Boston is kicking off Friday, May 29 on a reasonably pleasant note — partly sunny skies and a high near 68°F — but rain showers are likely after 4 PM ET, and Saturday is shaping up to be a genuine washout with gusts to 41 mph. Make the most of the dry window now.
Today’s Setup
The morning and early afternoon stay dry. If you’re planning a walk along the Esplanade, a loop through the Public Garden, or lunch near Faneuil Hall, get it done before 2 PM ET. Rain showers move in after 4 PM as a low-pressure system tracks in from the northeast, pushing precipitation chances to 60% through the evening. Northeast winds around 10 mph with gusts to 22 mph will add a cool edge to the afternoon.
Tonight’s Khalid show at MGM Music Hall at Fenway falls right in the middle of the shower window — bring a rain jacket and budget extra time on the T.
Best Window To Be Outside
Roughly 8 AM to 1 PM ET is your cleanest stretch. After that, clouds thicken and showers develop. Gardeners, this weekend is a pass — rain continues through Saturday, and the National Weather Service warns that unsettled conditions return Monday through midweek. Check outdoor gear deals if you want to get ahead on spring prep.
Rain and Wind Risk
Saturday is the real story. The National Weather Service is calling for all-day rain with 100% probability, a high of only 51°F, and north winds of 10 to 23 mph with gusts as high as 41 mph. A Wind Advisory is already in effect for northeast Massachusetts, the east coast, and the Cape and Islands. Coastal neighborhoods and harbor areas will feel those gusts hardest — use caution near open water.
Heading to the Don Toliver: Octane Tour at TD Garden on Saturday, May 30? Budget serious extra travel time — wet, gusty conditions will slow MBTA platforms and street-level crossings. You can Find tickets on StubHub or Get tickets on SeatGeek if you still need seats. Pack a Don Toliver hoodie for the walk from the Green Line; the arena will be warm, but the streets won’t be. Method Man and Redman are also at Agganis Arena on Saturday — same weather, same advice.
What To Wear Or Bring
Today: a light jacket and umbrella after noon. Saturday: full rain gear, waterproof shoes, and a warm layer — 51°F in wet, gusty wind feels significantly colder. Don’t forget kids rain boots if you’ve got little ones in tow; puddles will be deep by Saturday morning.
Comfort Food Weekend
This weekend practically demands a slow cooker. Load up a programmable slow cooker with chili or beef stew Saturday morning and let it run all day while rain hammers the windows. An enameled cast iron Dutch oven is equally great for a stovetop soup or braised beef. Need ingredients? You can order groceries on Amazon and have everything delivered before the rain gets going.
Next Few Days
Sunday looks mainly dry — a genuine relief. But expect unsettled conditions to return by Monday and continue through midweek with periodic showers and below-normal temperatures, per the National Weather Service. Mark your calendar for June 2, when the Boston Red Sox host the Baltimore Orioles at Fenway Park — we’ll have a full gameday forecast closer to first pitch. Grab Official team gear on Fanatics to show your Sox pride no matter what the skies do.
