Rediscover Pittsburgh
Rediscover Pittsburgh
Rediscover Pittsburgh

Giant pumpkins, Octoberfest, and a myspace themed party! Yes, those events and more make for a packed calendar leading up to Halloween!


Oct 5

Rock Steelers Style 2018: A Signature Night

Pittsburgh Steelers suit up with their families, along with American Idol Finalist Gabby Barrett, who will perform at the show. The black and gold event supports UPMC Sports Medicine Concussion Program and Cancer Caring Center. $200-$500

Oct 6

Sienna Mercato - IlTetto - Octoberfest

The rooftop bar at Sienna Mercato will be transformed into Octoberfest, featuring Sam Adams samplings, Bavarian themed food and a stein hoist competition. Enjoy the view and the beer! | 4-7pm

City Works

Celebrate Oktoberfest in Market Square with beer infused-food and Oktoberfest brews, including German lagers, along with seasonal food and craft beers. You won’t want to miss this one! | Through October 7th

Soergels Orchards

Everything is here if you want the full Fall experience: pumpkin picking, apple picking, hayrides, food, drinks, horse drawn wagon rides. Adults can enjoy the wine. The kids can enjoy the pony rides.There is something for everyone! | Every weekend in October

Oct 13

Maggie’s Farm Anniversary Party

Five is the theme as Maggie’s Farm celebrates five years of making Rum in Pittsburgh. The party will be held under the 31st Bridge. Five live bands, five food trucks, five different beers, and five different rum cocktails for only, you guessed it, $5 each! $5 adv, $10/door | October 13th | 3pm-10pm | 31st Bridge

Oct 19

Myspace Night Dance Party

Dance to your favorite music from the Myspace era at Brillobox. Get nostalgic and add some friend requests, or adjust your top 8. Either way it’s going to be lit like 2006. | Brillobox | 10pm-2am | $5

Oct 20

Monster Pumpkin Festival

Giant Pumpkins everywhere! No really, these pumpkins are biggest you’ll ever see. There’s even rowing competitions in these giant pumpkins. Not to mention, master pumpkin carving. And the coolest thing about it, giant pumpkins dropped from cranes! You have to see this in person! | Northshore | Free

Oct 26

SouthSide Creep N Crawl

The second annual bar crawl through Carson Street includes a complimentary cocktail. Are you tired of waiting in line? The ticket will get you a free entry/skip the line for passes for Foxtail, Skybar, Local Bar, Kitchen and Steel Cactus. Drink specials up to 40% off for each venue. Let the bar crawl begin! | 9pm - 2am

Oct 27

Empath's Sober Halloween Bash

Empath's 1st Sober Halloween Costume Bash! Filled with live music, a DJ, tasty house-made non-alcoholic mixed drinks, food and snacks, prizes, tarot, vendors and more!! The Shop - Homewood will be filled with vibes for a haunting, fun and social night out!


Aug 30

Heinz Field Kickoff and Rib Festival

The unofficial end of summer kicks off with five days of ribs, music, and more ribs the weekend of August 30th - September 3rd. The Clarks will headline Saturday night, and admission is free for each day. If you want to work off the food, Sunday’s activities include the Steelers 5k race, Fitness Walk, and kid’s kickoff run.

Sep 7

Pittsburgh Irish Festival-Riverplex

The slogan for the festival is “Step into Ireland,” and they mean it! If you want Irish music, food, beer, and art--you’ve come to the right place! New activities for this year’s festival include Celtic Axe Throwing, along with a Taste of Ireland, where fans can sample and purchase foods made in Ireland! Tickets- $12/Advanced

Sep 13

The Wine Opener-Cystic Fibrosis Foundation

Spend the evening at Pittsburgh’s Grand Hall at the Priory, sampling wine and spirits, with food from top local restaurants. There’s also live entertainment, a silent auction, and a wall of wine. Try them all? Yes please! Tickets-$75

Sep 21

Third Annual David Alan Fashion Show

Pittsburgh’s own entrepreneur David Alan will be showcasing his latest men’s fashion line for what is sure to be one of the biggest parties of the year. The first two years were a huge success, generating over $20,000 for the American Cancer Society. This years celeb list includes superstars from the WWE, along with Pittsburgh Steelers, who will walk the runway on Grandview Avenue on Mt. Washington. Tickets-$150

Sep 25

Justin Timberlake - PPG

JT spent his summer playing shows in Europe, and now the man of the woods returns to PPG for the second time this year. Known for his high energy performances, Timberlake will bring a full band with him, complete with a stage in the middle of the floor. We can’t stop the feeling, but we can see one of the best live performers of today. Tickets $49-$225

Sep 29

Maroon 5 - PPG

Dirty looks from your Mother! That song was inescapable during this past summer, and it’s sure to be performed when Adam Levine and company hit PPG in support of their Red Pill Blues Tour, playing classic hits along with new tracks from their sixth studio album. Great opening act alert: Julia Michaels, who scored a worldwide hit with her song “Issues,” kicks off the show. Tickets $47-$190

Sep 29

Ed Sheeran - PNC Park

The stadium lights will shine when Ed Sheeran brings his global tour to PNC Park. All he needs is a acoustic guitar and he can entertain an entire stadium, with a passionate fan base that sings along to every word. When Sheeran sings “Perfect,” he might be talking about the city skyline backdrop. Tickets $39-$119


Aug 1

Clean Cosmetics @ East End Food Coop

What's lurking in your cosmetics products? Make a healthy and clean DIY cosmetic, gain a greater understanding of product labeling, including top ingredients to avoid, and learn how to make safe and healthy consumer decisions.

Aug 5

1st Annual Pittsburgh LGBTQ Wedding Expo

Enjoy a beautiful afternoon with us at the Pittsburgh Marriott North! You & your fiancée will have the opportunity to connect with a diversity of local LGBTQ-friendly wedding professionals, meet other couples, sample food, indulge in a cocktail... and plan the details of Your Own Special Day.

Aug 12

Crosstown Cookout

In it's third year of serving up outdoor cookout realness, this epic day party is bringing you the best of summer in Pittsburgh, dahn on the Mon Warf.

Aug 16

Little Italy Days in Bloomfield

Pittsburgh is a meatball town, and this 4-day long Italian festival in Bloomfield will prove it to you. Happening through Sunday the 189h, you'll bare witness to 3 stages, 30 acts, a Bocce competition (trust us, more exciting that you think), Italian Idol, and a pasta-eating competition.

Aug 24

7 Springs Wine Festival

3 days, 30+ wineries to sample, bands *and* vendors? We're there.

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