. — Arrival and Quick Walk to Town
Once you arrive, head down Railroad Avenue and pick up Broadway or Main Street for the short walk into the main part of town. Bearskin Neck, the small peninsula in Rockport Harbor, used to be a busy fishing dock and is now home to restaurants, shops, art galleries, and beautiful views. Look for Motif No. 1, the red fishing shack adorned with buoys, which has been built and rebuilt several times since 1884. It is said to be one of the most photographed and painted buildings in the country — so don’t forget your camera.

10:30 a.m. — A Snack and Shopping
If you need a midmorning pick-me-up, head to Helmut’s Strudel (69 Bearskin Neck, 978-546-2824) for an espresso and strudel. Then spend some time poking around the shops and galleries on Bearskin Neck, such as the John Caggiano Gallery (66 Bearskin Neck, 978-546-2414) or the Good Dog! Gallery (36 Bearskin Neck, 978-546-1364) for all kinds of dog-themed paintings, prints, and gifts.

Artists have long been drawn to Rockport’s beauty. With more than 25 galleries, the town is also an art-lover’s heaven. Shop for paintings, ceramics, photography, and more. For a complete list of artist galleries, click here.

Noon — Lunchtime
Once you’ve worked up an appetite for lunch, you’ll find plenty of restaurants and sandwich shops to choose from. The Greenery Restaurant (15 Dock Square, 978-546-9593), with its scenic views of Rockport Harbor, offers an array of sandwiches, seafood, salads, and a selection of tasty desserts. If you’re looking for more casual fare, head to Top Dog of Rockport (2 Doyles Cove Rd., 978-546-0006), which serves any kind of hot dog you can think of — as well as chicken fingers and fried clams.

If you’ve got a hankering for seafood, check out the self-serve Lobster Pool Restaurant (329 Granite St., 978-546-7808), which also has water views and a fish-house atmosphere. A more upscale restaurant is My Place by the Sea, at the tip of Bearskin Neck (978-546-9667).

1 p.m. — Jump Ship
Rockport is home to many beautiful beaches. Back Beach is near downtown, between Main and Granite streets. Front Beach is also close by, just off Main Street in Sandy Bay. The cool fall temperatures also make the beaches a perfect place to picnic if you grab a sandwich or salad to go from town.

Or you can venture out to sea on the Schooner Appledore III (Tuna Wharf, Bearskin Neck, 978-546-7540), which offers one-and-a-half-hour trips, or with Sailor Dog Charters (978-460-0780), which has hour-long or daylong trips.

4 p.m. — Land-ho!
Once you’ve gotten your fill of being at sea, there are a few more things to check out on dry land. One of them is a house made entirely from newspaper, in 1922 (52 Pigeon Hill St., open spring through fall). Admission is $1.50.

After you’re done marveling at the paper house, head to Halibut Point State Park and take a quarry tour or explore the tidepools.

6 p.m. — Dinner Bell
Rockport offers many choices for dinner, including the Blacksmith Shop Restaurant (23 Mt. Pleasant St., 978-546-1600), which has been open since 1927. The seafood and entrees start at $16.95. For more casual dining, try the sandwiches, salads, and “New England favorites” at Brackett’s Ocean View Restaurant (25 Main St., 978-546-2797).

8 p.m. — Homeward Bound
Catch the train back to Boston. But first, you’ll want to stop by the Rockport Fudgery (Tuna Wharf, Bearskin Neck, 888-383-4379) or Tuck’s Candies (915 Main St., 978-546-6352, 800-569-2767) to grab a sweet treat for the ride home.

Click here to explore more day trips from Boston.

Abby Jordan can be reached at ajordan@bu.edu.