12 Best Things to Do in Boston in Winter: Unmissable Attractions & Activities

by Jen
Best Things to Do in Boston in Winter
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Embrace the winter charm of Boston! From gliding across the ice at the Frog Pond to wandering through the festive Beacon Hill Holiday Stroll, get ready for a mix of excitement and enchantment in this historic city. Here are all the coolest things to do in Boston this winter.

Winter here in Boston is something special. As a local, I’ve always loved how our city transforms into a frosty playground. We’ve got everything from holiday markets and festivals to iceskating on Frog Pond. I’m excited to share my favorite winter activities in Boston, perfect for both long-time residents and first-time visitors.

Whether it’s catching the dazzling holiday lights in the Common or enjoying a warm evening at the Boston Wine & Food Festival, there’s a unique charm to Boston in winter. So, grab your scarf and let’s uncover all of the exciting things to do in Boston this winter. It’s a season full of surprises and delights right here in our backyard!

The top places to visit in Boston in winter

Top 12 Winter Attractions in Boston, MA

Eager to discover the best activities in Boston this winter? Trust me, Boston is overflowing with experiences perfect for all kinds of adventurers- from teens to seniors. Keep reading to uncover the top spots and things to do in Boston during the frosty months.

Excited to skate on the Frog Pond in Boston Common? Or perhaps you’re looking forward to the enchanting holiday lights in the Common and Public Garden? Whether you’re planning to stroll through the historic Beacon Hill during its Holiday Stroll or explore the SoWa Winter Festival, Boston offers a plethora of fantastic winter activities for everyone. Let’s dive in!

1. Explore the Holiday Market at Snowport

One of my all-time favorite winter activities in Boston is the Holiday Market at Snowport. This vibrant market, running from November 10 through December 31, is a winter wonderland in itself. As a local, I can tell you it’s a market that celebrates our community’s spirit.

Picture this: over 120 local artisans and businesses showcasing their unique crafts and goods. From handcrafted blades by Faraway Forge to whimsical art pieces by Ashley Eisenman Art, there’s a treasure for everyone. And let’s not forget the food! The market offers an array of mouth-watering options. Whether it’s the Swiss-style Raclette from Baked Cheese Haus or the traditional French crepes from The Frenchman’s Crepes, your taste buds are in for a treat.

But what truly sets this market apart are the festive bars. The “Jingle Bar” with its hundreds of bells and “The Drizzy Dreidel” with spinning dreidels create a holiday atmosphere like no other. And for those looking for a warm winter treat, the Holiday Hot Mulled Cider by Downeast Cider is a must-try.

The market also features a 10-foot-tall Mistletoe Archway and a Winter Wish Wall, perfect for those Instagram moments. And for the crafty ones, the Crafting Corner by The Maker’s Club offers workshops to make holiday-themed crafts.

Open seven days a week, with extended hours during the peak holiday season, the Holiday Market at Snowport is a must-see for anyone looking for fun places to visit in Boston in winter. It’s a place where you can shop, eat, drink, and soak in the festive spirit, all in the heart of Boston Seaport.

The Holiday Market at Snowport is one of the best things to do in Boston in winter.
The Holiday Market at Snowport is a cherished winter wonderland celebrating community spirit.

2. Attend the Boston Wine & Food Festival

If you’re a foodie or wine enthusiast, the Boston Wine & Food Festival is an unmissable winter event. Running from January 12th through March 29th, 2024, this festival is a culinary journey you’ll want to savor.

Hosted at the luxurious Boston Harbor Hotel, the festival offers an array of events that are sure to delight your senses. Imagine themed weekends, winemaker-hosted dinners, and tastings that showcase the best in wine and food pairings. The festival’s 35th edition promises an even more captivating experience.

Each event is a unique opportunity to indulge in world-class wines and gourmet cuisine. From the Opening Night with its sophisticated wine tasting to the thematic dinners, every evening is a celebration of flavor and craftsmanship. The festival also includes interactive seminars and brunches, perfect for both wine connoisseurs and those looking to expand their palate.

I recommend attending one of the intimate winemaker dinners. It’s an experience where the stories behind the wines are as enriching as the flavors. And for a truly special evening, the reserve dinners offer an exclusive taste of some of the world’s finest wines.

The Boston Wine & Food Festival is more than just an event. It’s a journey through the world of wine and food, set against the scenic backdrop of Boston Harbor. It’s one of the best things to do in Boston in winter for anyone who appreciates the finer things in life.

The Boston Wine & Food Festival isn't just an event; it's a journey through the world of wine and food.
The Boston Wine & Food Festival isn’t just an event; it’s a journey through the world of wine and food. | Image Source: https://boswineexpo.com/

3. Ice skate on Frog Pond

Ice skating on Frog Pond in Boston Common is a quintessential winter experience. Trust me, there’s something magical about gliding over the ice with the city’s historic backdrop. It’s a must-do for both locals and visitors.

The Frog Pond becomes a bustling hub of activity during the winter months. The crisp air, the laughter of skaters, and the twinkling city lights create an enchanting atmosphere. Whether you’re a seasoned skater or lacing up for the first time, the Frog Pond welcomes everyone.

What I love most is the sense of community it brings. Families, couples, and friends all come together here, sharing moments of joy and warmth. And if you’re feeling a bit wobbly on the ice, no worries! There are skating aids for beginners and skate rentals available, making it accessible for all.

After some fun on the ice, you can warm up with a hot cocoa from the nearby café. It’s the perfect way to end your ice skating adventure in Boston. Hands down, skating on the Frog Pond is one of the most fun things to do in Boston this winter. It’s a way to create lasting winter memories in the heart of the city.

Ice skating offers a magical glide against the city's historic backdrop—a must for all.
Ice skating offers a magical glide against the city’s historic backdrop—a must for all.

4. Enjoy the Boston Celtic Music Festival

The Boston Celtic Music Festival, affectionately known as BCMFest, is a highlight of the winter season in Boston. Scheduled for January 11-14, 2024, this festival is a vibrant celebration of Celtic music, dance, and culture. Without a doubt, it’s one of the best winter attractions in Boston.

Held at venues like Club Passim, Crystal Ballroom, The Burren, and The Rockwell, BCMFest brings together a fantastic mix of local and international talent. The festival showcases a rich tapestry of Celtic traditions, from Irish and Scottish to Cape Breton and Quebecois influences.

What makes BCMFest stand out is its diverse lineup. You’ll find traditional acts alongside contemporary artists, blending classic sounds with modern twists. It’s a place where professional touring acts meet local session musicians, creating a unique and lively atmosphere.

Highlights include participatory events like the Boston Urban Ceilidh, where you can join in social dances with live music. No experience is needed, and it’s a ton of fun! Plus, there are workshops at the Passim School of Music for those who want to dive deeper into Celtic music.

The festival culminates with a performance by the award-winning band Le Vent du Nord, known for their soulful and rhythmic music rooted in the Celtic diaspora. This is a must-attend event for anyone who loves Celtic music or wants to experience something uniquely Bostonian in winter.

The Boston Celtic Music Festival (BCMFest) is a vibrant celebration of Celtic music, dance, and culture.
The Boston Celtic Music Festival (BCMFest) is a vibrant celebration of Celtic music, dance, and culture. | Image Source: https://www.thebostoncalendar.com/

5. Experience First Night Boston

First Night Boston is a spectacular way to ring in the New Year and one of the best free things to do in Boston in winter. Held on December 31 at City Hall Plaza, it’s a celebration that brings the city together in a dazzling display of art, music, and community.

The event kicks off at noon and goes on past midnight, transforming City Hall Plaza into a hub of festivities. What’s great about First Night is its accessibility. It’s free and open to all, making it a perfect family-friendly event.

The highlight for many is the stunning ice sculptures. These intricate works of art, set up around City Hall and Boston Common, are illuminated at night, creating a magical winter landscape. And as the clock strikes midnight, the sky above Boston Harbor lights up with fireworks, welcoming the New Year in grand style.

First Night also offers a range of musical performances and activities throughout the day and night. It’s a celebration that truly captures the spirit of Boston, bringing people from all walks of life together to celebrate the start of a new year.

Remember, public transportation is the best way to get there, as parking can be tricky. So, bundle up, join the festivities, and start your year with a memorable Boston experience!

First Night Boston on December 31unites the city through art, music, and community festivities.
First Night Boston on December 31unites the city through art, music, and community festivities. | Image Source: https://www.firstnightboston.org/

6. See the Holiday Lights in the Common & Public Garden

A winter visit to Boston isn’t complete without seeing the holiday lights in the Common and Public Garden. Visiting this dazzling display is one of the coolest things to do in Boston in winter.

The iconic light display along the Commonwealth Avenue Mall, stretching from Arlington Street to Kenmore Square, is a sight to behold. Inspired by the illuminated tree-lined boulevards of Paris, it’s a tradition that lights up the city from early December to April each year.

Walking through the Common and Public Garden under the glow of these lights is a truly magical experience. The twinkling lights against the backdrop of Boston’s historic parkland create a winter wonderland in the heart of the city. It’s a perfect spot for a romantic stroll or a peaceful evening walk.

The effort to light up these areas is a community-driven initiative, showcasing the city’s commitment to bringing joy and beauty to its public spaces during the winter season. So, wrap up warm and take a walk through this illuminated marvel – it’s a simple yet unforgettable way to experience Boston’s winter charm.

Witnessing the holiday lights in the Common and Public Garden is an essential and enchanting experience.
Witnessing the holiday lights in the Common and Public Garden is an essential and enchanting winter experience in Boston.

7. Take a Winter Wildlife Cruise in Boston Harbor

For a unique adventure, consider a Winter Wildlife Cruise in Boston Harbor. It’s a fantastic answer for anyone wondering what to do in Boston this winter, especially if you love nature and the outdoors.

This cruise offers a rare opportunity to observe the animals that make Boston Harbor their home during the colder months. You’ll be joined by park rangers and local naturalists, providing insights into the wildlife and the surrounding environment.

Imagine cruising through the crisp winter air, with the city skyline receding behind you. The harbor, known for its natural beauty, becomes a serene winter habitat for various wildlife. Keep your eyes peeled for seals basking on the rocks or seabirds gliding over the water.

The Winter Wildlife Cruise is an educational journey. You’ll learn about the harbor’s ecosystem and how these animals adapt to the winter conditions. It’s a perfect blend of adventure and learning. This makes it an ideal outing for families, nature enthusiasts, or anyone looking to try something different this winter.

Remember to dress warmly, as the winter winds can be brisk on the water. One of the most unique things to do in winter in Boston, this cruise offers a peaceful escape from the bustling city life.

Winter Wildlife Cruise in Boston Harbor—a unique adventure ideal for nature and outdoor enthusiasts.
Winter Wildlife Cruise in Boston Harbor—a unique adventure ideal for nature and outdoor enthusiasts.

8. Attend a Bruins Hockey Game

Attending a Bruins hockey game is an electrifying way to spend a winter evening in Boston. As a local, I can tell you there’s nothing quite like the energy in TD Garden when the Bruins hit the ice. It’s a must-do for sports fans and one of the most thrilling winter experiences in Boston.

The atmosphere is electric. Fans decked out in black and gold, the roar of the crowd, and the fast-paced action on the ice make for an unforgettable experience. Even if you’re not a die-hard hockey fan, the excitement is contagious. Trust me, you’ll find yourself cheering along with everyone else!

Grab some classic game snacks like a hot dog or some nachos, and settle in for an evening of top-tier hockey. Watching the Bruins, with their rich history and passionate fanbase, is a quintessential Boston experience.

So, put on your Bruins gear (or at least some black and gold), and get ready for an action-packed night. Whether they win or lose, a Bruins game is always a win for a fun night out in Boston.

Watching a Bruins hockey game at TD Garden is an electrifying winter evening.
Watching a Bruins hockey game at TD Garden is an electrifying winter evening in Boston.

9. Go to the Beacon Hill Holiday Stroll

The Beacon Hill Holiday Stroll is a charming and festive event, perfect for families looking for the best things to do in Boston in winter with kids. Held in early December, this event transforms Charles Street into a winter wonderland.

For over 25 years, the Beacon Hill Business Association has sponsored this event, marking the start of the holiday shopping season. The street, closed to traffic from 5:00 pm, becomes a pedestrian paradise. Imagine strolling through the historic neighborhood with your family, surrounded by holiday lights and the sound of traditional bell ringers.

The festivities begin early at the Hill House Community Center, where kids can meet Santa and take photos. This is always a hit with the little ones! At 7:00 pm, the community gathers for the Beacon Hill tree lighting, a magical moment that truly captures the spirit of the season.

The stroll is a community celebration. Victorian carolers, live music, and local shops offering refreshments add to the festive atmosphere. It’s a wonderful evening of holiday cheer for all ages and a delightful way to experience the charm of Beacon Hill during the holiday season. For me, this is one of the prettiest spots in Boston that I recommend everyone visit.

The Beacon Hill Holiday Stroll in early December transforms Charles Street into a charming winter wonderland.
The Beacon Hill Holiday Stroll in early December transforms Charles Street into a charming winter wonderland. | Image Source: https://www.thebostoncalendar.com/

10. Visit the SoWa Winter Festival

Next up on our list of the best Boston winter attractions is the SoWa Winter Festival. This vibrant and bustling event is perfect for families. It runs from late November til mid December at the SoWa Power Station. It’s a festive extravaganza not to be missed!

This festival is a shopper’s paradise, with over 100 of the region’s top makers, artists, designers, and specialty food vendors. It’s like stepping into a treasure trove of unique gifts and goodies. As someone who loves finding one-of-a-kind items, I can assure you, it’s a delightful experience.

But the SoWa Winter Festival is more than just shopping. There’s delicious food, specialty bars, and hot beverage stations to keep you fueled and warm. The live music adds a lively atmosphere, which makes it a fun outing for the whole family.

For a bit of relaxation, head to the second-level Mezzanine Bar. It’s a great spot to take a break and soak in the holiday spirit. And if you’re in the mood for a meal, nearby Marseille offers nightly delights and a cool bar.

The SoWa Winter Festival is a wonderful way to enjoy the holiday season in Boston. It’s a place where you can shop, eat, drink, and be merry, all under one festive roof.

The SoWa Winter Festival is a vibrant and bustling event perfect for families.
The SoWa Winter Festival is a vibrant and bustling event perfect for families. | Image Source: https://www.sowaboston.com/

11. Walk the Freedom Trail

Walking the Freedom Trail is a fantastic way to explore Boston’s rich history, even in winter. This 2.5-mile trail takes you through 16 historically significant sites, offering a unique perspective on America’s past.

The trail starts at Boston Common and winds its way through the city, passing landmarks like the Massachusetts State House, Faneuil Hall, and Paul Revere’s House. Each site tells a story, making the walk both educational and fascinating.

In winter, the crisp air and fewer crowds make for a peaceful journey through history. I recommend bundling up and stopping for a warm drink along the way. It’s a great opportunity to reflect on the city’s role in the American Revolution.

Don’t forget to visit the Old North Church, where the famous “One if by land, and two if by sea” signal was sent. It’s a moment that always gives me chills, thinking about the bravery of those early revolutionaries.

Walking the Freedom Trail in winter is a serene experience, with the chill in the air making the warm moments in cozy cafes along the way even more delightful. It’s one of the best things to do in Boston in winter, offering a blend of education, exercise, and stunning winter scenery.

Explore the city's rich history by traversing the 2.5-mile Freedom Trail.
Explore Boston’s rich history in winter by traversing the 2.5-mile Freedom Trail.

12. Snowshoeing in the Blue Hills Reservation

For the final stop on our winter tour of Boston, let’s venture just outside the city to the Blue Hills Reservation for some snowshoeing fun! It’s an exhilarating day trip to experience the beauty of a winter in New England.

Imagine strapping on snowshoes and trekking through the snowy landscape. The Blue Hills, with their rolling terrain and scenic vistas, become a winter playground. The crisp air, the crunch of snow underfoot, and the serene beauty of the snow-covered hills make for an unforgettable experience.

Snowshoeing here is great for all skill levels, whether you’re a seasoned pro or trying it for the first time. The reservation offers a variety of trails, so you can choose your own adventure. And the view from the top of Great Blue Hill? Absolutely breathtaking! You can see the Boston skyline in the distance, a stunning contrast to the natural beauty around you.

After a day of snowshoeing, nothing beats sharing stories over a hot cocoa. It’s a perfect way to end a day of winter exploration. Snowshoeing in the Blue Hills Reservation is one of the most fun activities in Boston in winter, hands down.

Conclude your tour with exhilarating snowshoeing at the Blue Hills Reservation.
Conclude your winter Boston tour with exhilarating snowshoeing at the Blue Hills Reservation.

Frequently Asked Questions (FAQs) about the Best Things to Do in Boston in Winter:

Looking for more content on the best Boston things to do in winter? Here are some popular questions (and answers) I get that will help you plan your winter vacation to Boston, Massachusetts.

Is it worth visiting Boston in the winter?

Absolutely! Boston in winter is a wonderland. The city transforms with festive lights and snow-covered parks. There’s ice skating on Frog Pond, cozy cafes, and winter festivals. Plus, it’s less crowded, so you can enjoy the city’s charm more peacefully.

What do you wear in Boston in the snow?

Layer up! Start with thermal underwear, add a fleece or sweater, and top it off with a waterproof winter coat. Don’t forget a hat, gloves, and a scarf. For your feet, waterproof boots with good traction are essential. Layers are key because indoor places are well-heated.

A woman dressed in winter attire walking through Boston streets.
A woman dressed in winter attire walking through Boston streets.

What month is Boston the coldest?

January is usually the coldest month in Boston. Temperatures often dip below freezing. It’s chilly, but with the right clothing, you can still enjoy all the outdoor fun Boston offers in winter.

Is Boston fun at Christmas?

Boston is magical at Christmas! The city lights up with holiday decorations. There’s the Christmas tree at Boston Common, holiday markets like the SoWa Winter Festival, and festive events all over the city. It’s a great time to experience Boston’s holiday spirit.

Is it expensive to visit Boston?

Boston can be pricey, but there are ways to save. Look for hotel deals in winter, as it’s off-peak season. Many attractions, like walking the Freedom Trail, are free. Eating at local diners or food trucks can save money too. Plan and budget, and you can enjoy Boston without breaking the bank.

The top things to do in Boston in winter for all types of travelers
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