10 Things to Do in Boston This Weekend!

by | Sep 16, 2022 | Boston - Experience, Dirty Water News

Looking for something fun and exciting to do in and around Boston this weekend? Want to go out but can’t find anything that is appealing to you? Looking for live music or some quality family time?  Boston has it all this weekend. There’s literally something for everyone. Take advantage of these opportunities and get out on the town this weekend!  Here are some of our top picks for the weekend of Friday, September 16h through Sunday, September 18th!

Friday, September 16 – Sunday, October 2, 2022 – 8am to 10pm

The BIG E – One of the most well-known and biggest fairs in New England kicks off this weekend! The Big E draws crowds from all over the country with its delicious food, a huge variety of rides, the famous Avenue of the States, great shopping, and top-notch music and entertainment.

This year they’re having Parades daily at 6PM.  Come line the route and enjoy the procession of High School Marching Bands, specialty floats, antique vehicles and more. See the magnificent Hallamore Clydesdales and Commerford Pony Hitch, wave hello to Shipyard’s Pumpkin Head Pete, try your luck at catching a few beads from the Mardi Gras revelers and dance to rockin’ tunes.

Friday, September 16 – October 23, 2022

King Richard’s Faire – THE New England Renaissance Festival is long considered THE premier Fall entertainment event of the region!
Entertainment, exciting rides and challenging games abound on the Faire’s enchanting 80-acre wooded site. There is no doubt you’ll be enthralled by the minstrels, acrobats, fire eaters, aerialists, and larger than life-size puppets. Get ready to be dazzled by two all-new Dog Shows! Where you’re sure to witness some truly captivating canines!


Hundreds of talented performers entertain our patrons continuously throughout the day when visiting any one of our eight vibrant stages. The King’s handsome knights battle on horseback as bawdy beggars compete in mud. Happy villagers engage you in the lanes and frolicking faeries can be seen dancing through the forest. Make sure to test your skill in his majesty’s Gaming Glen.

Saturday, September 17 & Sunday, September 18, 2022

Trillium Oktoberfest – Join Trillium Brewery for a festive weekend in Canton, Fort Point, Fenway, and Greenway celebrating Oktoberfest with lederhosen, lagers, music, and German-inspired food specials! All ages welcome & no RSVP or tickets required.
Click here for more details.

Trillium Brewing Company is a New England farmhouse-inspired brewery with locations in the Fort Point and Fenway neighborhoods of Boston, as well as in Canton, MA.

Saturday, September 17, 2022 – 3-7pm

WHAT THE FLUFF FESTIVAL– 17th Annual What the Fluff? Festival:  Fluff at First Sight: Back on Track!

A tribute to Somerville’s greatest, marshmallow fluff! This event is on Saturday, September 17th from 3:00-7:00PM at Union Square in Somerville. Like Peanut Butter to its Fluff, the world can be both salty and sweet. This year’s theme — Fluff at First Sight: Back on Track — hits the streets in its traditional festival format & scoops a spoonful of Somerville to help life’s absurdities go down.

Saturday September 17, 2022 – 12-5PM

CiderFest at Time Out Market Boston – Swing by Time Out Market Boston on Saturday, September 17th for Ciderfest! Time Out Market has  teamed up with all their favorite Cider Breweries including: Citizen Cider, High Limb Cider, Stormalong Cider, Lookout Farms, Artifact Cider Project, and Boochcraft Organic Hard Kombucha to showcase the best that New England has to offer.

Jump into the flavors of Fall with live music, free samples, and a chance to win a special barrel aged High Limb Cider! Every time you buy a glass of their specialty cider you get an entry into the raffle. This event is free to attend, must be 21+ to sample ciders.

Saturday, September 17th, 2022 – 9:30-11PM

DANCING ON THE CHARLES Outdoor Dance Party – The music is gonna be bumping. The dance floor is gonna be moving and DOTC cannot wait to see you THIS SATURDAY!  Come jam (and dance, of course) to the following schedule:  9:30pm-11:00pm – Hot Pot (BOS) NV’D Records, Holy Ship 13.0 – 8:00pm-9:30pm- DJ Bruno (BOS) Utopia Boston – 6:30pm- 8:00pm – Adam Gibbons (BOS) Uhuru Afrika –  4:30pm-6:30pm- GMGN (BOS) – 3:00pm- 4:30pm- Joe Tagessian (BOS)

21+ event w/ valid ID – No Outside Beverages allowed in! Food to purchase by Katered by Kiara – Come hungry and support this local vendor! food (food served around 6:30pm) CASH BAR!! CASH BAR!! CASH BAR!!

Sunday, September 18th, 2022 – 11AM to 5PM

Boston Food Festival – The Sustainable Business Network of Massachusetts (SBN)  recently announced that the 12th Annual Boston Local Food Festival will be held on September 18th, 2022 on the Rose Kennedy Greenway. Bring your family and friends to eat, shop, and discover local tastes from New England. This annual Boston Local Food Festival has been hailed as one of the top 10 food events in Boston since 2010.

Come enjoy shopping, sampling, and demonstrations with local food businesses like: Cape Cod Howlin Hot Sauce, Craic Sauce, C.R.E.A.M., Crooked Stick Pops, Edible Boston, Eloti Street Corn, Fork on a Road, Ginger Gems, Goodie Crunch, Hometown Poke, Kays Curries & more!

Sunday, September 18, 2022 – 1-5PM

2022 Mystic MusicFest – Are you ready for some live music in Medford? Come join the fun on Sunday, September 18th from 1-5pm at the Condon Shell on the fabulous Mystic River in Medford (2501 Mystic Valley Pkwy) for a free, family-friendly concert. For the first time, they welcome a BEER GARDEN provided by Medford Brewing Company!

1pm:  Tilt-a-Whirl is a great band from the North Shore playing 50/50 covers & original songs! – 2:30pm:  Spittin’ Vinnies – the band that plays all the songs you know by heart and featuring Mystic Music Fest organizer, Russ Robar on trumpet. They will be playing originals ‘Drink to Boston’ and ‘Stripes Can Dance’! You’ll soon know the words to these songs too and be singing along! – 4pm-the Porter Squares – playing originals and some great lesser covered covers. There will be chair massages provided by licensed massage therapist by Janine Robinson from 2-4pm. $20 for 20 min – cash only!  This is a rain or shine event.

Sunday, September 18, 2022 – 7:30 PM – 9:00 PM EDT

Comedy at King’s – Come experience the country’s funniest stand-up comedians, right in the heart of Boston’s bustling Back Bay neighborhood! Named a “Critic’s Pick” in the Boston Globe, King’s shows regularly feature headlining performers who’ve appeared on Netflix, Comedy Central, and HBO, to name a few.

Offering a delicious dinner menu, top-notch selection of craft beer and unique cocktails, King’s Backstage provides a vibrant & friendly atmosphere that’s perfect for date nights, work outings, and meet-up’s with old friends.  The comedy is free, all you have to do is register here!

Sunday, September 18, 2022 – 10AM – 2PM

Touch a Truck at Suffolk Downs – Don’t miss this family friendly event at Suffolk Downs!  Join the local community at Touch-a-Truck at The Track on Sunday, September 18th from 10am – 2pm at Suffolk Downs.

Walk along the track for an up-close view of tractors, trucks, diggers, police cars, and fire engines. Sit in the seats, honk the horns, or take your picture on the front end! Enjoy kids activities, games, giveaways, food trucks, and craft beer by Rockport Brewing in the Paddock! This event is free to attend and open to the public.  Registering by clicking here is recommended.