While many people flock to Cape Ann in the summer for its stunning beaches, famous whale watches and countless water activities, this gem of a region on Boston’s North Shore takes on a much quieter, more serene vibe during the winter months.
Winter on Cape Ann offers the perfect combination of charm and tranquility – without all the crowds. And while the weather may be a little frosty, it offers a different perspective to appreciate about this historic region.
While some seasonal spots may be closed during the colder months, there are still plenty of activities to keep you busy. As a North Shore native, Cape Ann is one of my go-to destinations for dining, exploring trails and enjoying year-round adventures.
Here’s some of my favorite things to do on Cape Ann during the winter months.
1. Dine in an Igloo
Igloo dining has become an increasingly popular trend, offering a cozy and unique way to enjoy outdoor dining during the colder months. The Mile Marker One restaurant in Gloucester has fully embraced the trend with their new waterfront igloos, which replaced their homemade version previously used for the last several years.
These new heated domes feature twinkling lights and stunning marina views, creating a magical winter dining experience. You can enjoy private dining with up to 8 people in the Igloos or book the “Ice Cave” for larger groups up to 22 people. The BigLoo Lounge is the largest Igloo which is open during restaurant hours with limited first come first serve seating. While there is a fee to dine in the igloos, no fee is required to dine in the Lounge and walk ins are encouraged.
What better way to enjoy some fresh seafood and creative cocktails while taking in the incredible water views while toasty inside an igloo.
2. Check Out Some Ice Sculptures
Gloucester’s So Salty weekend event invites visitors to experience the city’s rich maritime history and artistic spirit in the quiet season.
Typically held the end of January, the So Salty event has gained momentum over the last few years and features ice sculptures crafted by talented local artists, lots of family-friendly activities, art gallery open houses, and specials from the local cafes and shops.
This quiet time is the perfect opportunity to experience Gloucester’s thriving arts community, shop at unique local boutiques, and enjoy the coastal views that define this historic seaport.
3. Indulge in Some Retail Therapy
Cape Ann is home to some fabulous shops and boutiques and many are open year-round.
In Rockport, you’ll find the streets of Bearskin Neck a lot quieter than the summer but that makes it an ideal time to explore this charming area without the bustling crowds. While many of the seasonal shops close for the season, some stay open year-round, offering some unique finds.
Some of my favorite stores that brave the colder weather are the Pewter Store, Shore Thing, Floating Locus and the Rockport Candle Company. A few of the art galleries also keep their doors open year round so you can browse.
At the end of Bearskin Neck, you’ll find the ocean and a large rock barrier, where you’ll be rewarded with stunning views of the breakwater.
While in Rockport, a stop by the iconic Motif No. 1 is always in season! Don’t forget to snap some photos, especially if there’s a dusting of snow – it’s postcard-perfect.
Gloucester’s Main Street offers more great shopping with a mix of unique boutiques and locally owned shops.
Stroll along the snow-dusted sidewalks and discover treasures like handcrafted jewelry, nautical-themed home decor, and one-of-a-kind art pieces. Some of my favorites are Local Color to see work from local artisans, The Cave, a purveyor of cheese, wine and chocolate, and the Brass Monkey an emporium of gifts, apparel, ornaments and so much more.
Warm up with a coffee or hot chocolate from one of the inviting cafes as you explore, and enjoy the slower pace of winter shopping without the summer crowds.
4. Listen to Live Music
Gloucester is one of my favorite places to go to listen to live music any time of the year.
With venues like The Cut Bridge and Minglewood Harborside you’ll find a mix of local talent and lively atmospheres with great music.
5. Take an Invigorating Walk on the Beach
There’s something special about the beach at wintertime, especially when it is covered in a blanket of fresh snow.
Winter transforms Cape Ann’s beaches into a peaceful retreat. The crisp air and crashing waves are the perfect way to invigorate and clear your mind. You may even get a chance to see some winter surfers riding the icy waves! Just be sure to bundle up as it can be a bit frigid.
6. Discover Cape Ann’s Bookstores
I can’t resist a good bookstore, and there’s nothing better than curling up with a coffee and a great book on a chilly day.
Gloucester’s Main Street is home to two fantastic bookstores. The Bookstore of Gloucester carries a wide selection of books, including a curated selection of new releases and a section of books by local authors.
Across the street is Dogtown Books with its treasure trove of rare and used books. You never know what you may find in there. On a recent visit, I was thrilled to discover an old 1958-1959 book “Harbors of New England” written by Gulf Oil, complete with old photos and detailed descriptions of harbors from New London, CT to Jonesport, ME. What a perfect find to add to my growing New England book collection!
In the heart of Manchester-by-the-Sea, you’ll find Manchester By The Book. This cozy, independent bookstore offers a carefully selected range of books, from bestsellers to local authors, along with stationery, gifts, and more.
Stopping by one of Cape Ann’s book stores is the perfect way to spend a quiet winter afternoon.
7. Pamper Yourself at a Spa
Winter is the perfect season for a little self-care, and Cape Ann is home to several boutique spas where you can relax and unwind. Indulge in a day of tranquility at Saltwater Massage Studio in Gloucester, where their therapeutic massages and wellness treatments will melt away the winter blues and leave you feeling refreshed and renewed.
8. Attend an Event at Hammond Castle Museum
Perched overlooking the Atlantic in Gloucester, the Hammond Castle Museum showcases unique architecture and intriguing exhibits. While this historic museum is not open for tours during the winter, it does offer some unique winter events where you can experience the castle.
Winter Tip: Visit the Hammond Castle website to see the latest events and be sure to Buy tickets in advance to reserve your spot.
9. Go Antique Shopping in Essex
Essex is renowned for its antique shops and many are open year-round so you can easily spend a day hunting for treasures. The quieter winter months mean less competition for hidden gems, and shop owners often have more time to share the fascinating stories behind their pieces.
With over a dozen antique shops lining the scenic Essex Coastal Scenic Byway, you can spend a chilly afternoon browsing through collections of maritime relics, vintage furniture, rare books, and unique collectibles. The great thing about antique shopping is you never know what unique finds you’ll uncover.
After your shopping adventure, head to Woodman’s of Essex, open year-round, to indulge in their legendary fried clams or enjoy a fireside meal at one of Essex’s charming seafood restaurants, making for a perfect winter day steeped in history and charm.
10. Explore Halibut Point State Park
Halibut Point State Park in Rockport is a historic granite quarry with breathtaking winter views of the Atlantic Ocean. There are several trails around the quarry that are manageable even in light snow, making it a great place for an outdoor escape.
During the winter, you can explore Halibut Point State Park on your own or join one of the guided programs that highlight its World War II history, granite quarrying past, and seasonal wildlife.
With panoramic ocean views and fewer crowds, winter is such a peaceful time to experience the park’s rich history and natural beauty.
11. Enjoy a Scenic Drive
One thing I love about Gloucester is everywhere you turn there seems to be stunning views of the ocean! My favorite drive takes you along the Essex Coastal Scenic Byway which winds through some of the most picturesque towns on the North Shore of Massachusetts.
The Byway stretches 90 miles along the North Shore, connecting 14 coastal communities from Lynn to Salisbury, with the most breathtaking sections found on Cape Ann. Along the way, you’ll get to see the rugged coast line, historic landmarks, scenic farmland and the vast expand of the Great Marsh.
12. Learn about Gloucester’s Maritime History
Learn about Cape Ann’s rich maritime history at Maritime Gloucester. Even in winter, this museum offers engaging exhibits and a well-stocked gift shop featuring nautical-themed items and local crafts.
13. Explore the Outdoors
Winter on Cape Ann is the perfect time to bundle up and hit the trails for some fresh air and stunning scenery. Some of my favorite places to explore are Halibut Point State Park in Rockport, Willowdale in Ipswich and Appleton Farms’ wide carriage roads. All offer peaceful, wooded trails that are great for a snowy hike or even some light snowshoeing.
While there are lots of nature trails in Cape Ann, if you are not familiar with the area, you may want to go on a guided hike or walk.
CraneOutdoors, part of the Trustees of Reservations, offers some awesome winter adventures, like guided hikes and snowshoeing. You can even trek through the Castle Neck dunes on a full moon hike to spot Snowy Owls and other winter birds while learning about the local wildlife.
If you’re not up for the woodlands, a stroll along Gloucester’s causeway is always a treat.
14. Attend a Culinary Workshop at Appleton Farms
Appleton Farms in Ipswich is a working farm which offers all sorts of hands-on culinary workshops throughout the winter. This is a great time to learn how to make seasonal dishes using farm-fresh ingredients while enjoying the rustic charm of this historic property.
During Maple Sugaring season, the Sugar Shack also opens up where you can get a taste of some local maple syrup.
The farm is also hot spot for cross country skiing as well. Bring your skis and hit the snow covered trails. Don’t forget to stop by the store for some homemade treats.
15. Dine at Some Incredible Restaurants
Cape Ann is famous for its seafood, and winter is no exception. Warm up with a hearty bowl of clam chowder at The Causeway Restaurant or enjoy some fresh catches at local favorites like The Seaport Grille or Woodman’s of Essex.
16. Check out the Cultural Scene
Cape Ann’s arts scene stays alive in the winter with several performance venues.
The Shalin Liu Performance Center in Rockport provides a year-round schedule of concerts and films paired with stunning ocean views. The Gloucester Stage hosts intimate productions that captivate audiences.
The Bottom line
Winter on Cape Ann is the perfect time to slow down and enjoy the season. Whether you’re browsing antique shops, having dinner in a cozy igloo, or taking in the stunning views at Halibut Point, there’s plenty to love. So bundle up, grab a hot drink, and see for yourself why Cape Ann is just as special in winter as it is in summer.
With fewer crowds and a peaceful coastal vibe, Cape Ann in winter feels like a hidden gem. It’s the perfect chance to soak in the scenery, explore local spots at a relaxed pace, and experience a different side of this New England treasure. Throw on your coat, lace up your boots, and embrace the magic of Cape Ann in the off-season—you just might end up loving it the most.
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