Large Pride rainbow flag flying

Things to do in Boston for Pride Day

By <a href="#author-bio">Stuart Bak</a>
By Stuart Bak

Boston’s Pride For The People parade and festival is one of the biggest, brightest and most beautiful in the States, pulling in several thousand participants and around a million spectators for its week-long celebration of love, diversity and inclusion. Baked beans, the Boston Red Sox and that bar ‘where everybody knows your name’ ain't the only thinks to get excited about around these parts: there are also some fine, buzzy ‘gayborhoods’ to explore, like South End, Jones Hill and Jamaica Plain, all of which transform into oceans of rainbow flags and lights for Pride. The week promises all manner of events across the city, from burlesque nights to brewery cookouts, fashion shows and queer cinema. Raise your rainbow flag and dive in for our guide to all the best things to do in Boston on and around Pride Day…

Pride Parade, Block Party & Festival

Boston building lit up in rainbow colors

There will be oodles of fun LGBTQ+ events taking place in Boston through Pride Month, with the majority happening in the days leading up to the parade and festival. We’re talking movie screenings, drag brunches, community events, queer walking tours, picnics, bar crawls and much more. The top of the iconic Prudential Tower will light up in rainbow colors to kick off Pride Month and again on the day of the parade, in support of the LGBTQ+ community. Check local listings for further info and tickets on all June events in Boston.

The big day usually lands on the first or second Saturday of June, when revelers line the streets of the South End to catch a glimpse of outrageous floats, flamboyant drag queens, marching bands, stilt walkers and all manner of other extravagantly garbed participants and performers. The Boston Pride For The People Parade kicks off late morning at Copley Square, painting its celebratory rainbow across the South End before landing up at Boston Common for a top-notch family festival complete with DJs, drag queens and international headline acts. The festival is free and runs from around midday until early evening.

Boston church with rainbow flags

Meanwhile, over at City Plaza, there’s a slightly more grown-up vibe at the free Pride Block Party, which runs for a couple more hours after the Boston Common festival wraps up. This one’s for 21+ attendees only, and promises rather more risqué entertainment in the form of foul-mouthed drag kings and queens, pole dancers and more. New England craft breweries provide the lubrication and DJs spin the party tunes until around 8PM.

Top Tip: Boston Pride for the People recommends Arlington St and Boylston St subway stations on the green line or Back Bay Station on the orange line for the best Parade-viewing opportunities. But get there in plenty of time as it does get extremely busy!

Find about more about the next Boston Pride For The People event here.

Boston Pride After Parties

Club DJ in action

Fear not: the end of ‘official’ festivities does not mean the party’s over. Far from it, in fact. Indeed, Boston’s Pride after parties are the stuff of legend. Hit up South End stalwart Club Café on Columbus Avenue for some of its legendary cabaret and late-night dancing. The fabulous Liberty Hotel – an utterly transformed former prison in Beacon Hill – usually has a number of events running through Pride Month, including brunches, fashion parades and more. That there will be DJs and live acts playing into the small hours on Pride Saturday is a given.

Try the lively Midway Café, a well-established dive bar in Jamaica Plain with regular live music, or mosey over to Dorchester dBar for craft cocktails and all-night dancing at one of Boston’s best-loved LGBTQ+ clubs.

It’s the morning after the night before, so what better than a rejuvenating drag brunch to help brush those cobwebs away? There will be dozens of these running across Boston during Pride Month, with local favorites including South End Mexican restaurant Cósmica, the Boston Summer Shack over in Back Bay, and the aforementioned Liberty Hotel. Bloody Marys and mimosas naturally come as standard. Again, local listings are your friend for the latest info on all Boston club nights and brunches.

LGBTQ+ Culture in Boston

Plaque on the Boston Freedom Trail

Something of a trailblazer, Boston is one of those places that’s very much *steeped* in history. Not only the birthplace of the American Revolution, it’s also the capital of Massachusetts, famously the first US state to legalize gay marriage. Go Boston!

As a result, there’s plenty of queer culture to explore, and this is brought to the fore during Pride Month, where museums, walking tours and even castles get in on the action.

The Freedom Trail comprises 16 historic Boston monuments and locations that, between them, contain the entire history of Beantown. There are walking tours of the route – which includes Boston Common, the 17th-century King’s Chapel cemetery and Paul Revere’s House, year-round, many with guides in period dress. Pride Month sees the addition of an excellent ‘Rainbow Revolutionaries’ option, highlighting key players in Boston’s LGBTQ+ community (and their fight for liberty) through the ages.

Hairy ankles in high heels

For something a little (ok: a lot) more light-hearted, pop on your heels and hop aboard a drag-tacular trolley tour of Boston’s most significant female and queer landmarks. However, we’d recommend flat shoes for top Boston LGBTQ+ walking tours like this one.

It’s also worth a day trip out to Hammond Castle and museum up the coast in Gloucester. Founder John Hammond is something of an LGBTQ+ Massachusetts icon so it’s no surprise that there are several special events running here throughout Pride Month, including exhibitions, readings and film screenings.

Visit Boston’s Top Attractions

Boston's famous swan boats

If you’re in town for a few days and fancy fitting some serious Beantown sightseeing around all that drinking, dancing and drag-brunching, the Go Boston pass is your friend. Choose an Explorer or All-Inclusive option, depending on whether you have specific attractions in your sights or simply want the freedom to visit as many as you’d like over several days. The pass can save you up to 50% on standard entry prices for Boston tours, activities and attractions and includes:

  • The View Boston Observation Deck, up top of the iconic Prudential Tower.
  • A tour of Fenway Park Stadium, home of the legendary Boston Red Sox.
  • A ride on the famous Boston swan boats.
  • The absolute treasure trove of art and artifacts that is the Boston Museum of Fine Arts.
  • A sunset cruise of the Charles River Basin.
  • A guided tour of the charming clapboard farmhouse in nearby Concord, where Louisa May Alcott wrote (and set) American literary masterpiece ‘Little Women’.
  • ...and much more!

Find out more and choose your Boston attractions pass here.

Pride parade participants draped in rainbow flags
Stuart Bak
Stuart Bak
Freelance travel writer

Stu caught the travel bug at an early age, thanks to childhood road trips to the south of France squeezed into the back of a Ford Cortina with two brothers and a Sony Walkman. Now a freelance writer living on the Norfolk coast, Stu has produced content for travel giants including Frommer’s, British Airways, Expedia, Mr & Mrs Smith, and now Go City. His most memorable travel experiences include drinking kava with the locals in Fiji and pranging a taxi driver’s car in the Honduran capital.

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Sunrise over the George Washington statue in Boston's Public Garden
Blog

Things to do in Boston in the Morning

Beautiful Boston is at its most breathtaking in the morning, as fishing boats bob along the Charles River and the city’s parks and gardens are at their most restful. It’s also a fine time to check out Beantown’s most popular attractions – including the Freedom Trail and Paul Revere House – before the crowds arrive. Read on for our guide to all the best things to do in Boston in the morning...
Stuart Bak
Stuart Bak
north end boston
Blog

Things to do in North End, Boston

Heading to Boston for your vacation, and keeping an eye on North End? Good choice! North End has a load of great things to do and places to eat and drink. We're going to talk about those now. Scroll down, and discover our picks for the best things to do in North End, Boston! Including: Paul Revere House Old North Church Improv Asylum Great food Great nights out and more! A House Revered Let's start our trip through North End with some history. Boston was the heart of the revolutionary efforts when the US fought for independence. On one fateful night in 1775, one man saw a frightening sight. Men clad in red, as far as the eye could see. Invaders, coming to claim what they thought was theirs. But this bastion of chivalry wasn't having any of that. So he valiantly mounted his faithful steed, and he rode. God, did he ride. If he didn't, the war could be lost. He rode and rode until he reached his countrymen. And when he pulled up in front of them, he uttered four words immortalized in this nation's heart forevermore. "The British are coming." Or did he? Find out at the Paul Revere House! Not only will you learn more about the legend himself, but you'll also discover whether there's any truth to the poem that utters his famous phrase. One of the oldest buildings in Boston, step inside the house and get a fascinating insight into colonial history. Tour the historic rooms and see authentic period furniture, real documents, and silver made by Paul himself. Clearly, he was a man of many talents. Not immortal, though, so there is that. A Statue Revered And if all that wasn't enough Revere for you, go and see the massive statue of him for yourself! Sculptor Cyrus Dallin designed this bronze statue of Revere riding his horse. His hand raised, we can only assume what Paul was gesticulating towards. Was it his fellow countrymen, patriots one and all? Or was he shooing a dog out of his path? We will never, ever know. Old North Church Sticking with the historical theme, let's talk churches. Whether you're a believer or not, there's no denying the beauty that went into their creation and ornamentation. Why not go and see one of the nation's longest-standing churches, Old North Church? Built back in 1723, and inspired by the works of British male Sir Christopher Wren, it played a key part in the War of Independence. The church's steeple held lanterns that warned the minutemen of incoming British forces. See, learning can be fun! These days, it may be less exciting, but it's still just as beautiful! You can enjoy a self-guided tour of the sanctuary, a fun family scavenger hunt, and even tour the crypt and the gallery. Of all the things to do in North End, Boston, this is definitely one of them. A gift for you In the market for some keepsakes, or perhaps a gift or two for the people you left behind? Check out the Boston Gift Shop! It's right by Paul Revere's House, so if you've been following our instructions, you'll be thereabouts anyway. For over 100 years, they've been offering reasonably priced and decently made Independence memorabilia to visitors from far and wide. So go pick up some swag and either give it away, or rub it in people's faces. It's really up to you! Winging it crazy Out with the old, in with the new, as we continue with our tour of Boston's North End. Looking for things to do? How about laughing until you can't stop? Until it hurts? If that sounds delightful, give Improv Asylum a browse. For over 20 years, they've hosted improv and sketch comedy shows for literally anyone willing to pay money. They aim to put one on every night, but head there on the weekend, and you might be spoiled by two or more! While they tend to be for all ages, midnight shows often take a turn into the crass and adult. Just what us adults want! And if that wasn't enough (is it ever?), you can also attend workshops and learn how to actually be funny. That would be nice, wouldn't it? Food, glorious food Food, yeah? It's pretty good. A necessity for humans, food is the fuel that keeps us going. Some people think they can survive on sunlight and water, but they're wrong. That's plants, not people. And when that fuel inevitably runs out, you'll be needing a top-up. Thankfully, Boston's North End has some great places to eat some great food. There are our favorites. Spoiler alert - they're all Italian. For nearly a century, Regina Pizzeria has been providing hungry visitors with fantastic pizza. And once they eat it, they're no longer hungry. Brilliant! They attest to being Boston's original Pizzeria, and who are you to question that? You weren't around then. With a menu full of the usual greats, cooked with comfort and care from scratch, it's a must-visit for slice aficionados. Fancy throwing some seafood into the mix? Check out The Daily Catch, because their Sicilian seafood pasta fishes will blow your mind and fill your tummy. Born from the mind of Paul Freddura, who turned his knowledge of the seafood trade into seafood plates, it's easily one of the best restaurants in North End. Or, if you want something a little out of the way, check out Maria's Pastry Shop. Inside, you'll find delightful Italian pastries both sweet and savory, and the best cannoli money can buy. Drink it up Let's round off this list with a round of our own. Looking for a place to sit and drink till the early morn? Here are our picks. Ex speakeasy Stanza dei Sigari is now a cigar parlor and liquor lounge. Stepping inside is like being transported back to the roaring '20s. With an enviable cocktail menu and a host of fine liquors to sample, it's a great place to wet your whistle. Looking for something a little more gutter-like? Try Corner Cafe, a dive bar with plenty of beers, sports on the TV, and a handful of cocktails classics like margaritas. It's cash only, so bear that in mind. And that's our list of the best things to do in North End, Boston!
Dom Bewley
downtown boston
Blog

Things to do in Downtown, Boston

Downtown. Things will be great when you're Downtown. No song has ever been truer than Petula Clark's classic. Boston's Downtown area is one of the city's best, with plenty to do, see, and experience. It's dripping with history that dates all the way back to the War of Independence, so why not go and discover its greatness for yourself? There's no need to take our word for it; we'll show you why. Right now. Read on, and discover the wonders of Boston's Downtown district. Here are our recommendations for the best things to do on your vacation! Including: New England Aquarium Chinatown Freedom Trail Fenway Park Museum of Fine Arts See life Let's start our tour of Downtown under the sea. See sea life like never before at the New England Aquarium! Perfect for kids and big kids alike, this fantastic aquarium is one of Boston's crown jewels. Go nose-to-nose with seals, waddle to the penguin enclosure, be mesmerized by the giant Pacific octopus, and much more! There are a number of exhibits worth checking out at the moment, such as the Amazon Rainforest, where you'll discover piranhas, anacondas, and poison dart frogs! Or, stop by the Indo-Pacific Coral Reef. Here, you'll go on a journey through the waters of the Pacific, seeing coral catsharks, unicorn tangs, blue-striped cleaner fish, and all the beauty these natural habitats exude! Easily one of the best things to do in Downtown, this is one Boston attraction that you cannot pass up on! Eastern Promise Switching gears to something on dry land. Boston is one of many American cities that is fortunate enough to have its own Chinatown - the third biggest of its kind in the country! For those that don't know, the US we know and love today wouldn't have been possible without Chinese immigrants. So go give them some love, and indulge in some of the finer things while you're at it. Step over the threshold of the remarkable Chinatown Gate, and you'll be transported to a world of great food, great people, and plenty of knickknacks, clothes, and jewelry to purchase. And if your vacation happens to land on Chinese New Year, you're in for a sumptuous treat of performance, lights, and fireworks! Freedom is free Want to explore the nation's history, and walk in our forefathers' footsteps along many historical monuments to American Independence? Then take a historical tour of the Freedom Trail. Beside your fancy guide, replete with authentic accent, language, and costume, you'll explore Boston's famous red brick path and learn about over 250 years of American history. You'll see many historic sites, including Boston Common, Massachusetts State House, Park Street Church, the Boston Massacre Site, and King's Chapel. And, you'll hear from patriots like Josiah Quincy and Phillis Wheatley as they tell you their own stories and share lively anecdotes about the places, events, and drama of the American Revolution and beyond. Easily one of the best things to do in Downtown if you're taking a vacation in Boston. If you miss out, maybe you're a red coat after all. Homerun fun Are you a sports person? Does the thought of people getting together and competing against one another excite you? Do you like balls? Well then, you must be a fan of the old baseball. Right? Boston is home to one of the most recognizable teams on the planet, the Boston Red Sox. Their socks? Red. Their arena? Fenway Park. So why not take a tour of this historic stadium and learn more about the stadium's history, the players that stepped into the diamond, and the team's highs and lows throughout the years. For a whole hour, you'll go behind the scenes at Fenway Park, exploring the ground, it's history, and the story of arguably the greatest baller of all time, Babe Routh, who called Fenway Park home. Keep your eyes peeled for Pesky's Pole, named after contact hitter Johnny Pesky, and the Red Seat, where the longest home run ever hit landed at Fenway Park. Given it's the longest-running ballpark on the planet, you best go while the getting's good! Get arty Boston is one of the country's oldest cities, with its own rich history and culture. But it's not the only culture you'll find there. In fact, one of the biggest Art Museums on the planet calls the city home. We're talking, of course, about the Museum of Fine Arts, Boston. Inside, you'll find over half a million works of art. Yes, really. 500,000 art pieces lie within its myriad galleries and buildings. Spanning millennia, you'll find works from ancient civilizations as well as more modern marvels from the likes of Monet and van Gogh. One unmissable exhibit currently showing is The Art of the Americas. Spanning two continents and encompassing 3000 years of culture, it takes a deep dive into works from ancient American civilizations like the Mesoamericans, all the way to prominent New York artists. The exhibit is a work of art itself, taking years to compile and curate. It really has to be seen to be believed, and is easily one of the best things to do in Boston's Downtown. But after all that wandering and wondering, you might be feeling famished. Never mind that, because the museum's got some great onsite solutions to your hunger problems! If the weather outside's fine, head to the Calderwood Courtyard and sample the delights at The Garden Cafeteria, where you can pick up small bites like pizza slices, subs, burgers, and even desserts. Or, if something small won't cut it, then the New American Cafe will sort you out. Their curated menu of filling dishes will hit the spot. And that's our list of the best things to do in Downtown, Boston! Looking for anything else Boston-related? If you're visiting from out of state or across the sea, check out our picks for the best places to stay. Looking for more of Boston's amazing culture? Check out our museum guide. Just want to learn more about the city? Check out some fun facts!
Dom Bewley

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