Memorial Day Weekend in Boston: The Ultimate Staycation

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Memorial Day Weekend in Boston: The Ultimate Staycation

There’s nothing like spending Memorial Day Weekend on Cape Cod. Or is there? When you consider the drive (hello, holiday weekend bridge traffic), the iffy weather (62 degrees does not a beach day make), and the fact that every Sam, Sally and Sarah is headed to the Cape, maybe there is a better option. Let’s talk about Boston, shall we? Let’s also embrace our inner geek – just a bit – and admit that playing tourist in one’s hometown can actually be quite fun.

Legal Harborside: Photo via website.

Friday: Should the Celtics still be in the hunt, there is an “if necessary” NBA Eastern Conference Finals game scheduled at the Garden on Friday, for those who are so inclined and actually lucky enough to score tickets. For those inclined to head over the bridge – to Cambridge, not the Cape – the three-day Boston Calling Music Festival, featuring Twenty One Pilots, Travis Scott and Tame Impala, kicks off at Harvard. For a more high-brow experience, the Boston Ballet’s Rhapsody is at the Opera House, and the Boston Pops are at Symphony Hall. Should attending an actual event after working all week seem like too much of an effort on a Friday night, fear not: This is Boston. You have literally hundreds of places awaiting your arrival. Cocktails and small plates al fresco on the third floor of Legal Harborside and craft brews at the Harpoon Brewery are just two of the dozens of options in our neck of the woods, the Seaport.

Harpoon Brewery: Photo via website.

Saturday: Consider this a delicate reminder that the meaning of Memorial Day Weekend extends beyond parties and an extra day off. Take 10 minutes at the Garden of Flags on the Common to remember the service members of the commonwealth. Okay, moving on. If you haven’t partaken of the Swan Boats since you were compelled to while on a school trip, give it a shot. It really is a distinctly Boston experience. And have you ever tried a hansom cab ride around the Common? Touristy? Yup. Wicked fun? Absolutely! They queue up on Park Street, so you’re already right there. Attend to that pang in your tummy by tucking into something substantial at nearby Parish Café, Tatte Bakery or Bistro du Midi for lunch. Continuing on with our tourist itinerary, it’s off to the waterfront for a 90-minute Historic Sightseeing Cruise with Boston Harbor Cruises. If you’re so not into playing tourist, the House of Blues kicks off a street party at 12:30, but it’s country music. Does that count? Think of all the money you’ve saved by not shelling out for a hotel room. Now go spend it on dinner at that uber-swanky restaurant you’ve been dying to try, and do not feel guilty about it.

things to do in boston

The Garden of Flags on the Common (L). The Swan Boats; photo via website.

Sunday: If you’re always too busy getting ready to head back to work on Monday to really enjoy Sunday, consider this a not-so-delicate reminder that you have tomorrow off. Read the Boston Globe—all of it. Heck, read the New York Times while you’re at. Sundays are all about the socially acceptable midday consumption of alcohol, a.k.a. brunch. Thrillist’s recently updated list of Boston brunch spots will prove invaluable in making the all-important decision on where to dine. Don’t over-imbibe, because Sunday night is party time. The Social Register, in the Seaport, has a Great Gatsby party, and there’s also the Pier Pressure White Party Cruise on the Spirit of Boston. What happens at sea stays at sea, right?

memorial day weekend in boston

All aboard the Pier Pressure White Party Cruise on the “Spirit of Boston” – photo via website.

Monday: If you went to the Gatsby party or Pier Pressure, you’re likely done for the weekend. Fair enough. For those actually able to rise from the couch, the Sox are in town with a 4:05 p.m. start time against the Cleveland Indians. Way to end your long weekend on a high note. Or not…given the way the Sox have been playing.  

Boston, you’re [our] home.