10 Actually Fun Things to Do in Boston This Weekend

Oktoberfest two ways plus the Fluff Festival’s sticky return.

Okay, so yes, summer officially ended this week. But we could care less—cool mornings and warm afternoons are totally our jam. Which is why we’re so excited to get out and about this weekend (sporadic rain forecasts be damned). The Fluff Fest is back, for starters, and the city is fully awash in Oktoberfests. You should also check out a South End dance crawl, drop by a drag brunch, and indulge in a one-time-only lobster taco to celebrate National Lobster Day. Here is everything you must do in Boston this weekend.

Ride the sugar rush at the “What the Fluff” Festival

Friday, September 24 - Sunday, September 26
Union Square
Our most beloved food festival is back, bigger and better than ever. Now in its 16th year, this edition’s theme is “Sweet 16: Onward & Fluffward.” Plan to eat, play, and pretty much bathe in the glorious, sticky spread as Union Square restaurants and businesses celebrate Somerville’s greatest invention.
Cost: Admission is free; vendor prices vary

Spice up your weekend at Urbanity Dance’s dance crawl

Friday, September 24 - Saturday, September 25
Urbanity Dance
The South End dance studio has no interest in being ordinary. Case in point? It’s kicking off its 10th anniversary season with Go stop listen. Still wait go, a roving performance where small audience groups ranging from one to six people are taken to ten different locations through the area to see dance vignettes set to original scores by Boston-based artists.
Cost: $25

Raise a stein at Lamplighter Oktoberfest

Friday, September 24 - Saturday, September 25
Lamplighter Brewing Co.
It’s the most wonderful time of the year. Lamplighter celebrates the autumnal ritual with pours of its own Oktoberfest Lager paired with Brato’s Bavarian-inspired menu, which includes Bratwursts, Giant Pretzels, and German Potato Salad. Free beers will be awarded each day to the 10 best dressed customers, but even if you don’t win, the entrance fee earns you your very own 16-ounce stein to take home.
Cost: Admission runs $10 per person; menu prices vary

Keep the “prost” times rolling at Distracted Oktoberfest 2021

Saturday, September 25 - Sunday, September 26
Distraction Brewing Company
We told you—it’s the most wonderful time of the year. The Roslindale brewery is raising a stein with its very own Oktoberfest offering (except ample notes of caramel), Sausages and Sauerkraut from Urban Hearth, and Eastern Standard Pretzels served with housemade beer cheese or mustard.
Cost: No cover; menu prices vary

Celebrate National Lobster Day with the limited-edition YDT X BC Lobster Taco

Saturday, September 25
Yellow Door Taqueria & The Barking Crab
We don’t generally acknowledge food holidays… Except, of course, our favorite food holiday of the year. Yellow Door Taqueria and The Barking Crab are joining forces to offer a one-day-only taco made with fresh lobster, avocado mayo, celery, jalapeno, lime juice, and shredded lettuce, served in a fried handmade corn tortilla. The $34 creation is huge, indulgent, and only available while supplies last.
Cost: No cover; menu prices vary

Toast one a local icon at Hood’s 175th Anniversary Celebration

Saturday, September 25
Hood Park
All we can say is, we hope they’ll be making Hoodie cups for another 175 years. In the meantime, celebrate Hood’s achievements at a daytime bash featuring complimentary food from Charlestown mainstay Tradesmen, additional treats from Boston food trucks, live entertainment, lawn games and, but of course, Hood treats galore.
Cost: No cover; vendor prices vary

See the weekend off in style at Queer Me Out Brunch with Big Freedia

Sunday, September 26
W Boston
It’s a little different than you might expect: Big Freedia, AKA the Queen of Bounce Music, is taking the stage as a part of the W Hotel’s speaker series celebrating the LGBTQ+ community. After posing for photo booth shoots, she’ll speak with moderator Jonny Minogue and then answer questions during the audience Q & A. Rest assured that all your favorite brunch goods will still be represented.
Cost: Tickets start at $5 per person

Explore the long-awaited Hub Hall

Friday, September 24 - Sunday, September 26
North End
It’s finally here: the answer to all your pre-game eating dilemmas. Located just steps away from the TD Garden is a food hall populated by 18 new eateries, from Lily P’s Chicken & Oysters to Cusser’s to APizza, Douglass Williams’ long awaited venture into New Haven-style pies.
Cost: No cover; vendor prices differ

Milk these warm fall days at the Brattle Street Beer Garden

Saturday, September 25
Alden & Harlow
Let’s all stop traffic. Every Saturday this fall, Harvard Square’s Brattle Street will shut down between Church and Elliot Streets so that Alden & Harlow can continue its outdoor takeover of Harvard Square. Expect a rotating selection of local brews, fall-friendly wines by the glass, cocktail specials, and seasonal dishes like warm rye pretzels, fried shishito peppers, and deviled eggs.
Cost: No cover; menu prices vary

Turn the camera back on yourself at Selfie WRLD Boston

Friday, September 24 - Sunday, September 26
Assembly Row
Because everyone is tired of photos of your cat (seriously). Bank some charmingly bizarre selfies at a series of whimsical, G-rated art installations (we call dibs on the slinky room) that will inject much-needed color into your fall IG stories.
Cost: Tickets run $25 per person

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Meaghan Agnew is a September gal through and through. See how she flits through the month by following her on Instagram.