The 17 All-Time Greatest Things to Do in Boston

Rock out at the OG House of Blues, chug beers at dives, and learn about the city's infamous art heist.

Things to Do in Boston This Fall and Winter
George Washington Equestrian Statue at Public Garden | Getty Images, photo illustration by Thrillist
George Washington Equestrian Statue at Public Garden | Getty Images, photo illustration by Thrillist
All Time Greats is the ultimate city bucket list. Whether you’re a local or a visitor, consider this the essential guide to getting the most out of Boston. Looking for events happening this weekend? Check out our Boston weekend guide.

Boston is old AF, and it's the magic fairy dust that makes many of its experiences so unique. The city's seamless amalgam of old and new is everywhere, which means you don't need to go out of your way to explore its history—it's just peppered in wherever you go.

Even those who don't fancy themselves a history buff will have delightfully nerdish ah-ha moments, like when eating a nice dinner in a perfectly preserved jail cell from the 1800s. Sure, there’s plenty of recreational weed dispensaries and nearby stargazing, but don't miss out on the city's immersive experiences. You can take a riverboat tour of the architecture, rock out at the OG House of Blues, chug cheap beer at a dive bar, or try to solve the city's famous art heist.

Things to Do in Boston in Fall and Winter 

Ice Skating at Boston Common Frog Pond

Starting in November, The Boston Common Frog Pond transforms into a winter wonderland. While the warmer days here are usually relegated to the carousel, and spray pool, winter is wholeheartedly dedicated to the magic of ice skating. The surrounding trees twinkle with lights, and it's a rom-com-like scene of people laughing and trying to stay upright. You can rent skates; just remember your woolen socks. When you're done, head to Emmets Irish Pub & Restaurant and warm up with some whiskey and traditional Irish beef stew.

Things to Do in Boston This Fall and Winter
Fenway Park | Photo by Matt Stone/MediaNews Group/Boston Herald via Getty Images

Enjoy the Outdoors in Boston 

Fenway Park

The oldest baseball park in Major League Baseball still has plenty of tricks up her sleeve. Red Sox Nation members can arrive early to watch batting practice during the regular season, but anyone can get in on a Fenway Park Tour, including the popular Fenway in Fifteen for a quick 15-minute peek. You can also take to the skies in a Boston Helicopter Tour for a bird's eye view of the historic park. Afterwards, edit those selfies with drinks at The Bleacher Bar, which is built directly into the wall adjoining the park.

Boating on the Charles River

Not only is Boston a harbor city, but it's been doubly gifted with The Charles River. Some of our most beloved activities include the annual (and oh-so-elite) Head of The Charles Regatta and the slightly less competitive iconic Swan Boats in the Boston Public Garden. The whimsical swans have some lighthearted competition, however, from the famous Boston Duck Tours. Commonly referred to as Duck Boats, the '40s replica amphibious vehicles travel by land and river, showing people the city's famous landmarks. The Charles Riverboat Company puts a unique twist on things with its Boston architecture riverboat cruise. Or, stay on dry land and visit the Boston Tea Party Ships & Museum.

The Running Scene

Boston boasts a lot of "firsts," the most famous of which is probably The Boston Marathon, the world's oldest annual marathon. Some folks drive the 26.2-mile course for fun, but you can skip to the good stuff—the finish line across from the Boston Public Library and Old South Church in Boston's Copley Square—both worthwhile local bucket-list sights. If running isn't your go-to sport, but you still want to dabble in Boston's legendary haunts, hop in on a game of basketball or pickleball at the TRACK at new balance. Not only will you get a deal at just $10, but you can also get a glimpse of the new-to-Boston track, designed to be the fastest in the world.

Things to Do in Boston This Fall and Winter
Paradise Rock Club | Photo courtesy of Paradise Rock Club

See Live Music in Boston

Citizens House of Blues

Talk about phenomenal music mojo; House of Blues (now Citizens House of Blues)—recognized worldwide as a music mecca—started here in Boston. Of course, the site has changed to Fenway, but it's still home to the soulful stank of live performance and the emotional exfoliation that only music can inspire. Obviously, blues is on the set list, but the venue features artists of all genres, from pop and hip-hop to country and gospel.

Boston Symphony Orchestra

The first concert of the Boston Symphony Orchestra was in 1881, but the organization has successfully navigated the ever-changing cultural landscape. For example, the annual holiday show is an absolute joy-fest; the Holiday Pops musicians play classic holiday jams, and there's even a sing-along at the end. That aside, you can often find tribute nights with over-the-top orchestral renditions dedicated to composers, like the person behind film soundtracks such as Star Wars, Jaws, and Jurassic Park. Plus, the BSO sometimes offers Casual Friday performances, tickets to rehearsals, and sensory-friendly editions of popular concerts.

Classic Music Venues

When it comes to standout music venues, the Paradise Rock Club has hosted some of our all-time greats like Tom Petty, Rage Against the Machine, and Billie Eilish. Brimming with cozy, subterranean vibes, the all-genres Lizard Lounge in Cambridge is especially popular for a stellar Sunday night Poetry Jam & Slam. Though it’s impossible to include all the music houses, The Sinclair in Cambridge and Brighton Music Hall in Allston are also legendary.

New Music Venues 

A few of Boston's essential music spots are shaking things up a bit. The Porch—a Southern Fare & Juke Joint—is a little slice of Southern goodness with authentic barbecue and live country, blues, and alt-country music. Whiskey is a popular sip there, but the focus is more vine-based at City Winery—an elegant riff on the sticky floors of some bass-booming music venues. Taking the tunes outdoors, shout-out to the ever-welcoming Hatch Shell, the warm weather darling of the Charles River Esplanade in the Back Bay, which is known for outdoor movies in the area and free open-air performances by Landmarks Orchestra and other awesomeness.

Things to Do in Boston This Fall and Winter
An empty frame with the wallpaper showing through, where Rembrandt's "The Storm on the Sea of Galilee," circa 1633, once was. | Photo by David L Ryan/The Boston Globe via Getty Images

Where to See Arts and Culture in Boston

Isabella Stewart Gardner Museum

Isabella Stewart Gardner Museum’s courtyard will make you gasp and clutch your pearls. It gives major Gilded Age vibes, and the museum itself has an extraordinary collection and continues prioritizing music, art, and horticulture just as its founder, Isabella Stewart Gardner, intended. When it was famously robbed in 1990—a crime still unsolved—the institution purposely left the empty frames on the wall. Visitors can delve into the mystery, attend many concerts, or sit quietly in the courtyard drawing, journaling, or conspiring to find the missing art.

Brattle Book Shop

Can bibliophiles and Bruins fanatics live harmoniously? We say yes, and, in fact, they're often one and the same here in Boston—home to the famed Brattle Book Shop. Far from a typical used bookstore, Brattle is stocked with two floors dedicated to used books, a third solely for rare and antiquarian tomes, and a discounted book area. They've got over 250,000 books, prints, postcards and ephemera, and (squeal!) maps. Hardly a pop-in-and-be-on-your-way shop, Brattle is a place to wile away the afternoon. Alternatively, you can fill out this handy form, and they'll help you find the book of your dreams.

Boston's Evolving Architecture

Adaptive reuse is a fancy term for keeping historic buildings preserved while incorporating them into modern-day use. For example, The Liberty Hotel, originally an 1851 jail, still has many original elements and is home to restaurants like CLINK, inside a preserved jail cell.

You can also apply the concept to the Seaport District, and see the area's transformation by binge-watching the '80s series about a private investigator who loves lunch at The Ritz-Carlton, Spenser: For Hire. Spenser regularly tackled (alleged) lawbreakers and organized crime in locales where we now meander Boston Harbor Walk, eat lobsters at Legal Sea Foods Harborside, and peruse art at The Institute of Contemporary Art. Spenser would never believe we casually toss darts at Flight Club—for fun and not to thwart would-be bad guys.

Things to Do in Boston This Fall and Winter
Dorchester Brewing Co. | Photo courtesy of Dorchester Brewing Co.

Where to Drink in Boston

Boston Speakeasies

If you want a snapshot of a city's culture, wander its speakeasies. Boston's best-known speakeasy, Bodega, is a nondescript convenience store. Once inside, a vending machine gives way to a secret, high-end sneaker and fashion hub. Similarly, the Seaport's Borrachito Taqueria & Spirits looks like a simple taco takeout joint—until you ask them to open the enormous freezer door, behind which you'll find an entire cool AF bar.

Downtown, you can only access Yvonne's unapologetic glamour through a door at the back of a blow-dry bar. They're big on high-end spirits and discretion–in that champagne-fueled shenanigans sort of way.

Boston's Breweries

On the one hand, we utterly adore Sam Adams Brewery. They're steeped in Boston culture, host kickass events, and offer tours of the Jamaica Plain brewery. Selfishly, we're giddy AF knowing how spoiled we are with Trillium Brewing CompanyWinter Hill Brewing, and Dorchester Brewing Co. at our feet as well. It also makes us pretty hoppy that employee-owned Harpoon Brewery and Democracy Brewing got together to create a collaboration beer that stands as a celebration of their Boston staff. Harpoon offers a dizzying array of fun events, and we say hell ya to Democracy's Friday night piano bar sing-alongs and Saturday night comedy shows.

The Tall Ship

East Boston
Instant classics are tough to come by and nearly impossible in the local bar scene—until Tall Ship Boston came along. Moored on Pier One in East Boston, the ship is a commanding 245 feet long—with mahogany bars and an endless supply of fresh oysters and cocktails. Prone to seasickness? No worries. Enjoy the refined yacht vibes and order another Knotty Nauti tequila drink because this boat ain't moving. In fact, alongside the ship, there's a 40,000-square-foot waterfront oasis with gorgeous lounge seating, yard games, live entertainment, and food trucks. The Tall Ship is seasonal and usually opens in May and closes whenever management finally yields to New England's finicky cold-weather season.

Bully Boy Distillers

The Prohibition era pretty much sucked, other than the snappy outfits, of course. Alcohol was an outlaw, and Boston—along with everyone else—had to shutter its distilleries. For those keeping track, Prohibition ended in 1933, and somehow, Boston went sans distilleries until Bully Boy Distillers came along in 2010. We're all mighty grateful for the Willis brothers and their damn fine spirits, including a nod to Boston's rum roots. Luckily, they've got a gorgeous bar and tasting room in Roxbury's burgeoning Newmarket District.

Bell in Hand Tavern

Government Center
Though that pesky Prohibition thing temporarily closed it down, Bell in Hand Tavern is otherwise the oldest continuously operating bar in the country. The name is a little wink to the owner's job as the town crier, and honestly, we love that Bostonians have been rockin' a side hustle since days of yore. Ever since the first pour in 1795, the bar's been known as a chill, welcoming spot. As it turns out, this block must have been the hot spot for food and bevy innovation back in the day because Union Oyster House—America's oldest restaurant, established in 1826—is a few doors down.

Boston Dive Bars

The iconic bar, The Tam, has long claimed the title of best dive bar, but if a dive bar says it's a dive bar… is it really a dive? It's small, crowded, cash-only, and the walls are plastered with eons of memorabilia. In short, it's freaking awesome. Along those lines, The Sil (aka Silhouette Lounge) in Allston has cheap pitchers, live music, and pinball, and if you get a Sil tattoo, they'll give you one free Sil-style hot dog every day for life. You're on your own with the indigestion, but you'll be an absolute legend. And for the dive bar purists among us, we purport that the diviest of all dive bars wouldn't have a website. So, if you're looking for a no-frills, cheap booze hang, Eastie's iconic Eddie C's is your spot.

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Melanie Carden is a private chef turned travel writer. She’s equal parts adrenaline-seeker and Golden Girls vibes. You can find her trying new things, thrifting for treasures, grinding it out on a trail, or lounging on a picnic blanket—Aperol spritz in hand. She's fickle about social, but the sporadic nuggets are worth the wait—cricket tacos, anyone?