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
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
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
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.
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
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
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
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.