Boston in winter affords many pleasures and unique opportunities for exploring the historical city. Writer Meryl Pearlstein shares some ideas with RealFoodTraveler.com readers for places to eat and drink, take in culture, and things to do. 

Save this article about things to do in Boston in Winter to Pinterest to help you plan your trip. Photos by Meryl Pearlstein. Graphic by RealFoodTraveler.com.

A Winter Getaway to Boston: A Trip Rich in History and Culture

For a long weekend that’s full of culture, great eats and history, Boston should be on your list for travel. But, why winter would you ask? The answer is simple: it’s less crowded than in height of leaf peeping season, and less frenetic than college move-in weeks or the Christmas holidays. And Boston is remarkably easy to navigate without a car, even if it’s snowy.

The shoulder season seems less of a shoulder season now – there’s much to do both indoors and outdoors, great deals to be had, and fewer lines to contend with. So pack your carryon, bring a few extra layers and maybe some long underwear, book your flight to Logan Airport or a seat on Amtrak, and let’s visit the capital of Massachusetts.

Things To Do In Boston in Winter

History fans are drawn to Boston to learn about Paul Revere’s historic ride, the Boston Tea Party (now celebrating its semiquincentennial anniversary at the Boston Tea Party Ships and Museum), and the most recent historical additions to the city, the Big Dig and the Leonard P. Zakim Bunker Hill Memorial Bridge. You can trace your own route along The Freedom Trail, following the red line emblazoned on the sidewalk that passes by 16 historic sites such as the 1660 Granary Burying Ground where Paul Revere, John Hancock and Samuel Adams are interred. Continuing on to Faneuil Hall, Paul Revere’s House, Old North Church and Bunker Hill Monument, you’ll refresh your learning about the beginnings of the United States. For a look at Boston’s pre-Civil War African American community, The Black Heritage Trail® celebrates locations like the 1805 African Meeting House and the 1835 Abiel Smith School important in the abolition movement which centered in Boston’s Beacon Hill in the mid-18th century.

The Freedom Trail winds its way through historic Boston.

If art is more to your liking, Boston is rich in museums such as the acclaimed Museum of Fine Arts with its collection of nearly half a million objects, the Isabella Stewart Gardner Museum set in a lovely palazzo, and the cutting-edge ICA (Institute of Contemporary Art) which also enjoys a stunning view over Boston Harbor. Across the Charles River in Cambridge, the world-famous Blaschka Glass Flowers at the Harvard Museum of Natural History are perennial attractions with their hand-blown artistry.

Boston has a fascination with outdoor art as well as indoor exhibits. You’ll see installations throughout the city, changing at various times during the year. In the summer, the Cow Parade took over the city with 75 life-sized, painted cows sold to support The Jimmy Fund and the Dana-Farber Cancer Institute. The Seaport and harbor area have a variety of changing sculptures and pieces, some interactive, some just reflecting the culture and colors of the city. The Embrace, by Hank Willis Thomas, Boston’s newest permanent sculpture, sits proudly on Boston Common’s Freedom Plaza and is a memorial to the love between Dr. Martin Luther King Jr. and Coretta Scott King who met in Boston.

“The Embrace” sculpture, by Hank Willis Thomas.

This winter Canada has invaded Boston, bringing a wry sense of humor to art activations throughout the city. Winteractive is an art experience in Downtown Boston inspired by the winter festivals and art exhibitions in Quebec. You’re encouraged to look up, peer inside, and turn wheels to appreciate these somewhat-crazy art pieces. From a free-floating heart reeled in by a fisherman sitting on the edge of a roof, to oversized clown faces jammed between buildings to boxes that play music when you turn their cranks, the city has become an art playground this winter.

Discover art in unexpected places in Winteractive like this “Endgame.” Photo by Annielly Camargo.

The Bruins are the ticket in the winter in sports-crazy Boston and even if you don’t get to watch a home hockey game, you should plan a visit to The Sports Museum at TD Garden. All teams receive their due here from Boston’s beloved Red Sox and Celtics to the Bruins and the Patriots. You can also schedule a tour of Fenway Park with the opportunity to sit on the Green Monster and or in one of the press boxes – just dress warmly as quite a bit of the tour is outdoors.

Part of the baseball exhibit at The Sports Museum in Boston.

Meandering along shop-filled Charles Street at the foot of Boston Common, past luxury stores on beautiful Newbury Street, or to the most photographed spot in Boston, cobblestoned Acorn Street can quickly add to your step count while providing some challenging hills. You can also stop to visit the varied outdoor art installations in the Seaport or take a shot at curling at Snowport, Boston’s Seaport turned winter wonderland. Winter in Boston encourages you to stay and play outdoors!

Buy a CharlieCard for an economical way to cover the city’s varied neighborhoods on the “T,” Boston’s subway with its trolleys and trains. To understand why the pass is so-named, google “Charlie on the MTA” and listen closely to the lyrics. For those who prefer walking, you can plan a route that travels through the city’s numerous parks from the Public Garden where Nancy Schön’s famous Make Way for Ducklings statues make their home, across the street to the Boston Common (once the home of grazing cows), to the Rose Kennedy Greenway, a string of green parks that extends from Faneuil Hall to the Seaport. For a lesser-known, beautiful hike, the seven miles connecting nine parks known as Boston’s Emerald Necklace were designed by landscape architect Frederick Law Olmsted of New York’s Central Park fame. The parks are connected by parkways and waterways and will give you a look at a variety of neighborhoods from Boston to Brookline.

Nancy Schön’s famous Make Way for Ducklings statue.

Hungry for more? Welcome spring in Boston.

Where to Stay in Boston in Winter

Take advantage of the off-season rates at the luxurious Newbury Boston overlooking The Public Garden. The hotel has been the site of a variety of top-rated properties over the years including the Ritz-Carlton and The Taj, but in its current reincarnation as The Newbury, the luxury quotient has truly been amplified. The lobby has been reoriented to allow for optimum guest flow with marble floors and two entrances, one on Newbury Street and the other directly facing the park from the popular Street Bar.

Splurge on a fireplace suite for the ultimate indulgence. You can cozy up around the coffee table in front of the fireplace with a glass of Champagne as you take in the views of Boston Common and Back Bay from above. Your fireplace butler will assist in setting everything up for you. Luxury appointments include original artwork, custom-designed furnishings and luxurious robes and linens. Room service is available at all hours, so if you’ve exhausted yourself soaking up Boston’s extensive history or art, you won’t have to go far to enjoy some New England treats. The hotel’s concierge will also make sure that your every need is met from obtaining hard-to-score Bruins tickets or a box at the Boston Ballet.

The Newbury offers dining in two restaurants. The ground-level Street Bar is a casual eatery and lounge with an adjacent cozy Library space. Grab some local oysters on the half, spicy pink lobster chowder and maybe a local favorite, pigs in a blanket, here baked with Wagyu beef in the center. Pair them with the specialty Newbury 75 cocktail and enjoy the clubby setting.

Book well ahead for lunch or dinner at gorgeous Contessa on the roof. The glass-enclosed restaurant fronts on both the Public Garden and Back Bay, for the ultimate in dining with a view. Italian dishes feature here with memorable and unusual dishes like squash carpaccio, a silky combination of thinly sliced squash with pumpkin seeds and sweet-and-sour agrodolce. It’s one of those dishes that you’ll remember for a long time. The menu rambles from seafood to meat, pasta to pizza, with everything prepared with the perfection that you would expect from a Michelin-starred eatery. I have my heart set on Contessa’s signature Bistecca Fiorentina for my next visit, with, of course, the squash carpaccio. If you miss out on lunch or dinner, Contessa happily serves breakfast and has a beautiful bar so you won’t miss out on this experience.

Squash Carpaccio is one of Contessa’s popular and creative dishes.

Hungry for more? Discover a springlike place to stay in Boston.

More Great Eats in Boston

While Contessa should be at the top of your list to reserve in advance, more impromptu dining can be had at the always-fun Time Out Market at 401 Park. There, 16 concept stands offer a range of cuisines like Boston’s iconic roast beef sandwiches (you can’t find them anywhere else) tacos, pizza, and another Boston staple, donuts. Depending on the temperature, you might want to rent a pair of skates to work off your meal on the outside rink. Not your thing? Trillium Brewing Company offers a nice choice of brews and you can watch the skaters while you relax. High Street Place brings you to the heart of downtown with 20 vendors where you can graze from seafood towers to tacos washed down with a craft beer from the creative Alewives Taproom.  Also downtown, Boston’s newest food hall, The Lineup by New York Chef John Fraser, offers a choice of California-influenced Mexican cuisine, pizza, vegetarian burritos and Mediterranean dishes.

Enjoy a variety of food from different vendors at Time Out Market.

Boston dining offers much more than seafood, but you’d be remiss if you didn’t indulge in at least a few aquatic options. Your choices range from fine dining where no bibs are required but dressing up is encouraged to lobster shacks floating on boats or planted on the ground. Legal Seafood’s three-story Legal Harborside in the Seaport offers a little bit of everything on its large pescatarian-focused menu. Enjoy the clam bar in a casual setting or opt for a fine dining experience with a menu from Legal Test Kitchen that includes elaborate seafood preparations like nori-chili crusted yellowfin tuna. For oyster lovers, Row 34 is a must. Set in a former warehouse amid the city’s burgeoning Fort Point area, Row 34 is the go-to for striking décor, oysters and unusual beers. The menu also offers a New England favorite, the lobster roll two ways, cold the way Bostonians prefer or hot as those from Connecticut favor. Tiny Select Oyster Bar in Back Bay has a changing daily menu of fresh bivalves if you find yourself in need of a shopping break.

Even Boston in winter means fresh seafood at Row 34. 

Boston’s Chinatown is a messy array of dumpling, hot pot and pho eateries but the most comprehensive Asian food menu can be found at popular Empire, a cavernous, striking restaurant in the Seaport. The menu roams from country to country with choices ranging from Korean bibimbap to Singapore street noodles and the lavish viper roll from Japan with unagi, sweet potato tempura, avocado and spicy rice crisp. The combination of flavors are sensational. Cocktails are fantastic, too – try the Pistachio Martini for dessert. Empire’s experienced servers will help you decipher the enormous menu. For more pan-Asian choices, The Nautilus on Pier 4 features small shareable plates divided into sea, land and garden categories. Nearby Ocean Prime adds a choice for surf and turf, with a solidly curated menu of steaks, sushi and lobster faves, along with cocktail whimsy. Get your video set for the “smoking” Berries & Bubbles in both spirited and non-alcoholic versions.

Empire’s decor is dramatic and a draw for the restaurant’s delicious food.

Boston’s North End is famed for its Italian pasticcerie and restaurants. Continue walking behind Faneuil Hall and the historic Union Oyster House (dating from 1826) to Hancock Street where you’ll find two bakeries worthy of your attention. Across the street from each other, the Modern Pastry Shop and Mike’s Pastry have been preparing cannolis, paraginas and baba au rhum for some 90 years. For dinner, pasta lovers have many fine choices including Trattoria Il Panino, set in a lovely townhouse on Hancock Street, the main street of the historic neighborhood. Friendly service and homemade zuppa di pesce will warm you up along with a glass of limoncello. If you’ve never seen the term sfizi on a menu, you will here. It correctly refers to the chef’s whims and unusual choices that you’ll see presented. Come hungry and try a few! Thin-crust, spicy-sweet sauced pizza reigns supreme at Regina Pizzeria, the choice of Bostonians since 1926. For a romantic evening, Mamma Maria will wow you with gracious service and traditional foods in a myriad of small rooms in a historic building across from the Paul Revere House. If you haven’t had a chance to visit the Union Oyster House, return there for dessert, a slice of iconic Boston Cream Pie.

A Day Trip from Boston: More Things to Do

Set your sights north of Boston to the state’s toniest coastline area, the North Shore. Take the MBTA train from North Station to historic Salem, now that the Halloween masses have gone. You can fill your day with sorcery and 17th century history with visits to the House of the Seven Gables, the Salem Witch Museum and The Witch House, home of the judge notoriously involved in the sentencing of local girls accused of witchcraft. For a nautical dining experience, head to Pickering Wharf where local favorite Finz offers traditional New England baked halibut, lobster rolls and clam chowder along with “new-fangled” sushi creations.

Hungry for more? See where to get immersed in the Salem Witch Trials.

You can also rent a car for a one-day tour along lovely route 127. Most of the drive from Salem to Cape Ann hugs the shore, leading you to the quaint fishing town of Gloucester and its beautiful Rocky Neck art colony. There, stop and take a photo of the famous fisherman statue staring at the cold Atlantic Ocean. Is he thinking about what he’ll catch that day, or whether he’ll make it back home? You decide. The Gloucester Fishermen’s Wives Memorial monument sits nearby, depicting a woman with two children worriedly looking out to sea as they wait the men’s return home. Pass through the town center and note the headquarters of Gorton’s of Gloucester marked by the sign of another fisherman. Nearby is Crow’s Nest where the movie fishermen from The Perfect Storm drank away their sorrows.

-Story and photos, except where noted, by Meryl Pearlstein

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