Boston, MA is consistently ranked as one of the best cities in America. With its impressive role in America’s history (hello, Paul Revere), to its modern renaissance as a tech and business hub, you can’t go wrong with planning a trip to Boston. But what about in winter? Isn’t it hella cold and nasty? Yeah, sometimes. But there are still a wealth of things to do in Boston in winter, and thankfully, most of them are inside!
I’ve lived in Boston for 10 years (where did the time go?!). I actually hate the cold, but I love the vibrant cultural and dining scene that Boston offers. Therefore I’ve learned to bundle up and bear the cold, and I’ve amassed a lot of knowledge on things to do in Boston in winter.
You have to get out and explore the city, and luckily winter is a great time to do so. Winter is an ideal time to explore, you say? Yes! There are way less crowds and tourists in the winter, giving you a much better chance of seeing our best sights without a wait.
I wanted to go over some of my top recommendations for things to do in Boston in winter like things to do in Boston at night, a few fun date ideas in Boston, our amazing Boston museums and entertainment options, fun restaurants in Boston, and where to shop in downtown Boston. I’ll also touch on a few places to stay in Boston if you’re looking for a nice hotel. Keep in mind this is just a short list of the things I personally like and recommend, but it should still be plenty to keep you busy!
This article contains affiliate links which means I might make a small commission if you purchase something I recommend at no cost to you.
There are so many great hotels in Boston, but I’ll just touch on a few of my favorite recommendations across various price levels:
Mandarin Oriental is the epitome of a luxury hotel. Guests love the professional and friendly staff, the Bar Boulud, and the many facilities like the steam room. It’s attached to the Prudential Center, making it an easy place to start your exploration. ($500+)
My husband and I got engaged at the Taj Boston, so it holds a special place in my heart! Their rooms and suites overlook the Boston Public Garden and their restaurant is to die for. If it’s a special occasion, have some champagne or hot chocolate delivered to your room. ($200+)
The Four Seasons is located just across from the Boston Public Garden with unparalleled customer service, and their concierge team is among the best in the world. Check out the cozy Bristol Lounge for excellent dining and bar options on-site. ($550+)
The Colonnade Hotel is located near Boston Symphony Hall and the Prudential Center, and visitors say they love the access to the Copley Mall, Northeastern University, and Fenway Park. The hotel has a rooftop pool, although it won’t be open in the winter. ($150+)
The Omni Parker House is a historic treasure in Boston. It’s the home of the Boston Cream Pie and Parker House Rolls, so be sure to check out the dining options in the newly renovated hotel located right on the Freedom Trail. ($119+)
Another great choice just off the Boston Common is the Boston Park Plaza Hotel. Newly renovated, the hotel features a Starbucks next to the lobby, an attached gym, places to grab a quick bite to eat, and a steakhouse. ($108+)
The Boston Seaport Hotel is close to popular attractions like the New England Aquarium, Quincy Market, Faneuil Hall, and the ICA Boston. ($150+)
The Liberty Hotel is ironically a former prison, and they’ve kept some historic touches such as intact exterior barred windows and original brick. Their in-house bar and restaurants, Clink and Alibi, are named as throwbacks to the hotel’s time as a city penitentiary. ($168+)
Yotel Boston is located in the Seaport, making it a convenient and affordable option for budget-conscious travelers. The small rooms are sufficient for sleeping and seem to be most comfortable for solo travelers. ($105+)
Found Hotel on the Boston Common is a fairly new addition to the Boston budget hotel scene. The location can’t be beat, and breakfast is included! ($66+)
Hostel International Boston (HI Boston)
HI Boston is located in the Theater District, making it a great place to explore the Boston Common and Chinatown. It also has easy access to the South Station MBTA stop / bus station. Rooms are shared, but the hostel is clean, and breakfast is included! ($55+)
One of the very best things to do in Boston in the winter is to visit one of the amazing museums. The Museum of Fine Arts (MFA) Boston is host to an incredible year-round collection, as well as exceptionally curated visiting exhibits. Visit during a First Friday of the month for late-hours, cocktails, mingling, and music. Regular admission is $10 for kids and up to $25 for adults.
Just down the street from the MFA Boston is one of the most-loved Boston museums, the Isabella Stewart Gardner Museum (ISGM). The Isabella Stewart Gardner Museum was founded in 1903 by Isabella Stuart Gardener, an eccentric widow who dictated in her will that the exhibit locations must remain unchanged after her death. She carefully placed each item in the museum in its place where it has remained ever since. You can’t miss the gorgeous courtyard with its rotating display of trees, flowers, and greenery. They also host concerts in a contemporary music hall in the new wing of the museum. Admission is $10-$15.
If you want to skip fine art, head to the Museum of Science where you can find a 65-million-year-old Triceratops fossil, explore the inside of the human body, take in one of their rotating special exhibits, and explore the skies in the Charles Hayden Planetarium. Admission is $8-$28.
I just love the New England Aquarium. It’s located right on the Boston Harbor and is easily accessible by the Aquarium T stop on the Blue Line. They are one of the best marine conservation aquariums in America, and in addition to the caring for a host of marine life, they also offer public programming and talks on conservation efforts. Admission is $19-$28.
The Institute of Contemporary Art is a must-visit museum if you’re into modern art and find yourself in the Boston Seaport neighborhood. The collections are carefully curated, and the museum looks out over the Boston Harbor where you can see the airport in the distance. Admission is $10-$15.
I recently went to the Boston Children’s Museum for the first time for a special event and was blown away with how big and fun it is! Kids would love to spend a day here at this Boston museum playing in all of the exhibits over three floors. They also offer tons of winter-specific programs for chilly Boston winter days. Admission is $17 but the TJX Company sponsors $1 Fridays after 5pm.
If you have a few days to look for things to do in Boston in winter, you might want to consider the Go Boston Card. You can purchase the card for day increments of 1, 2, 3, 5, or 7 days, and it gives you free admission to over 40 museums and attractions (including all of the museums I listed above! You also have access to the “Hop on Hop off” bus, which will keep you from waiting outside too long for a city bus between things to do.
Just listing a few options for entertainment in Boston is going to be difficult! We are so lucky to be host to a number of first-class theaters, orchestras, sports teams, and clubs that you’ll find no shortage of Boston entertainment options. But here’s a short list of a few of my favorite places for winter entertainment.
The Wilbur Theater presents some of the best new and established comedians like Colin Jost, Adam Carolla, Norm MacDonald, Amanda Seales, and other hilarious acts.
The Boch Center presents a variety of touring and local productions in their grand Wang Theatre which holds about 3,600 seats, and their smaller gem of a theater, the Shubert Theatre, which seats about 1,200. They present a variety of nationally touring productions like Dancing With the Stars Live, Kacey Musgraves, or Mariah Carey in Boston; and local performances like the Urban Nutcracker.
The Boston Opera House is home to Broadway Across America which presents touring Broadway productions like Charlie and the Chocolate Factory, School of Rock, and most recently, the Boston tour of Hamilton. This is also the home of the Boston Ballet’s performances.
The Celebrity Series of Boston is a Boston performing arts powerhouse, presenting over 50 events each year in classical music, dance, jazz, and speakers. Their illustrious roster of performances from October to May include artists like the Alvin Ailey American Dance Theater, author David Sedaris, cellist Yo-Yo Ma, Broadway and television star Audra McDonald, songstress Renee Fleming, and other world-class artists. They also offer free and low-cost concerts in Boston neighborhoods.
Boston Ballet offers a number of story ballets and contemporary programs annually in the Boston Opera House. The professional company also offers its classic Nutcracker every November and December in time for the holiday season!
The Boston Symphony Orchestra performs weekly concerts with it’s world-class, Grammy-winning ensemble led by music director Andris Nelsons. They frequently host guest artists and conductors like Gustavo Dudamel, violinist Lisa Batiashvili, or pianist Yuja Wang. Their Holiday Pops concerts are a fun way to kick off the holiday season with a visit from Santa and an audience singalong!
Catching a play is one of the best things to do in the winter in Boston. We are #blessed to be home to a number of outstanding theater companies like Speakeasy Stage, the Lyric Stage Company, and the Huntington Theatre Company.
If you’re a sports fan, you will want to pay a visit to a Boston Celtics or Boston Bruins game. Both teams play at the TD Garden, which is right next to Boston’s North End. Grab some pizza or Italian food in the North End before catching one of the games.
The Boston Common Frog Pond ice skating rink was voted as the #2 outdoor skating rink in the country by USA Today! You can rent skates and ice skate right on the Boston Common! Admission is $6 and rentals start at $6.
If you’re looking for a fun night out in Boston with dancing or live shows, check out Royale Boston nightclub and concert venue, or the House of Blues Boston. Both offer celebrity performances like The Roots or Dropkick Murphy’s with a full bar and plenty of space to dance.
I’ll be covering a bigger list of bars and restaurants later in this article…keep reading!
I also wanted to put together a winter packing list for Boston for you. While the winters can sometimes be mild, more often than not you’re going to be facing freezing temperatures with gusty winds, ice, and snow. I’ve found that show can be heaviest in February and into March, and the cold weather can easily last into April. So I hope this packing list of what to wear in Boston in the winter can help you not freeze your buns off.
You’ll likely need a winter parka that is wind and water resistant. It will need to combat snow and freezing gusts, so pick one like this North Face Gotham Down Parka ($229).
I love wool since it is naturally water resistant and breathable. Check out mittens like these SmartWool Mittens ($32) or fleece lined gloves like these North Face ETIP gloves ($45) if wool isn’t your thing.
I have one of these Uniqlo down vests (link for men’s) ($49) which packs down into its own bag. It’s great for traveling since you can easily store it away in your day pack or purse if you get too warm.
Keep your neck warm with a scarf like this pretty and soft Prana scarf ($35).
I always wear sunglasses in the winter to prevent wind and salt from getting in my eyes when walking outside. The low winter sun is also insanely irritating when driving, so pick up a pair of RAENs sunglasses ($54+) which come in a variety of lens and frame colors.
Back to Uniqlo. I really like their Heat Tech leggings ($15+) which you can wear under dresses or sweaters, or layer under jeans for extra warmth. They also sell a fleece-lined version of their leggings (also $15), which are super soft and cozy for walking around outside or just hanging around your hotel. Men’s long johns are also perfect for guys to wear under jeans or pants ($20).
Don’t forget your feet in the cold! If you wear thin boots or sneakers, your feet will freeze. Pick up some Smartwool socks ($20) to keep your feet warm and dry as you sight see.
If you’re coming to Boston in the winter, you need to be prepared for the very real fact that it might be snowing, icy, ice raining, ice hailing, or generally cold as a mother. One time I slipped on a patch of ice on a sidewalk, fell, and bruised my tailbone for months because I wore regular shoes in the winter. Invest in a good pair of comfortable winter boots with some tread on the bottom so you don’t slip and fall in the ice and snow. Don’t be me.
Some of my favorite winter boots include these Columbia Omni Heat boots ($105); I have a similar version of them in blue.
I so wish I had packed some of these 10-hour hand warmers ($23 for 80) during my recent trip to Denmark. If you think you’ll be walking outside a lot in Boston in the winter, grab a few packets of these to keep in your gloves, pockets, or shoes.
Bring a sturdy day pack or backpack with you to hold all of your snacks, water, layers of clothes, sunglasses, and more. This travel backpack is a roomy option with a padded sleeve for your laptop or tablet, as well as a USB travel charging port ($35).
It gets extremely (wicked) dry in Boston, so pack some hand cream to keep your paws hydrated. CeraVe Therapeutic Hand Cream for Dry Cracked Hands ($7) is made with Hyaluronic Acid and Niacinamide to retain moisture.
Same re: dry air and cracked lips. Pick up this 3-pack of Sun Bum lip balms with SPF 30 ($8) and put one in your pocket, day pack, and in your toiletry bag.
Maybe you brought a special guy or gal to Boston with you and are looking for some unique date ideas.
Consider a winter photo shoot by one of the talented photographers on AirBnB so you’ll have a photo keepsake of your trip to Boston! I did this in Paris and it was 100% worth it for amazing photos and memories.
You can also cozy up with a hot chocolate in Boston; check out my guide to the top places for hot chocolate in Boston.
Since we’re on a chocolate kick, head over to the Taza Chocolate Factory in Somerville for a tour and tasting of their stone-ground chocolate.
Or, check out Improv Asylum in the North End if you want to laugh off all the calories you just consumed at one of the North End’s legendary Italian eateries.
Try a cooking class at the Boston Center for Adult Education (BCAE) in the Back Bay. They offer classes in preparing Italian, Indian, and Mexican cuisines, baking, and celebrity chef workshops. Go home with a new skill and avoid the cold weather at the same time!
One of my favorite things to do in Boston in the winter: SHOPPING!
If it’s not too cold, walk down Newbury Street to browse the high-end retailers and window shop for gorgeous gowns, shoes, and custom-made clothes. Newbury Street also has some excellent consignment shops for designer goods. You can grab a coffee at one of the cafes like the Nespresso Café or Tatte, and sit down for lunch or dinner at a number of restaurants. Some of my favorite shops on Newbury Street are the Uniqlo clothing store, Athleta for workout clothes, and Patagonia for warm-weather gear.
Just down the block from Newbury Street is the Prudential Center, and damn they have stepped up their shopping game lately. You can find a brand new and gorgeous Eataly with Italian cuisine. You can sit down and eat, take food to go, or shop at their grocery for cured meats, delicious cheeses, honey, and sweets.
You’ll also find a new Sephora, and Under Armor, Lord & Taylor, and Microsoft Store in the Prudential Center.
You can easily spend a few hours shopping and eating at the Prudential Center, and don’t miss going up to the Top of the Hub for a cocktail so you can catch panoramic views of Boston!
Attached to the Prudential Center by a sky walk is the Copley Mall, filled with dozens of high end retailers like Barney’s, Chanel, Burberry, Tiffany & Co., and Dior. It’s worth a visit just to ogle the gorgeous clothes and accessories.
Downtown Crossing shopping is experiencing an amazing resurgence. It’s filled with fun shops like Macy’s, a three-level Primark, an Old Navy, DSW, TJ Maxx, Marshalls, and Home Goods. If you’re heading to Downtown Crossing or the Theater District, leave some time for shopping. You might just leave Boston with an extra suitcase!
The Boston Seaport is bursting with hip-ness, and their shopping scene is exploding with trendy stores like a Fjallraven, pop-up shops by local designers, and an L.L. Bean outpost. Perfect for stocking up on your winter gear!
Just off the Orange line in Somerville is Assembly Row, an outdoor mall, restaurant, and entertainment complex. You can easily spend an afternoon strolling through all of the shops, having a Mike’s Pastry, catching a movie, or walking along their Riverfront.
I know you’re on vacation, but sometimes it’s nice to try workout classes in a new city! And isn’t it just delicious to leave a toasty yoga class after walking around all day? Plus, if you’re like me, you’ll need to burn off mad calories after stuffing yourself on all the delicious food Boston restaurants have to offer.
Before my hip surgery, I used to love trying so many Boston fitness classes. Here’s a quick list of some of my favorites.
Try Peter Welch’s Gym for an authentic Southie boxing experience. This no-frills boxing gym offers tough group classes that will leave you drenched but exhilarated after endless rounds of bag drills, squats, and sprints.
Check out Pure Barre on Newbury Street for a classic barre class to tone your entire body. The studio is modern and clean, and overlooks Newbury Street. Hit up a class after shopping!
I love Exhale for their yoga (and barre) classes. Exhale has two studios in the city, but the one located right off the Boston Common is the most convenient, in my opinion. After class, take advantage of their locker room amenities and showers before you head back out!
I go to Upward Spiral Pilates in Cambridge, and I love their mat classes. Also check out the reformer classes at BTone. They will seriously kick your butt and leave you with a booty and ab burn for days.
As a former Spin instructor, I am a purist when it comes to group cycling classes. My favorite studio is Flywheel in the Prudential Center for their excellent instructors and first-class gym amenities like showers, towels, and toiletries.
TrillFit in Downtown Crossing offers empowering and fun group dance and sculpting classes for all levels set to hip hop and pop hits.
Kelly Brabants is a Boston fitness instructor who is turning her legendary Booty By Brabants fitness classes into an empire with a line of flattering fitness-apparel. Her classes are so fun and uplifting, and you’ll leave with an incredible leg and booty burn from the hour of toning drills. I hope to get back to a class after my hip is all healed up!
Boston has really upped its game with a number of fun restaurants and bars. Across all price points, you can find quality dining experiences for all cuisines.
Some of my favorite spots for brunch in Boston are The Friendly Toast for their inventive menu, Club Café for their buffet brunch with endless options, Aquitaine for French-inspired omelets and pastries, and My Diner in South Boston for hearty portions. The Langham Hotel offers a chocolate bar on Saturdays, complete with a donut wall and warm cookies.
For lunch and dinner, some of my favorite Boston restaurants are Eventide Oyster Co. for their fresh oysters and seafood, Kashmir for Indian food on Newbury Street (their creamy chicken Tikki masala is to die for), Deuxave for when you really want to splash out on a nice night out, and Montien for Thai food. Boston Chinatown has an amazing selection of Asian restaurants like Hei La Moon for Dim Sum and Tea Do for bubble tea. And how could I neglect mentioning Chicken and Rice Guys in the Theater District? Its Boston location rivals their famed NYC food carts.
For seafood in Boston, you can’t go wrong with a visit to one of the Legal Seafood locations. Try their clam chowder with the house rolls to start—Divine! There’s a new lobster joint in the Back Bay near the Prudential Center called Luke’s Lobster where you can eat at a shared indoor patio table or bar or take your lobster to go.
My favorite steakhouse in Boston is Ruth’s Chris Steakhouse, and now they have three Boston-area locations! There’s one in downtown Boston just steps away from the Boston Common, one in Waltham, and now there’s a brand new location in Assembly Row in Somerville. (Assembly Row is a great destination for a movie or shopping, too!) You can’t go wrong with one of their mouthwatering steaks and sides like mac and cheese.
For the best Boston bars and nightlife, check out the Hawthorne near Fenway Park for their inventive cocktails and top-notch bartenders. If you like tequila, Masa in the South End has a full tequila bar and delicious Mexican bites. I also recently checked out Dona Habana in Boston, and was super impressed with their vast cocktail list (just the types of Mojitos was a full page long) and outstanding Cuban food.
For beer in Boston, pay a visit to the Samuel Adams Brewery in Jamaica Plain, where you can tour the brewery and taste some of their beers.
Tipping is generally expected at any meal you eat in a sit-down establishment. This includes bars, too. It is standard practice to tip 15-20% on the amount of your bill before taxes, and $1-$2 for each drink you order at the bar.
My sincere wish for you is that during your visit to Boston the subway/MBTA works. When it works, it’s going to be a fast and cost-effective way to navigate the city. When it’s broken or on fire (not kidding), just grab a taxi or Uber.
But let’s say it’s working. The MBTA (or also called the T) consists of four rail lines (Red, Blue, Green, and Orange), a Silver bus line which serves the Seaport, and the Commuter Rail which serves Greater Boston. (MBTA stands for the Massachusetts Bay Transportation Authority, FYI.)
Single rides are $2.75, and a week-long pass is $21.25 (this actually is a good deal if you take the T a couple of times per day). The passes work on both buses and the local rail lines. Commuter line passes cost a little more. Here’s a link with all of the MBTA prices.
Use one of the maps in each station to help find your starting, destination, and transfer points. Google Maps will also help guide you from door to door, including all transfers.
If you just want to Uber or Lyft, save $5 off your first ride with my code, linked here.
Check out my other city guides!
Hey there, I am Stephanie, aka “The Roving Fox!” I started this blog to share travel tips with friends, and eventually started incorporating more info about my hip labrum surgery, beauty products I love, and restaurant reviews. Please say hi here on the blog, on Instagram, or Facebook!
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