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

By Katie Sagal

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

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

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Acorn Street in Beacon Hill, Boston
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Boston Airport to City Travel Options (Logan)

Baked beans, the Boston Red Sox and thr bar ‘where everybody knows your name’: Massachusetts' lively state capital offers all this and more. Known as the birthplace of the American Revolution, this is a city that’s thoroughly steeped in history. Follow the Freedom Trail to immerse yourself in 250 years of US heritage, step inside the former home of legendary revolutionary Paul Revere, and take a trip to Louisa May Alcott’s house in Concord, where her literary masterpiece Little Women was both written and set. With all this on offer, you’ll no doubt want to get to the heart of the city (and those umami, smoky platefuls of sweet-savory beans) as quickly as possible after touching down at Logan Airport. Read on for our guide to all the transit options from Logan to downtown Boston… Boston Logan International Airport in Brief There’s only one international airport in Boston. So the chances of getting yourself lost are fairly slim. Unless of course you accidentally boarded a flight to Boston in England, but that’s for another blog… In-keeping with Boston’s proud history, Logan is named for local son Edward Lawrence Logan: judge, lawyer, politician and military officer. Indeed, the airport’s full name is General Edward Lawrence Logan International Airport. A bit of a mouthful, we’re sure you’ll agree, which is why it’s commonly known as plain Logan. The airport serves as the primary global gateway for Massachusetts and New England, with over 100 domestic and international routes. Around 40 million passengers pass through every year. Best of all, Logan lies just 5km east of downtown Boston, straddling the border between East Boston and the town of Winthrop. In light traffic, the cab ride into town can take as little as 10 minutes. So, without any further ado, here’s how to get from Logan Airport to downtown Boston. Logan Airport to Downtown Boston by Public Transport On-Airport Shuttle System It’s likely you’ll make use of Logan’s free shuttle system, which serves all four terminals and shuttles excited new arrivals to the Rental Car Center and parking garages. The shuttle also serves the airport's subway station and water transportation dock for onward travel to downtown Boston, via Massachusetts Bay Transportation Authority (MBTA) services. Getting from Logan to Downtown Boston by Subway Having shuttled your way successfully to Airport station, it’s just a hop and a skip along the Blue Line to downtown Boston. The Blue Line connects to the Green Line at Government Center station and to the Orange Line at State Street.  Going anywhere near Back Bay, Fenway Park or Boston University? The Blue Line out of Logan is your friend. A one-way ticket costs just $2.90, and you can transfer between subway and Silver Line, Express and local bus services twice on your ticket, paying only the one-time cost of whichever service costs more. Getting from Logan to Downtown Boston by Bus Bus enthusiasts rejoice! There are multiple ways to get from Logan to downtown (and beyond) on four wheels. The MBTA’s Silver Line connects all terminals at Logan to South Station and beyond. Hitch a free ride on SL1 as far as South Station if you want to transfer to the subway’s Red Line here. Services SL2, SL3, SL4 and SL5 continue to other areas of Boston and a one-way ticket costs $1.70. Alternatively, the Express buses speed visitors to downtown and beyond for $4.25 one way. There are also multiple private bus services covering much of New England and New Hampshire, from reputable companies including Concord Coach Lines, Boston Express Bus and more. Getting from Logan to Downtown Boston by Ferry Ok, it ain’t Venice, but arriving in Boston by sea is certainly the most scenic of all the airport transit options. Take the short trip across Boston Harbor to Long Wharf for rapid access to downtown, taking in panoramic views of the skyline from up on deck as you go. The On-Airport Shuttle connects terminals to the water transportation dock and the terminals, and a one-way ticket on the MBTA ferry costs $2.40 Top Tip: CharlieCards and CharlieTickets Charlies are reusable cards or tickets that can be preloaded with cash and used to tap in and out of MBTA subway, bus and ferry services. They’re a good option if you plan to use public transport a fair bit while you’re in town, as there are savings to be made over buying individual tickets for every journey. CharlieTickets are particularly convenient for visitors. You can pick yours up at vending machines in the airport and most stations. Logan Airport to Downtown Boston by Private Transfer Cabs are readily available outside arrivals at terminals A, B and E and on the ground floor of the terminal C parking garage. It’s only around 5km from the airport to downtown Boston but travel times and prices can vary wildly depending whether you’re traveling in rush hour traffic or not. Expect to pay somewhere in the region of $40-50 one way. Ride apps like Uber and Lyft will usually cost a little less, but you’ll have to arrange these yourself and organize a suitable pick-up point. Alternatively, make like your favorite Bond villain and charter your own pre-booked private limousine. Or hop in a water taxi: one-way tickets from companies including Red Top Boats and the Boston Water Bus start from around $15. Logan Airport to Downtown Boston by Rental Vehicle Boston’s walkable downtown and excellent public transport system means you’ll have little need for your own wheels unless you’re planning out-of-town day trips to the likes of Salem, Portland and the Gilded Age mansions of beautiful Newport. You’ll find all the usual suspects at Logan’s Rental Car Center (RCC): everything from Alamo to Zipcar. The On-Airport Shuttle whisks passengers to the RCC via routes 22, 33 and 55, with services running approximately every 5-6 minutes. Save on attractions, tours and activities 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 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
Public park in Boston with a walking trail
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Best walks in Boston

On your marks, get set... walk! That’s the way to do Boston, anyway. Unassuming, academic and full of history, this city is the ideal place to stretch your legs as it’s also very accessible, very flat, and very pretty. There’s a good mix of city lights and green spaces, and the Charles River winds serenely on its way to Massachusetts Bay offering lovely walks along the esplanade. Beware the weather – the icy wind off the Atlantic can make things pretty wet and chilly in winter – but don’t let it put you off! Fuel up on some Boston baked beans, grab your raincoat and try out one of these awesome Boston walks: The Freedom Trail Financial District to the Theater District The Movie Mile Harvard to MIT The Battle Green Tour The Emerald Necklace Trail The Freedom Trail Many key events of the American Revolutionary War took place in Boston, and a lot of these historical sites are now accessible to visitors. To make it easy, 16 of them are connected by the 2.5-mile Freedom Trail which runs from Boston Common to Bunker Hill. It’s marked by a red path on the ground so you can’t really get lost – but if you’re finding all the history a little disorientating then use your pass to take a Freedom Trail Foundation guided tour. It covers 11 of the 16 sites on the trail, including Massachusetts State House, the USS Constitution and the site of the Boston Massacre. Your guide – complete in 18th century costume – will share all the stories of revenge and revolution so you won’t get your dates and declarations in a tangle. The Financial District to the Theater District This easy walk gives you a great overview of the modern and historic side of Boston in just a couple of hours. Start at the World Trade Center bus stop and enjoy the view of the wharf and Congress Bridge before exploring the financial district. Here, as well as being able to witness Boston’s buzzing economy in motion, you’ll find the Boston Children’s Museum, the Boston Tea Party Museum, King’s Chapel and Burial Ground and the Irish Famine Memorial. Soak up the history, then go for some retail therapy at Downtown Crossing before heading towards the Theater District via Washington Street and Tremont Street. This route will take you past Chinatown, which makes a colorful diversion if you’re feeling peckish, and you’ll come out by the Shubert and Wang Theaters. From here, it’s an easy saunter to Boston Common, where you can either have a look around Emerson College Campus or just flop down on the grass and give your legs a rest. The Movie Mile Many of Boston’s iconic landmarks are familiar to us because we’ve seen them so often on film and television – so why not get to know them in person? Take the Boston Movie Mile Walking Tour with Go City and discover over 30 locations you may have seen in films like Ted, Good Will Hunting and The Departed, or TV shows like Ally McBeal and Cheers. You’ll take in quiet, unassuming neighborhoods, historic homes, the original Cheers pub and the bench where Robin Williams and Matt Damon shot one of their most famous scenes. Make sure your big and small screen trivia knowledge is up to date, as your guide may just quiz you along the way! Harvard to MIT This is a great walk that combines two of the city’s most famous institutions with a generous taste of student life in the city. North of the river in Cambridge, these two academic heavyweights are only a mile or so apart, but a slightly detoured route will also take you past Harvard Stadium (home of the New England Patriots until the 70s) and Harvard Business School. Explore Harvard Square on your own or join a guided tour, then head west over the Anderson Memorial Bridge towards the stadium. If you’re lucky, there might be a game going on, if not, it’s still worth a wander around. From there, turn down Harvard Way past the Baker Library to the Business School, and then circle back to the river and use the Western Avenue Bridge to cross back over. Turn left and walk along the river to Magazine Beach, then head east towards MIT. If you need more intellectual inspiration, you can take another guided tour, or check out the List Visual Arts Center. The “Let it Begin Here” Battle Green Tour Take a deep dive into American Revolutionary History with a guided tour of Lexington Battle Green, included with your Go City Boston Pass. This small area is of huge historical significance, being the place where the first shots of the war were fired. See the Old Belfry that sounded the alarm, the Buckman Tavern where nervous militiamen gathered the night before the battle, the Revolutionary War Monument, the Old Burying Ground and the Henry H. Kitson Minuteman Statue. Hear stories of how the battle unfolded, George Washington’s thoughts on the whole affair, and the meaning behind the famous “Stand your ground” inscription. You’ll also see some houses and other buildings dating from the same era, so you can really feel that you’ve traveled back in time. The Emerald Necklace walk A favorite among locals and visitors alike, this walk gets its name from the way it links a chain of sparkling parks and green spaces through the city. It’s a great one if you want to get away from the concrete jungle and give your legs a proper stretch – it’s around nine miles and does include some elevation, so allow up to four hours – more if you want to stop for a picnic somewhere! Start in Franklin Park – Boston’s largest, where you’ll also find the Franklin Zoo. From here, the walk takes you through the Arnold Arboretum at Harvard University, Jamaica Pond, Olmsted Park and along the Riverway to Muddy River. This route also takes you past the Isabella Stewart Gardner Museum and the Museum of Fine Arts. Continue along the long, green space that is the Commonwealth Avenue Mall all the way to the Public Garden, then either cross the suspension bridge or take the left path past the Robin Williams Memorial Bench. Finish by exploring Boston Common and be sure to take a selfie in front of Brewer Fountain! Step it up with Go City You can walk pretty much anywhere in Boston! Make sure you don’t miss anything with a Go City Explorer or All-Inclusive Pass and save on dozens of attractions around the city.
Karleen Stevens

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