Exploring New England Autumn Beauty: Best October Destinations in North Shore, Massachusetts
- Wanderlust Mike
- 11 hours ago
- 5 min read
We've visited New England once before in the Fall, when we traveled to Acadia National Park in Maine. That wonderful experience has lived in our memories ever since! So we decided to return to this rugged, scenic region of our country once again to witness the vivid colors of Autumn!
We were inspired to visit the town of Rockport because scenes from the movie The Proposal drew us there, and Salem because of the movie Hocus Pocus and its colorful Halloween festivities. Here's how you can enjoy them as well!
ROCKPORT
Flying in to Boston Logan International Airport (BOS), we drove to the Sally Webster Inn in Rockport. Other lodging we can recommend in Rockport includes Captain's Bounty On The Beach, which has a nice ocean front view with a beach and rolling waves, and The Cove At Rockport Hotel, which also has nice ocean views.
Our first day in Rockport, Massachusetts, was sunny and wonderful! From blueberry soda to grilled pumpkin muffins, apple cider donuts to fresh haddock sandwiches, we enjoyed our food samplings and shops!
We also enjoyed exploring Rockport Harbor, where the red barn building known as Motif #1 sits iconically at the end of Bradley Wharf.
Millbrook Meadow and Pond in Rockport is just across the street from the beach. It's a very nice park and great place to relax and take a stroll.
For dining we recommend The Fish Shack, with good food and awesome views! And Rockport House of Pizza and Roast Beef is Greek owned with good handmade pizza!
While in Rockport we had the opportunity to work with Holly Doyle Photography @hollydoylephotography to capture a few photos of us and our nephew and his girlfriend. We've never done this before, and absolutely loved having some scenic outdoor photos to help commemorate our trip. Thanks Holly!
We love experiencing a variety of activities when we travel, so when I discovered that we could sail on a schooner @schoonerlannon_ in Gloucester, Massachusetts, I jumped at the opportunity! We couldn't have asked for better weather. Sunny, with smooth waters and a calm ocean breeze.
Halloween on the Hill, at Long Hill in Beverly, Massachusetts @thetrustees, was a local event we discovered while exploring the North Shore! Full of jack-o-lanterns and animatronics, this child-friendly activity was a feast for the eyes!
Cider Hill Farm @ciderhill_farm in Amesbury, Massachusetts, is a great place to try some fresh cider donuts and hot apple cider! Their store has an incredible variety of products and foods as well.
The medieval Hammond Castle Museum @hammondcastlemuseum in Gloucester, Massachusetts, was constructed by John Hays Hammond Jr. It first broke ground in 1926, and finally became a private non-profit property in the 1970s.
It was constructed to replicate a 13th century French Gothic cathedral. Today, it is open for public tours and special events. Even on a rainy day like we had, we highly recommend a visit!
Russell Orchards @russellorchards, in Ipswich, Massachusetts, has a long history as a working farm. The first trees were planted in 1920 by Dr. Joseph Goodale as a pastime for his son. The fruit sold primarily at market in Boston.
Castle Hill on the Crane Estate, a Stuart-style mansion, was inspired by 17th century English country houses. Today known as the Great House, it was completed in 1928 by Chicago architect David Adler. And the tour guides dress up as maids! @craneestate_trustees
Appleton Farms @appletonfarms in Ipswich, Massachusetts, has many miles of rolling trails through native forest. It's a wonderful place to get out and enjoy nature!
The Shipyard Tavern in Essex opened in 2025 and has a nice variety of food, good service, and great views of Pike Marine marina, Essex River, and Great Marsh!
In 2010, Rockport Music, in the quaint Cape Ann town of Rockport, Massachusetts, celebrated the opening of the Shalin Liu Performance Center! @shalinliuperformancecenter
A state-of-the-art concert hall designed by Alan Joslin and Deborah Epstein, it offers beautiful ocean views and world-class acoustics. We definitely recommend catching a performance when you're in town!
The Cape Ann Community Cinema is a quirky little movie theater full of independent films. The rooms are full of living room furniture!
For washing your laundry, Twin Lights Laundry is nearby, with $4.50 to wash and 25 cents per 5 minutes to dry.
Recommended farms, fairs, and festivals:
Cider Hill Farm - pumpkins, apples, cider donuts, livestock, store, pick your own produce, live music and events
45 Fern Ave, Amesbury, MA 01913
Store open 8 am to 6 pm
We were there during their Fall Weekends celebration, with free live music, a photo wagon, lots of fresh cider donuts & apple cider, hayrides!
Russell Orchards Farm & Winery - pumpkins, apples, livestock, cider donuts, store, bakery with seasonal pies, pick your own produce, fruit wines
143 Argilla Rd., Ipswich, MA 01938
Store open 9 am to 6 pm, closed Mondays
Appleton Farms - barnyard and garden, farm store, programs and events, hiking (12 miles of paths)
MA-1A, South Hamilton, MA 01982
Store open 10 am to 4 pm, closed Mondays
Property is open daily, Sunrise to Sunset.
Non-member parking fee: $6 weekdays/$10 weekends and holidays.
207 Boston Street, Topsfield, MA 01983
Founded in 1818, this is one of the oldest fairs in the country! Taking place in the first half of October, they feature live music, carnival rides, Northeast harvest produce, a show arena, food and concessions, a pumpkin weigh-in, and more!
Harvest Fest in Rockport, MA, is another great local community event!
Tip: For the farms, try to come on a week day, not the weekend. They can get crazy on the weekends during the Fall!
SALEM
Long time fans of the movie Hocus Pocus, and curious about the Halloween festivities along the East Coast, we took the plunge into "The Witch City" of our country. Salem Massachusetts @destsalem is known as Witch City USA due to its history with the witch trails of the 1600s.
In 1692 and 1693, nineteen people were found guilty of witchcraft and executed by hanging. Prior to that, the native Naumkeag people had lived there for thousands of years. The first European settlers arrived in the early 1600s.
Today, Salem has become a destination for Halloween celebrations! Since 1982, they've held an annual Salem Haunted Happenings @hauntdhappnings festival, with haunted houses, psychic readings, outdoor markets, and many people in costume!
Essex Street pedestrian walkway is definitely where all of the action is! This is where you'll find many of the shops, attractions, and folks in costume.
The Haunted Happenings Marketplace takes place at Salem Common from 10 am to 8 pm on Saturdays and 10 am to 6 pm on Sundays during the month of October. There are also many food truck vendors along the West side of the park.
Pioneer Village in Salem, Massachusetts, was built in 1930 and is America's first living history museum! The village sits on three acres of land and contains various examples of 17th-century colonial life.
It was made famous as the home of Thackery Binx in the 1993 Disney movie Hocus Pocus!
Here are some additional Hocus Pocus sites:
Max's house
Allison's house
We thoroughly enjoyed our time in North Shore, Massachusetts! Rockport, Ipswich, Amesbury, Gloucester, Beverly, and Salem were all wonderful places to visit. We encourage you to come and visit this dash of natural beauty, rustic charm, and colonial history for yourself!