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 as well.

On Sunday, September 7, 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.

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., and they are available to reserve starting on Sunday, August 31. This is the last chance to see Stanley Whitney: How High The Moon, a color-block presentation with decades of legacy. Guests can also add a water shuttle trip onto each ticket as an optional perk. 

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.

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.

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.

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.

In the days and weeks leading up to Labor Day, casino promotions are hot and ready for the taking. Enter for a chance to win $100,000 in the Summer Spectacular cash giveaway, with up to $25,000 in winnings for a single person. From there, take a stroll around the casino to participate in slot machines, table games, and other forms of gambling fun.

To stay on theme for a historic Boston trip, a trolley tour provides a retro mode of transportation for moving around town. This Labor Day, embark on an expedition through the old town, exploring its many sites with hop-on and hop-off options that include several stops with commentary and stories. Book with a reputable company, and block out a large part of the day to see the sights.