While many visitors flock to Cape Ann in the summer for its beaches, whale watching and water activities, this scenic region on Boston’s North Shore takes on a quieter, more serene vibe during the winter months.
What to Expect in Winter on Cape Ann
Winter on Cape Ann is quieter and more peaceful than the busy summer months. It has a slower pace with fewer crowds, allowing you to experience the area’s historic seaside towns in a more relaxed and authentic way.
Even though some seasonal spots close for the winter, there’s still plenty to do, making it an ideal destination for a low-key winter getaway. Think quiet walks on the beach, cozy dining and peaceful trails.
Expect chilly temperatures, occasional snow, and windy ocean breezes, so dress in layers and bring warm footwear for outdoor adventures.
As a North Shore native, Cape Ann is one of my favorite places to visit year-round for dining, exploring and outdoor adventures.
Here’s some of my favorite things to do on Cape Ann during the winter months.
- Outdoor Adventures
- Cultural and Indoor Activities
- Indulge in Some Retail Therapy
- Unique Winter Activities on Cape Ann
- Dine at Some Incredible Restaurants
- Where to Stay
- The Bottom Line
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Outdoor Adventures
One of the best parts of visiting Cape Ann in the winter is how peaceful the outdoors becomes. From coastal walks, hiking trails and birding, there are countless opportunities to explore outside. Just be sure to bundle up as it can get a bit chilly!
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 at Good Harbor Beach!
Check out my Ultimate Guide to Beaches North of Boston for information on the best Cape Ann beaches to visit any time of year.
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.
Hit One of the Nature Trails
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 Willowdale State Forest and Appleton Farms in Ipswich. Each offer peaceful, wooded trails that are great for a snowy hike, light snowshoeing or even cross country skiing.
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 at Crane Beach on a full moon hike to spot Snowy Owls and other winter birds while learning about the local wildlife.
Visit the Fisherman’s Memorial
If you’re not up for the woodlands or beach, a stroll along Stacy Boulevard to see the Fisherman’s Memorial is especially moving in the winter months. With fewer visitors and sweeping views of Gloucester Harbor, it’s a quiet, reflective spot that highlights Cape Ann’s deep maritime history.
Cultural and Indoor Activities
Winter is the perfect time to step inside and explore Gloucester’s vibrant arts and cultural scene and other indoor activities if it’s a bit too cold outside.
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 and Minglewood Harborside you’ll find a mix of local talent and lively atmospheres with great music.
Learn about Gloucester’s Rich Maritime History
Visit Maritime Gloucester to learn about Gloucester’s role as America’s oldest fishing port. This hands-on museum offers engaging exhibits and is a perfect indoor activity on a chilly Cape Ann day. Be sure to browse their well-stocked gift shop featuring nautical-themed items and local crafts.
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 Revive Wellness in Gloucester, where their therapeutic massages and wellness treatments will melt away the winter blues and leave you feeling refreshed.
If it’s too cold for the beach, you can still soak in the benefits of salty air during a Himalayan Salt Cave halo-therapy session.
See a Performance
Cape Ann’s cultural scene definitely stays alive in the winter with several great performance venues. The Shalin Liu Performance Center in Rockport provides a year-round schedule of concerts and films, all with stunning ocean views as a backdrop. The Gloucester Stage hosts intimate theatrical productions for a cozy winter evening. Check their website for the latest events.
Attend a Culinary Workshop or Event at Appleton Farms
Appleton Farms in Ipswich is a working farm which offers all sorts of hands-on culinary workshops and events 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 a 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.
Indulge in Some Retail Therapy
Cape Ann is home to some fabulous shops and boutiques and many are open year-round.
Stroll Along Rockport’s Bearskin Neck
Some of my favorite Rockport 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 for a perfect postcard photo.
Explore Gloucester’s Main Street
Gloucester’s Main Street offers more great shopping with a mix of unique boutiques and locally owned shops.
Stroll along the snow-dusted sidewalks while browsing shops filled with handcrafted jewelry, nautical home decor, and unique works of art. 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 enjoy the slower pace of winter shopping without the summer crowds.
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 which carries a wide selection of books, including 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.
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 a relaxing way to spend a quiet winter afternoon.
Unique Winter Activities on Cape Ann
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. These 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.
Enjoy a Scenic Drive
One of the things 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.
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.
Take in the rocky coastline and winter landscapes from the warmth of your car! Along the way, you’ll have plenty of photo-ops of the rugged coast line, historic landmarks, scenic farmland and views of the Great Marsh.
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 at the end of January, the So Salty event has grown in popularity over the past few years. It features ice sculptures created by talented local artists, along with plenty of family-friendly activities. Visitors can also enjoy art gallery open houses and special offerings from local cafes and shops.
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.
Dine at Some Incredible Restaurants
Cape Ann offers a mix of dining experiences to suit every mood and occasion. From cozy pubs to iconic seafood spots and upscale dining, there’s something for every taste.
Here are a few favorites:
The Causeway Restaurant (Gloucester) is a longtime local favorite known for its classic New England seafood and award-winning clam chowder.
The Seaport Grille (Gloucester) offers elevated seafood and steaks with harbor views, making it a great choice for a relaxed but slightly upscale winter dinner.
The Farm Bar & Grille (Essex) is a rustic pub-style restaurant which is known for its comfort food and relaxed vibe. Their pulled-pork mac & cheese and steak and cheese egg rolls are a family favorite.
Woodman’s of Essex (Essex) which is known for creating the fried clam is an iconic spot for seafood in a casual setting.
Tonno Restaurant (Gloucester) is popular for its Italian-inspired seafood dishes, creative cocktails, and cozy atmosphere during the winter months.
Where to Stay
With cozy inns, beachfront hotels, and charming B&Bs across Cape Ann, it’s easy for a day trip to turn into a relaxing winter weekend escape. Here are some great recommendations for a perfect winter getaway.
Beauport Hotel – This upscale waterfront hotel in Gloucester is right on the water and has sweeping ocean views, an onsite restaurant and a cozy fire-pit deck perfect for a winter stay.
Rockport Inn & Suites – This family friendly Inn situated on 5 woodland acres is just a short walk to downtown galleries, shops, and beaches. The Inn offers complimentary continental breakfast, a heated indoor pool and a patio with fire‑pits for a cozy evening.
The Bottom Line
With fewer crowds and a peaceful coastal vibe, Cape Ann in winter feels like a hidden gem. It’s the perfect chance to slow down and enjoy the season. Whether you’re browsing shops, having dinner in a cozy igloo, or taking in the stunning ocean views, there’s plenty to love about Cape Ann during the off-season. 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.
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