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.,

9/20/2013: The listing for the Allston Village Street Fair has been updated to eliminate any confusion regarding as to who hosts the event.

  • Joan Pasquale

    Dear Readers,
    Please visit for correct information regarding the annual Allston Village Street Fair Festival which takes place on Harvard Avenue in Allston on September 22nd, and the AVSF Festival’s 2013 Entertainment Line-Up.
    Please note that the AVSF Festival is enjoying it’s 7th Production year, and is produced solely by Joan Pasquale, and provided to the General Public via Fundraising by The Parents and Community Build Group, Inc. all-volunteer run Community Service Nonprofit Organization based in Allston.
    Allston Pudding as an Allston based business, was invited to Book the 2013 AVSF Festival’s 2nd Stage Band Line-Up, which they’ll be presenting on September 22nd. But Allston Pudding is not responsible for the annual Allston Village Street Fair Festival’s creation, production, or fundraising to present the AVSF Festival to the General Public.
    Please visit the annual Allston Village Street Fair Festival’s Website at: for correct production and entertainment information. Please consider joining the all-ages AVSF Festival’s amenities on September 22nd in Allston, as the AVSF is always a tremendous amount of Fun, and it’s FREE!
    Thank you,
    Joan Pasquale, Executive Director/AVSF Producer
    The Parents and Community Build Group, Inc. – PCBG,Inc.
    The Ringer Park Partnership Group
    Allston Village Street Fair Festival