10+ Things to Do in Boston Labor Day 2019 Weekend & September

By Katie Sagal
Published: July 18, 2024

The end of summer, traditionally marked by Labor Day, is a great time to enjoy that last getaway before school and work pick back up again. If you're taking a Labor Day weekend trip to Boston, you won't be short of things to do. Many fun local activities and attractions in Boston offer special events or exhibits at the end of August into September, so there's a lot of promise in late summer vacations. So make the most of the last few days of summer in Boston! If you’re looking for things to do in Boston Labor Day weekend 2019 and into September, check out our list of the best local activities and attractions. A few ideas include:

  • St. Anthony's Feast
  • New England Aquarium Whale Watch
  • Fenway Park Tour
  • Swan Boats of Boston
  • Somerville Fluff Festival
  • And more!

Save on Attraction Admission

Regular admission to a number of these Boston attractions are included on the Go Boston® pass. Choose as you go from dozens of top attractions and save up to 55% on combined admission vs paying at the gate. See all available passes, attractions & prices – Learn more. Please note, the special events taking place at these attractions may be separately ticketed and not included on the Go Boston pass. Searching for more events later in the fall? Check out our Boston Fall Events post for fun activities in October and November.

St. Anthony’s Feast

August 22-25, 2019 The North End

Headlining the weekend before Labor Day is the very Boston-esque St. Anthony’s Feast. This has long been famous as the largest Italian religious festival in New England. It’s a huge affair that takes over much of the North End neighborhood: part parade, part pageantry, part ceremony, and all excitement. The actual procession begins at noon on Sunday. The Santa Lucia festival brings up the rear on Monday, a shorter but no less grand celebration. This is a must do for a local Labor Day experience -- be sure to add it to your itinerary. For a full schedule of events, consult the St. Anthony’s Feast website Getting In: Admission to St. Anthony's Feast is free.

New England Aquarium Whale Watch

humpback-whale-feeding-during-watch

There are few things that animal lovers appreciate more than a chance to see amazing animals in person. Boston Harbor Cruises offers a popular whale-watching cruise that departs from the pier adjacent to the New England Aquarium (a very convenient place to board). Head out to Stellwagen Bank Marine Sanctuary for a truly inspiring encounter with some of the ocean’s most majestic inhabitants. Whether you're a true fan of the sea or just love the wonder of seeing such giant creatures relatively close, you’ll have an ocean experience you'll never forget. Keep in mind that the scheduled tours will become less frequent once you pass Labor Day, but the cruise will still run in good weather. Getting In: New England Aquarium Whale Watch tickets are included as an option on 3, 5, and 7-Day Go Boston pass.

Fenway Park Tour

fenway-park-boston

This Labor Day weekend, the Red Sox will be playing the Los Angeles Angels on September 1. Catching a baseball game at the Red Sox home stadium would be a great way to celebrate the Labor Day weekend. But if you don't manage to get tickets, baseball fans will love the chance to tour the stadium. Explore the many iconic sites of baseball's most historic stadium, from the lone red seat to Pesky's Pole to the Green Monster. It's a great chance to go behind the scenes at this very special venue. Getting In: Fenway Park Tour tickets are included with the Go Boston pass.

Hop-on Hop-off Bus Tour

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If you're new to Boston this Labor Day weekend, then one smart attraction choice for you is a comprehensive bus tour of the city. Hop-on hop-off options give you the flexibility to see what you want, when you want, and skip what you aren't interested in. See the sights of Boston from the bus and explore the areas you really want to see. Plus, the ticket's good for two days, giving you extra freedom on your adventures. Getting In: Hop On Hop Off Boston Trolley Tour tickets are included with the Go Boston pass.

Go for a Bike Ride

tourist-ride-bike-around-boston-university

Bike rides are a win-win in our book. The kids get to have fun being active and enjoying the outdoors, and they’re simultaneously getting some exercise and burning off all that excess energy. Pedal through Boston Common and the Boston Public Gardens, and then down to the Harborwalk bike trail. You can also choose to ride along the Charles River, which offers miles of trails on either side. This late in the summer, you'll be contending with other cyclists, runners, and those just enjoying a stroll. Bike riding is a great way to see Boston while spending some time outdoors and enjoying the weather. Getting In: Boston Bike Rentals by Urban AdvenTours are included on the Go Boston pass.

Swan Boats of Boston

colorful-spring-scene-trees-blossoming-swan

The Swan Boats in the Boston Public Gardens are an iconic summertime attraction. Take a nice, relaxing ride to slow down your Labor Day weekend and take in the town. It's a fun activity for kids, or for couples, and is a great way to evoke the true spirit of summer in Boston. The Swan Boats are the perfect warm weather activity to say goodbye to summer. Getting In: Boston Swan Boat Rides are included on the Go Boston pass.

The Boston Children’s Museum

While there are tons of great museums in the Boston area that appeal to the whole family, the Boston Children’s Museum is truly the perfect candidate for keeping the kids happy. You’ll find tons of interactive exhibits that focus on everything from science and environmental awareness to culture and the arts. The kids will enjoy playing while the learn - it's the best of both! Be sure to check their events calendar for any special exhibits or attractions that may occur during your visit. Getting In: Boston Children's Museum tickets are included on the Go Boston pass.

All Hands to Mischief! at the USS Constitution Museum

August 31 - September 3, 2019 Charlestown Navy Yard

Come to the USS Constitution Museum this Labor Day weekend to learn about how sailors spent their spare time at sea. The hands-on, interactive activities are great for kids. You can practice writing with a quill pen, play your hand at a nineteenth century board game, and get a temporary nautical tattoo. If you're interested in Old Ironsides herself, consider a cruise like the USS Constitution Cruise which escorts you out to the ship in Boston's Inner Harbor and past other major sights like the Bunker Hill Monument and the Boston Tea Party boat. Getting In: Admission to the USS Constitution Museum is separately ticketed and is not included with the Go Boston pass. For more information about this attraction and to purchase tickets, visit the attraction website. USS Constitution Cruise tickets are included with the Go Boston pass.

The Boston Arts Festival

September 8 & 9, 2019, 11:00 am - 6:30 pm Christopher Columbus Park

gardens-christopher-columbus-waterfront-park-north

Enjoy musical performances, clever crafts, and inspiring art created by the Boston area’s top artists and artisans as you roam the beautiful waterfront Christopher Columbus Park. You’ll find everything from photography and painting to glasswork and jewelry. Bonus: there are plenty of items for sale in addition to those items only for exhibition purposes. The whole family will enjoy the plethora of fun activities and performance options designed to appeal to both kids and adults (thankfully). You’ll leave feeling like an expert in Boston’s “ahts scene.” Getting In: Admission to the Boston Arts Festival is free.

“Summer in the City” Movie Series

Tuesday – Friday, all summer Boston Harbor Hotel

boston-harbour-skyline-night

Each summer the Boston Harbor Hotel hosts a family movie and music series. Tuesdays, Wednesdays, and Thursdays are devoted to musical performances by a wide variety of bands (categories are “Summer Soul,” “Rat Pack,” and “Blues Barge”), providing an incredibly atmospheric dining experience to dine the hotel restaurant. Every Friday they show a movie by moonlight. The Boston Harbor Hotel is conveniently located off the scenic Fort Point Channel and the pedestrian favorite Harborwalk – the ideal route for a waterfront stroll in Boston. Getting In: Admission to the "Summer in the City" series is free.

What the Fluff?

September 21, 2019 Union Square, Somerville

This delightful event is perfect for visitors of all ages. Now in its 13th year, this fun festival celebrates all things fluff -- the delectable marshmallow treat that was invented right in Somerville back in 1917. The festival incorporates live music, toys and games for kids, beverages for adults, and tons of fluff-related food items. There's even a cooking contest for the best inventive fluff recipe. Deadline for submissions is September 18! Somerville is located just a little bit north west of Boston proper -- you can get to Union Square easily via bus. Getting In: Admission to the Fluff Festival is free.

Remember to Save on Attraction Admission

So there are a few examples of fun and exciting things to do in Boston during Labor Day Weekend and into September. There is so much to do in Boston that you're sure to have a great end to your summer vacation. Remember, some of these great attraction options are included on the Go Boston pass, where you can save up to 55% on combined admission vs paying at the gate. Please note, the Labor Day weekend events taking place at some of these attractions may be separately ticketed and not included with the Go Boston pass. We hope you consider visiting some of these attractions to help round out your summer vacation in Boston in style.

Katie Sagal
Go City Travel Expert

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Boston skyline at night
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New Year's Eve in Boston - Things to do

Rich history and a fine party scene means there’s plenty to keep you occupied in Boston on New Year’s Eve. From heritage trails to winter wonderlands, magnificent museums to the city’s beloved sport team stadiums, Boston has it all. New Year is a great time to visit, with plenty going on to keep kids and grown-ups entertained all day long, not to mention the buzzy bar scene and epic firework displays that define this great city’s end-of-year celebrations. Read on for our guide to New Year’s Eve in Boston and the best things to do while you’re in town! Morning: Boston Highlights Crisp winter mornings are made for sightseeing and, as you happen to be in Boston for New Year, well, why the heck not? There’s a glut of activities here – from the historical to the futuristic – that will take up just one or two hours of your New Year’s Eve in Boston. And boy, are some of Beantown’s attractions worth checking out. Take a whistle stop guided tour of the Freedom Trail led by actors in period costume for a deep dive into Boston’s most historic sites, including the golden-domed Massachusetts State House, the site of the Boston Massacre, 17th-century King’s Chapel cemetery and Boston Common, the oldest public park in the United States. Boston’s Museum of Fine Arts is where it's at for culture vultures. Here’s where you can explore 100 galleries of eye-popping art from across the centuries, including ancient Egyptian sculptures, early musical instruments and paintings by the likes of Monet, Van Gogh, Renoir and Kahlo. Don’t miss John Singleton Copley’s portrait of local hero Paul Revere, and the elaborate mural by John Singer Sargent that adorns the rotunda ceiling. Alternatively, get your sports fix on a guided tour of the Sports Museum at the TD Garden arena, legendary home of the Boston Celtics and Boston Bruins; say hey to the seals, snakes, sea turtles and funky rockhopper penguins at the New England Aquarium; or nip just out of town to unleash your inner Jo, Meg, Amy or Beth at the 17th-century former home of Louisa May Alcott, where her novel Little Women was set. Sticking around beyond New Year? Consider an attraction pass from Go City to save $$$ on things to do in Boston, including top attractions, tours, activities and more. Afternoon: Seasonal Events in Boston If you’re looking for things to do in Boston on New Year’s Eve, rejoice! Many of Beantown’s Christmas fairs and festivals continue through New Year and there are even a few brand-new dedicated NYE events to check out. Better yet, many of the afternoon and early evening activities are family friendly, meaning kids can join in the fun too. Zoolights at the Stone Zoo is a magical festive extravaganza, where tree-lined walkways are festooned with thousands of twinkling lights and Yukon Creek – home to black bears, bald eagles, arctic foxes, Canada lynx, reindeer and more – has been given a fairytale festive makeover. Sponsored (perhaps unsurprisingly) by the National Grid, this electrifying experience is sure to give kids (and adults) of all ages a real buzz. Mosey on down to Boston’s Waterfront winter wonderland, where dozens of frozen masterpieces line the Ice Sculpture Stroll, spanning North End, Downtown Waterfront, Charlestown End, and South Boston Waterfront. Follow the trail to the Seaport neighborhood to find a veritable fiesta of fun at Snowport. There are soaring, twinking Christmas trees, an iceless curling rink, après ski lodges, fire pits, a beer tent, street-food stalls, local crafts and more. Eyes peeled for the Snowport mascot, a huge fluffy pink yeti that’s your kids with love. Or be absolutely terrified by, depending on their disposition. As the light begins to fade, make for Copley Square, where the annual First Night Boston Celebrations includes eminently danceable holiday-themed tunes and illuminated ice sculptures. Once you’ve shimmied yourself warm, join the procession to Boston Common for the spectacular early evening firework displays, which kick off around 7PM. Evening: The Best of Boston’s Party Scene The fireworks at Boston Common are repeated periodically throughout the evening, right up to the main event at midnight, but there are plenty more ways to spend  the final hours of New Year’s Eve in Boston. Party your little heart out at suave Rochambeau in the Hynes Convention Center. This one is strictly for over-21s only. And rightly so. After all, sophisticated hors d'oeuvres, speciality seasonal cocktails and dessert bars that groan with sweet treats galore are wasted on the young. There’s a live DJ spinning floorfillers throughout the evening, and a glass of fizz to toast the New Year at midnight. You’ll want to book tickets in advance for this popular annual party. Wrap up extra warm for Boston’s legendary Bow Market Ball Drop. This one is held partly indoors and – shiver – partly al fresco, although patio heaters should help to stave off the worst of the winter chill. A bit of fancy footwork to the live tunes being played by the DJ should also help stop hypothermia setting in. Again, book well in advance if you want to join the party. The price of admission includes a couple of free drinks, some nibbles and other surprises throughout the evening, ahead of the hotly (or should that be coldly) anticipated ball drop at midnight. If it’s heart-swelling romantic firework views that top your New Year’s Eve wish list, the Boston Harbor show is unlikely to disappoint. Get yourself over to Christopher Columbus Park for this awesome midnight extravaganza of colorful pyrotechnics and booming, spirit-lifting music. Entry to the park is free. It commands some of the best views in town, so we’d recommend getting there early to ensure your Boston New Year’s Eve goes off with a bang! Save on activities and attractions in Boston Save on admission to Boston attractions with Go City. Check out @GoCity on Instagram for the latest top tips and attraction info.
Stuart Bak
Stuart Bak
boston souvenirs
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Best Boston Souvenirs

Hello there! Welcome to the gift shop. Sadly, we only have one thing in stock. It's this guide to the best souvenirs in Boston. Hopefully, you aren't looking for ice cream. We don't sell those. But, if you're interested in the best Boston souvenirs, you're in luck, partner. Here's a menu with all of the best souvenirs in Boston. Including: Freedom Trail memorabilia Boston Red Sox souvenirs Harvard attire Baked beans - really Irish things and more! Freedom Trail frills The Freedom Trail is one of Boston's most important historical landmarks. So, why not commemorate your journey down the red brick road with some keepsakes? Right next to the Paul Revere House, you'll find North End Gift Shoppe, which sells all manner of freedom-esque attire, from freedom hats to freedom slacks. Want a freedom snowglobe? No? Well tough luck, because you're buying one before you leave! Why not take a tour that will lead you right there? Godly bothers Ever wondered if a church would dare sell gift shop oddities? Wonder no more; just hop on down to Old North Church and browse through the shop's many Boston-themed souvenirs. Books? Yes. Clothing? Yes. Jewelry? Yes! You can even pick up inspirational items like nativity figures for your very own Jesus Christ-approved Christmas setup. Holy Moses! You're a consumer, Harry! Any Potterphiles out there can also pick up some awesome wizarding merch at the Harry Potter Shop. Grab your wand and fly to Newbury Street, and enter a world of wizarding wonder. Mugs, wands, scarves, and anything else any depressed muggle would want to brighten up their banal, magic-free lives. Put your red sox on Whether you're a baseball fan or not, the Boston Red Sox is arguably one of the most famous bat/ball teams in the world. In the last twenty years, they've won the World Series four times, and every year, rabid fans gather around Fenway Park to cheer them on. So, why not go grab some sweet Red Sox memorabilia during your trip? The team store contains loads of great baseball content, like jerseys, baseballs, hats, yearbooks, and collecting cards. Even if the stadium doesn't interest you, you'll find plenty of vendors around the city proudly displaying their wares. Bunker down One of the most famous battles of the War of Independence took place at Bunker Hill. So you can bet your bottom dollar that there's a shop full of memorabilia for you to purchase. Located off of the Freedom Trail, the Bunker Hill Monument has its own gift shop, where you can pick up Bunker-related souvenirs and other oddities dedicated to both the battle and Boston itself. So, have at it. Also other sports things! Besides the Red Sox, Boston has a handful of other famous sports franchises that call it home. At the TD Garden, you'll find shops dedicated to both the basketballing Boston Celtics, and the hockey-pucking Boston Bruins. So go pick up a t-shirt, hat, or jersey and wear them with pride. So what if you're not from Boston? Who's going to stop you? No one, that's who. J R R Token When visiting Boston, chances are you'll take the subway at one time. But long before the advent of contactless cards and digital ticket readers, Bostonites used something else to get through the gates. That's right, people, we're talking about subway tokens. So why not commemorate your vacation and pick one up for yourself at the MBTA gift shop? Sure, it might be a useless sliver of finely crafted metal now, but boy does it tell a story. A story of how people used to pay to ride the subway. They even sell other subway-related memorabilia like toy subways. Perfect for kids who just can't get enough of riding the subway trains. Kids, ey? Easily pleased. Harvard? I hardly knew...ard One stop on your Boston tour should be the city's famous Harvard University. Not only can you take a tour of the facilities with a real, authentic, 100% human student, but you can even visit the campus' rather fantastic Natural History Museum. But why would anyone believe you even went without any proof? Well, don't worry about that; just pick up some sweet Harvard threads and other things at the Harvard Shop! Yes, even you could pretend you attended Harvard by buying a sweet hoodie, or sports-related jacket. Then, use what you learned on the tour to convince others that, yes, you were worthy to walk its halls and learn many things about things. Luck of the Irish Do you ever wonder whether you have too few Irish things in your abode? Need a little green to add to the sheen? Well, guess what? You can do it! Simply head on over to one of the many Irish-themed souvenir shops you'll find in the city. Our recommendation is Southie's Own on W Broadway, where you'll find plenty of delightful Irish oddities to purchase with real money. Do you like Shamrocks? They sell many things adorned with the sprig, including hats. They also sell flags. These should suffice. In the Beantime Baked beans. Love them or hate them; they do exist. We can prove it! Boston is even called Beantown because they became a staple for settlers of the New World. See, proved. And, if you're visiting Beantown, sorry, Boston, then why not pick up the town's modernized take on the humble bean? Nothing quite says America like adding sugar and meat flavors to a healthy legume. These delicious treats are worth the investment, and will be the perfect gift to any friend you'd like to confuse. So go on, get beany with it! Sorry. That was inappropriate. Adamized And finally, let's end with one of Boston's most famous exports; beer! You may have heard of a little brew called Samuel Adams? Well, that tasty treat is based in Boston, so why not buy a t-shirt or other form of clothing that celebrates the suds at the brewery's gift shop? They do hats, beer, coasters, beer, shirts, and even beer. So what are you waiting for? Thanks for reading the menu; hopefully, it helped you discover the best Boston souvenirs. Looking for more Boston fun? Here's our guide to the best times to visit the city! But what if Boston isn't safe? Well, you can find out if it is right here (spoiler alert: it is).
Dom Bewley
Boston Skyline
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Wednesday in Boston: Must-See Spots and Hidden Gems

Exploring Boston on a Wednesday? Here’s how to make every minute count!

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