The 20 best things to do in Boston

What is it? Take to the frozen hills of Boston with your trusty sled and fulfill the need for speed on snowy Flagstaff Hill in Boston Common, Peters Hill at Arnold Arboretum, the Sugar Bowl in JP, Olmsted Park, Franklin Park, and Dorchester Park, to name a few. 

Why go: Pack some hot cocoa in a Thermos and enjoy quite a winter wonderland. 

What is it? You've done a little exploring of Boston on the ground, now see what it looks like from high above at View Boston, a stunning observatory that takes up the top three floors of the iconic Prudential Tower. (That's 52 stories up!) 

Why go? The immersive attraction offers visitors a personalized perspective on the city, with interactive displays featuring tidbits about Boston art, music, history, neighborhoods and more.

Don't miss: Head out to the Observation Deck to see 360-degree views, then grab a drink at Stratus, Boston’s highest rooftop bar. They have a gorgeous Winter Bar set up, covered in twinkle lights and seasonal splendor. 

What is it? With some essential Boston experiences under your belt, consider hoping across the Charles to spend a day in Cambridge, where an excellent day of shopping and Ivy League campus-peeping await. 

Why go: Cambridge is made up of a collection of squares, all of which offer an excellent selection of thrifts shops, home goods stores, ice cream shops, restaurants, dispensaries, bars and more. The uninitiated can get a perfect overview walking along Massachusetts Avenue between Central and Harvard squares, where the vibe is more Haight-Ashbury than Ivy League. 

Don't miss: Dinner! Cambridge is home to some of the very best restaurants in Boston. Try Judy's Bay, a hip haunt for Japanese. Puritan & Co. offers an updated spin on traditional New England fare. Urban Hearth sets a standard for farm-to-table restaurants everywhere.  

What it is: Every year, the Frog Pond in the Boston Common opens up as an outdoor skating rink. Whether you bring your own or you rent skates, taking a few spins around the ice is probably the most Bostonian thing you can do. They even offer ice skating lessons. 

Expect to pay: Admission is $12 for 58 inches and over, and free for under. Skate rentals are $12-$18.

Opening hours: Sun., Tues.-Thurs. 10am-9pm; Mon. 10am-3:45pm; Fri. and Sat. 10am-10pm

What is it? The Boston Public Library (BPL) contains approximately 19 million volumes and electronic resources, making it the second-largest public library in the U.S.—coming right behind the Library of Congress.

Why go? At nearly 1 million square feet, the main branch in Copley Square impresses in a way that few libraries can. The original structure, designed by Charles McKim and completed in 1895, now serves as the research library, while an extension (opened in 1972) functions as the general library. Talks, performances and tours delight culture vultures from near and far.

Don’t miss: At the center of the library is a cloistered courtyard, one of the city’s most beautiful, tranquil places to read a book.

Want to see more in the area? Book a tour. 

What is it? One of the coolest streets in the world, Boston’s version of Fifth Avenue is perfect for both shopping, dining and people-watching.

Why go? Between Arlington Street and Massachusetts Avenue, there are eight blocks of beautiful brick townhouses housing anything from ultra-luxe designers and chic boutiques to affordable international chains. With a never-ending assortment of galleries, salons, cafés, bars and eateries to explore, you can easily spend an entire afternoon browsing, relaxing and indulging here.

Don’t miss: Fans of architecure and home decor shouldn't miss a stroll through the four floors of Restoration Hardware, which is housed in the gorgeous former home of the Museum of Natural History. 

Need some guidance? Book a tour that includes Newbury Street. 

What is it? Located inside the Mary Baker Eddy Library, the Mapparium is essentially a three-story model of the globe built to scale. 

Why go? This colorful sphere runs 30 feet in diameter and can be crossed by means of a glass bridge bisecting its interior. Inside, sound bounces off the room’s rounded walls, amplifying it tenfold, so keep in mind that there are no secrets in the sphere—no matter how softly you may whisper.

Don’t miss: The 608 stained-glass panels recreate the world as it was in the mid-1930s, when the project was completed. So keep keen eyes on those outdated borders.

Save money on tickets with a Go Boston Pass

What is it? New England’s largest aquarium and one of Boston’s most popular attractions.

Why go? More than 80 African, rockhopper and little blue penguins live in the New England Aquarium’s first-floor display. Watch them go wild during feeding time in front of the Giant Ocean Tank, a massive coral reef exhibit that's home to a myriad of other marine creatures, including sharks and loggerhead sea turtles. The building is designed in such a way that the penguins can be seen from multiple vantage points. 

Don’t miss: Be sure to say hi to the harbor seals in their enclosure outside, which is free and open to the public.

What is it? Boston's most magical holiday tradition is back - and bigger than ever. Winter Fest 2025 returns to Charlestown's Hood Park this December, transforming The Yard into an immersive, family-friendly winter wonderland filled with sparkling lights, local food favorites, rides, and festive experiences for all ages.

Why go: Running on select weekends from Dec. 6-7, 12-14, and 19-30 (closed Dec. 24 & 25), Winter Fest has been completely reimagined for 2025 with new attractions and a refreshed layout designed to capture the magic of the season. Guests can enjoy immersive amusements, carousel, carnival-style games, and an expanded winter market featuring local artisans, treats, and interactive activities - plus highlights like the Après Ski Veuve Clicquot Gondola Lounge, life-size ice castle, and weekend visits with Santa.

Don't miss: Tickets are $5 per person and include three hours of free parking at Hood Park.

What is it? From Dec. 5-21, the historical Mount Auburn Cemetery (America's first garden cemetery) in Cambridge becomes one of the region's most visually arresting winter experiences with its annual event, SOLSTICE: Reflections on Winter Light.

Why go: Beloved traditions returning include the candle lighting ceremony, lantern-lit pathways, and messages boards that foster quiet reflection amid the winter night. 

Don't miss: There will be 13 nights of artistic discovery and connection with nature with new installations. Bigelow Chapel will debut two new sound and animation works inspired by the natural rhythms of the solstice, while Hazel Dell transforms into a "cosmic stage" featuring a projection charting the life of a star. Along Beech Avenue, a new 300-foot illuminated artwork will weave trees, light, and sound into a dynamic, walkable experience.

What is it? Given the area’s renowned reputation for the sciences, it’s no surprise that Boston has a bevy of talented mixologists.

Why go? Why go out for a simple beer when you can order an immersive sensory experience in a glass? For a truly mind-blowing cocktail, head to local trailblazers like Farmacia and Equal Measure (which was just named a best bar in North America), both of which offer an expansive list of truly unexpected sips.

Don’t miss: For a next-level experience, try cocktails featuring house-made tinctures and shrubs at Parla. The North End spot even offers a dice game that lets you gradually unlock a secret drink menu.

What is it? The local collection of cozy, welcoming Irish pubs like The Burren and The Druid all but guarantee a lively night of craic. 

Why go? In a city chock full of proud Irish expats and Irish-Americans, it’s little wonder why Boston is brimming with an excess of quality pubs. To get the full experience, head in on a spirited trivia night, or during a live performance of authentic Irish music.

Don’t miss: For a centrally located option with nightly live tunes, look no further than the Black Rose.

What is it? There are many opportunities to laugh your socks off this season at one of Boston's veteran comedy clubs and other venues. The Improv Asylum in the North End has a loyal following, especially when it comes to the more risque late-night shows.

Why go? Some of America’s most popular contemporary comedians like Conan O’Brien and Bill Burr honed their craft in Greater Boston.

Don't miss: Think you have what it takes to crack some jokes for a crowd? Consider one of the improv classes at Improv Asylum this spring. 

What is it? The food hall trend is strong in Boston, with a wealth of them thriving around the city.

Why go? Offering numerous cuisines and drink options all in one spot, food halls are a great choice when you’re dining with a group—there’s something for everyone. They make for a great anytime meeting spot; just show up and see what kind of mood you’re in.

Don't Miss: Eataly is a haven for Italian food enthusiasts. The Boston Public Market is a quaint visit with fresh produce, cheeses, prepared foods and even home goods. And Time Out Market Boston showcases the best of the city under one roof. 

What is it? A little slice of Las Vegas in New England, Encore Boston Harbor is a mega-casino resort just outside the city in Everett.

Why go? The 210,000-square-foot complex—which cost nearly $3 billion to build—includes 15 high-end dining and lounge venues, an ultra-premium spa and more than 600 guests rooms for the ultimate staycation. 

Don't miss: Newest on the dining scene is seafood-centric Seamark.

What is it? Although quite splendid during the late fall and early winter month, the confines of the city can sometimes be a bit...much. Why not take the road head to a unique destination for a weekend away?

Why go: Head north to a luxury boutique hotel like The Weston in Vermont's Green Mountains for a snowy take on the season, or buck the system and go down the Cape (gasp - during the winter?) for a quiet escape to Chatham Bars Inn sans beach crowds.

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Music, art, food, nature and the year’s biggest parties—these are very best things to do and see right now, anywhere in the world.