Five Reasons to Leave the House This Weekend

Hang out with The Roots, sip some wine, and swim with the sharks.

Food & Drink
Taste of WGBH: Food & Wine Festival

WGBH isn’t just Boston’s premiere public radio station. The folks over in Brighton also know how to party. Kick off your weekend early and stop by their gala tonight, where 25 of Boston’s best chefs will have their own tasting stations set up. If you’re feeling more pinot noir than roasted duck, there will be a wine auction with all proceeds going to charity.

Price based on individual events, Thursday, September 19, to Sunday, September 22, WGBH, One Guest St.,

Life Is Good Festival

Boston Calling might have been the buzz of the town, but let’s not forget that the Life Is Good Music Festival has been delivering good vibes and fun times to Boston since 2010. This year’s lineup is their best one yet with Hall and Oates, The Roots, and Jack Johnson headlining for the weekend. Other festival activities include sack races, seed spitting competitions, and a BMX bike show. 

$65 per day, Saturday, September 21, to Sunday, September 22, Prowse Farm in Canton,

TD Bank Mayor’s Cup Criterium

It’s no Tour de France, but it’s the closest that you can get in Boston. The TD Bank Mayor’s Cup is an annual race located at City Hall Plaza, where you can watch cyclists ride at speeds up to 45 mph around the narrow downtown looped course. There will also be a competition for children ages 3-9, along with a race among Boston’s team mascots such as the Celtics, Red Sox, and Bruins.

Free, Saturday, September 21, 11 a.m., City Hall Plaza,

Boston Sharkfest

The Charles River is officially clean enough to swim in for the first time in 50 years, which means that open water swimming events are popping up everywhere. The Boston Sharkfest is a 1500-meter swim from East Boston to the South Boston Piers. Contrary to its name, there aren’t actually any sharks involved in the race. Apologies to Bear Grylls. Spectators can view the race from Piers Park.

Free, Saturday, September 21, 12 p.m., Piers Park,

Street Fair
Allston Village Street Fair

Only in Allston can you party it up with lacrosse bros and finish off your night with some Stoli and bulgogi. This weekend, head over to the Allston Village Street Fair and enjoy the congregation of weirdness on Harvard Ave. There will be appearances by American Idol’s Ayla Brown, Miss Teen Massachusetts, and numerous performers. 

Free, Sunday, September 22, 12 p.m., On Harvard Ave. between Cambridge St. and Brighton Ave.,