The 50 best things to do in Boston

The most heartening sign that spring is coming is the emergence of tiny flower buds all around the city. The Isabella Stewart Gardner Museum and the Arnold Arboretum take the enjoyment one step further in their annual springtime floral celebrations. Every April, the hyacinths that hang from the upper levels of the ISG’s garden atrium bloom for one month, displaying their vibrant orange blooms for winter-weary visitors. If lilacs are more your style, the Arnold Arboretum in Jamaica Plain boasts one of the oldest and largest collections of lilac bushes in the world, predating even the founding of the Arboretum in 1872. The Arboretum celebrates this fact every year with its annual lilac festival on the second Sunday in May, when thousands of people come to view the fragrant flowers in full bloom.

Every Wednesday night (weather permitting) Coit Observatory at Boston University opens up its facilities for free public viewings of the stars. The viewing starts at 8:30pm, lasts about hour, and promises to help you to distinguish your Andromeda from your Milky Way. If you find yourself at the Museum of Science on a cloudless Friday night, visit the Gilliland Observatory. Located on the museum's parking garage rooftop (romantic, no?), the observatory is equipped with a powerful computer-controlled telescope and staffed by employees who are happy to give you a free crash course in astronomy. It’s generally a good idea to call the observatory hotline beforehand for an update on the weather and a list of currently visible objects in the night sky.

The Freedom Trail isn’t the only historical walk in town. While the self-guided, two-and-a-half-mile tour provides a useful sightseeing starting point for newbies, graduate to these specialized rambles. The Black Heritage Trail traces the history of the African-American community in Boston in the late 18th and 19th centuries, the Women’s Heritage Trail comprises 10 separate, self-guided walking tours flung across various neighborhoods, and the Irish Heritage Trail takes in museums, statues and memorials celebrating everyone from “poet, patriot, prisoner, sportsman and orator” John Boyle O’Reilly to (who else?) JFK.

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There’s a lot more on the grounds of Harvard Yard than elite pupils and posing tourists. The iconic redbrick walls have contained some truly stunning stories, and a visit serves as a Who's Who of American history—alumni include John Hancock, JFK and Barack Obama, while Matt Damon, Bill Gates and Mark Zuckerberg are among the famous dropouts. The campus also features striking architecture designed by such luminaries as Bulfinch, Le Corbusier (his only U.S. building) and Sert. Each Saturday, three free student-led tours leave the Holyoke Center at 10am, noon and 2pm for a one-hour tour of the nation’s top university.

Now a Boston landmark, Symphony Hall opened its doors in 1900 as the home of the Boston Symphony Orchestra and the Boston Pops Orchestra. Extended in 1990 to include the Cohen Wing, it continues to update its facilities with new audio reproduction technology. Still, it's the all-important acoustics of the original interior design that have made it one the world's top auditoriums. In July and August, the BSO decamps to Tanglewood in the Berkshires, Western Massachusetts, which also hosts the Festival of Contemporary Music and the Tanglewood Jazz Festival.

Visionary landscape architect Frederick Olmsted liked Jamaica Pond, the centerpiece of the Emerald Necklace, for its "reflections and flickering half-lights." A stroll through the woods around the pond will clue you into what he was talking about. The best place to relax, though, might be on the water itself: Rowboats, kayaks and sailboats are all available for rent. If you’ve got a fishing license for some reason, bring your pole and your best Huck Finn smirk.

Stretching from Cambridge to Bedford, the 11-mile Minuteman Bikeway is a great way to check out Greater Boston’s outer boroughs. Built on a former railway, it’s open to biking, rollerblading, jogging, walking and more—anything sans motor, basically. There’s also plenty to see along the way, including Alewife Brook Reservation, Spy Pond and Arlington’s Great Meadows. Casual pacing is the name of the game, so speed demons should look elsewhere.

Whale-watching isn’t just for junior high school field trips. Hop on one of the boats that head out of Boston Harbor daily and rediscover how awesome it actually is to be within spitting distance of the largest mammals on earth. Bring a sweater and park yourself at the hull of the boat for the day so that you’re sure not to miss a second of the action. The snack bars aren’t the best, so make sure to pack provisions (you may want to leave the tuna fish sandwich at home, though). The boat's fully stocked bar is a plus.

Celebrate your right to thumb your nose at frustrated motorists as you blithely cruise down the double yellow on your in-line skates or sprint down the middle of the street pushing your baby carriage. Every summer, Cambridge poses the question “Why don’t we do it in the road?” and answers by blocking off Memorial Drive to automobile traffic along the Charles River on Sundays, and handing over the highway to pedestrians, bikers and Frisbee enthusiasts. And every summer, reams of distraught motorists forget this fact and pull up to the police barriers fuming audibly—which is all part of the fun.

In the summer months, the North End turns into a slice of old Italy as the local Italian community put on a number of feasts and festivals in honor of Italian saints. The streets fill with participants and bystanders alike, all watching the confetti fly, the banners sway and the processions make their way through the narrow cobblestone streets. While it may seem like every single Sunday is a cause for celebration, the biggest are the Fisherman’s Feast of the Madonna in mid-August and Saint Anthony’s Feast later that same month. Expect great food, boisterous crowds and statues covered in dollar bills.

Did you know that there are a number of awesome New England beaches just a short train ride away from Boston? Crane Beach can be reached by a shuttle bus that departs from the Ipswich commuter rail station throughout the summer, and also boasts some of the best wildlife-attracting salt marshes around. Singing Beach and Good Harbor Beach are also accessible by public transportation. If you’re not content with merely relaxing by the waves, hop on the train to Plum Island, where you can also explore the quaint seaside town of Newburyport—just keep an eye on the time so you don’t miss that last train home.

Bundle up, grab your skates (or rent them for $8) and take a spin in the middle of America's oldest public park—preferably on a clear, starlit night. Rink snobs need not worry: the Frog Pond is Zamboni-slick and has its own ice-making system. Pop over to Silvertone afterwards for a cozy booth, well-executed comfort food and some great cocktails that won't break the bank. We recommend the Joey Joe Joe Jr. Shabadoo, a potent blend of ginger beer and rye.

Each time you drink a glass of water in Cambridge, consider that it comes straight from this source. Located just under two miles northwest of Harvard Square, these 162 acres of open space feature a golf course, a butterfly meadow, woods, several ponds and a 2.25-mile perimeter road to walk, jog or amble around. Take note of the restroom at the Rangers’ station in case all that water has you feeling, er, inspired.

Remember when being able to jump the highest was a badge of honor? Bring back the kid in you at Sky Zone, a 10,000-square-foot indoor trampoline park near Dedham. It’s not just about getting air but also a cool way to hop out of that fitness rut via open jumps, “skyrobics” or 3D dodgeball. What’s more, the park offers plenty of slots in which adults can bounce about freely without having to worry about landing on a kid. Saturday night’s “sky jam” is reserved for 18+ and includes pizza, soda and 90 minutes of jump time for just $15. We recommend consuming the pizza and soda post-bouncing.

The Boston area sure has its fair share of districts—the Financial District, the Theater District, the Leather District, the Garment District (okay, that last one is a actually a store)—and Central Square in Cambridge has become something of an unofficial Dance Party District. A far cry from the Top 40 club-banging hotspots on the other side of the river, the hodgepodge of offerings on a few choice blocks of Mass Ave cater to a wide variety of tastes. Check out Eastern European electro-club fare at the Middlesex Lounge’s Make It New (Thursdays), the eclectic throwback and hip-hop nights at Phoenix Landing or the live soul and funk stylings of Cambridge’s own Chicken Slacks at the Cantab Lounge (Thursdays).

Boston’s favorite way to see Shakespeare is in the park, on a blanket and with a cup of something that totally isn’t wine (wink). So claim a grassy spot on the Common and check out the Commonwealth Shakespeare Company's near-nightly productions of the Bard’s best works from late July through the end of August. The company sets up its stage in the open air, and you can see costumed players running around and stage hands working their magic by the glow of the State House’s dome. Performances are all free and make a perfect summertime date or relaxing literary outing.

What began as a Lebanese eatery in 1970 has steadily grown into one of the city’s best locations for live music. Almost every night of the week, the Middle East club will crank out a show on each stage—Upstairs, Downstairs, and the Corner. Saturdays are especially busy, with frequent matinee concerts popping up on both the Downstairs and Upstairs stages. Each Saturday night, the complex’s fourth branch—the bar and restaurant ZuZu—hosts Soul-le-lu-jah, a funky throwdown fueled by classic soul tracks.

Candlepin bowling is a uniquely New England quirk—as the name suggests, the pins are tall and much thinner than those of ten-pin or duckpin, and balls are closer to softball-sized. For those seeking this fun, cheap and unconventional group activity, Sacco's at Flatbread Somerville is a frequent favorite. This oasis of TV-free, retro splendor uses paper scorecards, features a jukebox and has generally retained much of its character despite recent renovations. The place also serves organic pizza with eccentric toppings, plus an impressive selection of wine and local beer.

Chic wine shops like Central Bottle and Urban Grape offer regular tastings of their newest and/or best bottles. Wannabe oenophiles shouldn’t be intimidated by the insider-y gathering and swanky surroundings—both shopfronts aim to educate the uninitiated on wine-tasting and production—and send participants home with affordable bottles. Tasting times vary, so go online for the latest event listings.

In Boston, there’s a whole world of food truck cuisine just waiting to be devoured. Comfort food abounds: M&M Ribs (a.k.a. Big Moe’s) serves up barbecue with soul food sides, all packaged up as take-out in the corner of a deserted lot. The self-explanatory Roxy’s Gourmet Grilled Cheese sets up shop on Beacon Street and Chestnut Hill Avenue in Cleveland Circle. But there are healthy options, too. One of the crowned victors of the City of Boston’s Food Truck Challenge, Momogoose offers Asian cuisine (including an impressive list of curries, some vegan), plus a dessert bar. MIT-area favorite Clover Food Lab opened a couple of brick and mortar outposts recently, but the original iteration can be found parked in a lot on the MIT campus or in the Financial District’s Dewey Square.

Dim sum brunch at China Pearl is great all year round. The gigantic dining room is always packed no matter the weather, and the carts piled high with unidentifiable (but unwaveringly delicious) plates know no season. However, in the warmer months, Chinatown becomes more of a destination rather than simply a means to an end. Take a walk down Kneeland Street after you’ve eaten all you can, and stop by the multitude of Chinese markets that spring up on the corners. You’ll find everything from durian fruit to sardines stacked up for sale, and can easily spend a whole day wandering through the myriad shops lining the busy streets. If you’re feeling adventurous, stop in at Chau Chow City for its infamous “off the menu” selection of flaming drinks. Ask for the Flaming Ferrari to see what we mean.

J.P. Licks is a local institution, its branches scattered all over the city. The local chain is known for its funky atmosphere, hip scoopers and flavors so good they'll bring you to your knees, so expect to wait in line on hot days. A bit tougher to get to—but worth the trek—is Christina's Homemade Ice Cream in Inman Square. It’s a favorite among local restaurateurs looking to amp up their dessert menu with the shop's painstakingly crafted, beautifully realized seasonal flavors, which include fresh rose, burnt sugar and ginger molasses. Toscanini's is another Cambridge spot with out-there ingredients. The staff constantly labors to come up with new and interesting varieties like the salty bacon and the smoky sweet burnt caramel (which was invented by accident).

Get your fill of fried goodness at some Boston’s top donut shops, spanning the latest cult bakeries, pop-ups and under-the-radar mom-and-pops. The antithesis of mass production (sorry, Dunkin’!), the treats are lovingly made from the South End to Somerville. Stick with the classics if you must, but we recommend tearing into the sea salt bourbon caramel and blackberry lavender.

For a city that’s often hamstrung by booze-related blue laws, Boston sure has a fine collection of breweries. The city’s most famous brewer is Samuel Adams, the Revolutionary and “maltster” for whom the local brewing company is named. Tours of the brewery in Jamaica Plain are as affordable (suggested donation $2!) as they are entertaining. But recent years have seen an indie brewery boom across the city. Taste small-batch farmhouse-style ales at Fort Point’s Trillium Brewing Company, or experimental suds at Somerville’s Aeronaut Brewing Company, founded by a science-focused trio with MIT connections. The taproom has a neighborhood block party vibe, often enhanced with live music and food trucks parked outside.

The beloved SoWa Open Market (SoWa stands for “South of Washington,” if you were wondering) runs every Sunday from May through October. The area erupts into a weekly street fest that draws visitors from all over the city and beyond; a farmers' market, craft and antique vendors, and a Food Truck Court are only some of the attractions. And there's more inside the market building—the SoWa Vintage Market offers stall after stall of quirky vintage clothes and housewares.

Compulsive garage sale browsers, jewelry collectors, interior decorators and treasure-hunters of all kinds love the Cambridge Antique Market for its five floors of vintage and antique finds and its T-accessible location. Most of the dealers specialize in specific items and eras, so ask around if you’re looking for something in particular. There's also an entire basement of refurbished vintage bicycles.

After nearly collapsing during the darkest days of the Big Dig, Boston’s historic open-air market has bounced back and then some. It’s thanks to the tenacity of the vendors and customers who continued to show up for the heavily discounted wholesale fruit, vegetables and fresh fish. And, post-Big Dig, the nearby Greenway is at your disposal for a post-shopping stroll. (Dawn–dusk.)

While independent boutiques are becoming an endangered species on Newbury Street (to find those, head to the South End), Boston’s premier retail strip wins hands-down for sheer volume and variety. Between Arlington Street and Massachusetts Avenue, eight blocks of bow-fronted brick townhouses are stuffed with everything from ultra-luxe designers like Chanel and Burberry to chic chain boutiques (Scoop NYC, Intermix, Rag & Bone) and cheap fashion. With galleries, nail bars, cafés, bars and eateries in the mix, you can easily spend an entire day browsing, relaxing and posing here.