8 Ways to Spend Labor Day Weekend in Boston
Last updated: August 2024
Fall is right around the corner, and with it comes the arrival of our last long weekend until the holidays—Labor Day. This year’s day of recognition for all the hard workers out there falls on Monday, September 2. It provides the perfect chance to explore the city and dive into its historical happenings, activities, and other interest points for a leisurely day about town. Since most will have the day off from work, take advantage of this rare free time. Explore the best of New England for the fall three-day weekend with eight things to do during Labor Day weekend in Boston.
Indulge in Dining Fun
A holiday weekend calls for indulgence as soon as you slam that laptop shut. Fratelli offers a Rush Hour special every Monday, with a four-course meal available from 4–6 p.m. to beat the traffic. An appetizer of choice and pasta are followed by a selection from four main courses, including chicken, salmon, steak tips, and braised short ribs. Don’t forget dessert.
Catch Open Newbury
On Sunday, September 1, catch one of the last days of Open Newbury before its pending winter dates. This Bostonian tradition turns the Back Bay commerce street into a car-free, pedestrian-friendly walkabout from 10 a.m.-8 p.m. for several consecutive summer Sundays. Stroll through the brownstone buildings for the city’s premium dining, shopping, and leisure, and take advantage of the fall season across its eight blocks. This is the time to enjoy major name-brand retail experiences and unique Boston outposts, like Boston Olive Oil Company and Newbury Comics.
Cultural Outings
Once again, the Institute of Contemporary Art (ICA) in Boston is offering special Monday promotions for Labor Day by way of free admission. The museum is usually closed on Mondays, making this an exclusive can’t-miss event. Enjoy past and current exhibits from 10 a.m. - 5 p.m. This is the last chance to see Hew Locke: The Procession, a lifelike sculpture march depicting British colonialism and Caribbean culture. Guests can also view the last days of the muted and swirling masterpieces of Dominican painter Firelei Báez.
Listen to Jazz
Speaking of music, the weekend before Labor Day brings the 14th annual Jazz Festival back to Maritime Park in Boston’s Seaport District. Over the years, the festival has seen over 70 of the city’s finest jazz musicians hit the stage, and this year is no exception, with nearly 100 artists featured in the lineup. A beer garden and various vendors will also be onsite to participate in the fun. Hours run from 12-10 p.m. on August 30 and 31, and admission is free.
Spend Time By the Water
The harbor isn’t the only way to see aquatic splendors. The New England Aquarium houses thousands of animals as part of the city’s efforts to conserve wildlife and protect the ocean. A wealth of exhibits awaits that expand beyond the ocean itself, like the Amazon Rainforest and its tropical guests or the Penguin Colony with over 50 penguins. Visit from 9 a.m.–6 p.m. on Labor Day Monday, with other daily times available.
See Fireworks
On Thursday, August 29, Boston Harbor Now invites the public to Illuminate the Harbor with the 10th anniversary of its illustrious fireworks celebration in partnership with the City of Boston and Atlas PyroVision and supported by Meet Boston. Starting at 8:30 p.m. and free for everyone, the fireworks celebrate public events that the city has thrown throughout the year. Take advantage of other waterfront activities that the city provides, like the Encore Boston Harborwalk and its splendid views.
Grab a Water Shuttle
Boat trips are the preferred method of transportation for the city of Boston, and taking one to Encore Boston Harbor for the day is worth the trek across the waves. These luxury motor yachts are complimentary and leave from Long Wharf Harbor. Come by to enjoy an afternoon weekend at Cheese Meet Wine, a happy hour at Mystique, and dedicated casino time to experience the thrill of winning before hopping back on the shuttle to head back to the city proper.
More Can't-Miss at Encore Boston Harbor
Special offerings are available all around the property for Labor Day and beyond. On the rewards side, eligible participants can sign up for the Hero Program and receive a complimentary Platinum Tier upgrade, including 10x multiplier bonuses, retail and select dining discounts, and priority access to event entry and promotions. Don’t forget to reward that hard work by taking advantage of hotel room deals, such as the Bed and Breakfast for Two with an in-room breakfast credit, and other Wynn Rewards member deals.