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

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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

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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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Things to do in South End, Boston

At first thought, you might not associate Boston with art. History? Sure. Boston was host to some massive moments in US history. The landing of the Puritans in 1630, the Tea Party in the 1770s, and the beginning of the War of Independence soon after, are all massive moments for this county. Sports? Again, yes, just look at the worldwide fandom for the Red Sox and the Celtics. Art? Not so much. But you'd be wrong. Dead wrong. Boston has grown into an artistic metropolis, far from its harsh harbor roots. Especially in South End, which is now a haven for the arts. So answer us this question - do you like art? Are you planning a vacation in Boston, or simply a resident ignorant of the city's art underbelly? If you said yes, or murmured unintelligibly, then South End might be the perfect place for you! Find out why below, as we tell you all the best things to do in South End, Boston! Including: Art museums Street art SoWa Market Eateries Nights out The Art of More We've talked the talk, so let's walk the walk. Art. What is it good for? Well, having your mind opened, emotions tugged, and world views questioned! So let's talk about South End's burgeoning art scene. We'll kick things off with the Griffin Museum of Photography, which showcases works from established shot-takers, as well as up-and-coming snappers. For thirty years, it's been a great place to explore and become mesmerized by fantastic photos. The museum houses three galleries that are brimming with images. You'll also find a rotating list of exhibits, programs, and lectures throughout the year, so if you're looking for something specific, be sure to check online before you visit. Looking for a little variety in your art life? Check out the Cyclorama at the Boston Center for the Arts. The magnificent hire space sees a weird and wide variety of performances throughout the year, from local shows and showcases to traveling galleries and even markets. You never quite know what you'll find when you, unless you check ahead, of course. In fact, the Boston Center for the Arts is a great place to discover all art forms, whether it be dance, theatre, galleries, or art fairs. It houses a number of gallery spaces besides the aforementioned Cyclorama. For instance, the Mills Gallery showcases a number of contemporary exhibitions from new and exciting artists throughout the year. Going Underground One of the art world's most satirical and critical forms in the modern day is street art. From hideous tags on subway carriages, to the story-high facades on many urban buildings, it's undeniable that street art is here to stay. Just look at the popularity of genre bigwigs like Banksy, and dollar signs attributed to even his smallest works. South End has its own thriving street art scene, thanks to the small neighborhood of Ink Block. This area beneath the underpasses and bridges of the district has been transformed into Underground at Ink Block, a process that took half a decade. Gone are the run-down parking lots and abandoned areas. Now, they've been replaced with pedestrian boardwalks, dog walking spot, bike lanes, and a wealth of curated street art spaces you can peruse at your will. So go check out what's on offer, and take a look around the area while you're at it! Market delights Let's switch gears to something more marketable. That sweet wordplay is an excellent segue to our next top spot in South End, the SoWa Open Market! For over 15 years, it's been one of South End's coolest places to be. An amalgamation of local artists, craftsmen, brewers, and cooks, you'll appreciate the neighborly vibe as soon as you step foot inside. Pick up a bite to eat, grab a refreshing craft beer, and browse the myriad stalls for knickknacks, handcrafted jewelry and clothing, or just to hear some live music! It's dog-friendly too, so if your pup joins you, we're sure they'll appreciate the inevitable deluge of love and back scratches from the market's denizens. And on the first Friday of the month, the area is transformed into an art space with First Fridays. There, you'll find hundreds of artists, gallerists, and sellers showcasing great local art. If you're in the market (yes, this is a pun, and all puns are intended, whoever says otherwise is lying) for a painting or sculpture to brighten up your dour walls, then head down there and see what's going on! Eats Food now, because you're bound to get hungry after all that culture. Thankfully, South End's got you covered with some delicious choices. Check out Boston Chops for a gentrified spin on the classic steakhouse experience. Yeah, you can get any number of steak cuts cooked in any way you want and have a great time. This is a steak house, after all. But Boston Chops offers much more than that on its thorough menu. There are a host of seafood options, as well as grilled hearts, tongues, and sweetbreads for those of you who like to try new, and potentially stomach-churning, things! Keeping in line with the above is the aptly-named Butcher Shop. It's, well, a butcher's shop that's been transformed into a carnivorous paradise slash wine bar. Ever eaten a pig's head? No? Well, you can try one here. The Shops' interesting and diverse menu also offers the usual steak selection, along with cold meats, starters, and exotic eggs. It sounds like it shouldn't work. But it does. Or, if you're looking for something a little less...gruesome, try Picco, a charming pizza joint that offers a signature charred crust that absolutely must be sampled by any pizza aficionado. On top of all that, they've got a dessert menu full of homemade ice cream, and a wealth of beers on tap. Drinks Let's end this list with some sweet spots to pick up a drink or ten. Wally's Cafe is a boozer slash music venue with a focus on the Boston jazz scene. Their cocktail menu is extensive, affordable, and delicious. So why not check it out, and take in some sweet jazz while you're at it? https://thedelux.com/Delux Cafe is a great place to pick up a local craft beer at a reasonable price. It doesn't get much tourist traffic, but don't worry. The laid-back and friendly atmosphere will stop any Wild-West saloon silence scenes from occurring. And finally, Wink & Nod is your classic cocktail bar, with a great selection of classic mixes alongside pricey 'black card' cocktails that can set you back three figures. Hey, if you've got it, flaunt it! And that about rounds out our list of the best things to do in South End, Boston!
Dom Bewley
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Things to do in Back Bay, Boston

Back Bay is one of Boston's most affluent districts, with plenty of places to go and things to see. So, if you're visiting Boston and thinking of staying in the area, you'll want to know what's good. Well, we'll tell you what's good. Right here, right now. Read on, and discover the best things to do in Back Bay, Boston! Including: Trinity Church Boston Public Library The Mapparium Boston Marathon Survivor Memorial Places to eat and more! The Holy Trinity (Church) Let's start this shindig with something holy. If you want to explore a fascinating holy place, whether you're religious or not, check out Trinity Church. Even from the outside, its ornate design is mesmerizing. But step inside, and you'll be treated to a feast for the eyes. Practically every inch was handpainted, and the whole thing was overseen by prominent American artist John La Farge. From the pre-Raphaelite windows to the awe-inspiring murals, it's a great place to visit in Back Bay. The church itself does lots of community outreach, so if you're in the area on a Sunday, feel free to go to one of their services. Words are worth it Libraries are the spine of our nation. That was a book pun, and no, we won't apologize. Wordplay is one of life's many joys. And if you like wordplay, books, and libraries, then you'll love Boston Public Library! What a terrible segue! This labyrinthine monument to learning is a frequent hang spot for students and researchers. Visitors will often find students at their laptops, staring at empty word documents with tears in their eyes. But never mind them, they made their bed. Instead, get lost in its many, many aisles. You'll likely find any book you're looking for within its massive walls. But if that wasn't enough, there are also regular talks and readings held there throughout the year, and you can even get a tour of the place if you're too overwhelmed by all the learning. Map it out Mary Baker Eddy was a special person. Not only did she overcome the adversity that came with being a female academic in the 19th-century, but she wrote a groundbreaking book that kicked off the movement that we now know as Christian Science. So, why not find out more about this fascinating woman at The Mapparium? You'll walk across a bridge through the three-story, stained-glass Mapparium globe, enhanced with music and special lighting effects. It will give you a whole new perspective of Earth's geography, thanks to the concave, mirror-imaged view it offers. Explore the library, which has artifacts from her life you won't see anywhere else. You'll learn how The Mapparium was built and take a guided tour of The First Church of Christ. In the original 1894 church building, you'll find one of the world's largest pipe organs too! Image courtesy of Jesse Costa/WBUR To those we lost The Boston Marathon bombing was an event that shook the world. If you would like to pay your respects, you can visit the Boston Marathon Survivors Monument. The artist worked diligently with the families of the deceased in its design, ensuring it captured their spirit and personality. The two installations on Boylston Street are 20ft tall bronze spires that contain light-emitting glass tubes, ensuring the people taken in the bombing will be remembered forever. Where to eat You may need a bite to eat after all that sightseeing. Thankfully, Back Bay has some fantastic eateries that will welcome you with open arms. These are our favorites! If you're looking for interesting Far East dishes, then Uni will fit you like a Japanese glove. This contemporary izakaya restaurant offers a host of street food-inspired plates, as well as Japanese favorites like Sashimi and Nigiri. Take a seat beneath the dim lighting, explore the expansive menu, and find a new dish to add to your favorites! If American seafood dishes are more your thing, don't you worry. Select Oyster Bar brings New England Seafood to your table, with a Mediterranean twist to boot. While you're free to stop by for a glass of wine and some oysters, you'll be missing out if you don't hunker down for dinner. The Maine Lobster Salad is something else, and for a fish joint, they even do a mean rib eye! Speaking of rib eye, if steaks more you scene, Grill 23 is one of the best in the country. This award-winning steakhouse is the go-to site for local business meetings, so bear that in mind if you're thinking of heading there on a weekday. But never mind the white-collar hollering, sit down, stare at their table until they relent, and enjoy some of the juiciest steaks around. Where to drink Let's end this with a look at the nightlife. If you're looking for a drink or three to see out the evening, then Back Bay has many delightful watering holes, no matter your desire. Want something casual? Try The Pour House. This sports bar contains a whopping 17 TV screens, showing a variety of games throughout the week. You'll also find a wealth of affordable beers, bar food, and your standard cocktails. It may be a no-frills kind of place, but sometimes, that's exactly what you're looking for. In the mood for something slightly fancier? City Bar is an elegant watering hole located in the century-old Lenox Hotel. And, given the likes of Babe Ruth and John Travolta have graced its elegant tables at one time or another, it's the kind of pedigree that guarantees you a great cocktail and a great time. Combine that with a hefty wine list, romantic lighting, and swanky decor, and it's the perfect date spot if you're looking to impress that someone special. And finally, if you're looking for something a little louder, then you have to hit up the Bukowski Tavern. Named after famed author Charles Bukowski, who penned the likes of Factotum and Ham on Rye, among many other novels and poems, this is a Boston bar through and through. You'll find a huge selection of delicious beers, brewed both locally and abroad, some high-quality bar bites, and the kind of larger-than-life atmosphere that makes Boston the city it is! And that's our list of the best things to do in Back Bay, Boston!
Dom Bewley
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