As the heat of summer fades and the air turns crisp, Pittsburgh comes alive with the colors and charm of fall. Whether you call the city home or are just stopping by, this season brings the perfect mix of vibrant views, seasonal events, and cozy ways to enjoy the cooler days. If you're looking to dive right into the autumn spirit, here are some events that can kickstart the fall season.

November

Around the City:

Pittsburgh Wine & Spirits Festival
November 7 | Rivers Casino
At this years Wine & Spirits Festival, explore over 200+ drinks, as well as shopping exclusive selections, a buffet dinner, and complementary parking at Rivers Casino Garage! This is a 21+ event.

Pittsburgh Pet Expo
November 7 - 9 | David L. Lawrence Convention Center
Ready for the biggest pet event in the 412?! Come check out the Pittsburgh Pet Expo! There is everything from a reptile experience, photos with Santa, and a Dachshund race!

Jonas Brothers
November 12 | PPG Paints Arena
Relive your childhood and go to see the Jonas Brothers at PPG Paint Arena! It's the perfect way to celebrate the middle of the week!

Light Up Night
November 22 | Downtown and the North Shore
Highmark Light Up Night is returning for the 63rd year. Watch from downtown or the North Shore to see the city light up!

Dazzling Nights Pittsburgh
November 28 - January 3 | Pittsburgh Botanic Garden
Enjoy a walkthrough experience to kick off the holiday season! Plus, enjoy live entertainment all night long!

Heinz Chapel Choir Holiday Concert #1
November 29 | Heinz Chapel
Immerse yourself in an experience like no other: The Heinz Chapel Choir's first concert this holiday season. Whether you love choir music or it's your first time, relax and enjoy the amazing music you're about to witness.

At Bakery Square:

Yoga in the Portal
Every Saturday | The Portal
Join us for a serene escape at The Portal in Bakery Square every Saturday. Find your inner peace and rejuvenate with our weekly yoga session. Namaste!

Page Turners Book Club
November 2 | Conservatory
Discover, discuss, and connect with fellow book lovers at the Page Turners Book Club hosted by @pghgoodreads! Munch on delicious food while chatting about your favorite reads. Enjoy awesome vendors and fun activities each month!

The Assembly: A Vintage Makers Market
November 16 | The Portal at BKSQ
Discover unique handcrafted goods and timeless treasures from local artisans and vintage vendors in The Portal at Bakery Square.

The Enchanted Royal Ball
November 15 | The Portal
You are formally invited to the Royal Ball! Join us for a fairytale celebration alongside your favorite royal couples and beloved princesses. You must purchase a ticket prior to the event.

Modern Calligraphy & Holiday Place Card Lettering with Sip & Script
November 23 | The Conservatory
Join us in the Conservatory for pretty lettering by Sip & Script! Whether you're a stationery nerd, DIY Bride-to-be, or just a crafty individual, you'll be introduced to modern calligraphy with a pointed dip pen and ink in this workshop.

Jordan Millington Liquorice Art Unveiling
November 24 | The Portal
Join us for the sixth exhibition at THE PORTAL Art Gallery in Bakery Square, featuring new works by Jordan Millington Liquorice. Enjoy an evening of art, music, light bites, and drinks as we celebrate this exciting new collection.

Takos & Trivia
Every Tuesday | tako torta
Grab a marg and take a seat because trivia is getting SPICY! Trivia is hosted by the amazing minds at Buzzworthy Pub Trivia. Join from the bar, the jungle, the lounge, anywhere in the restaurant! All questions are posted on the big screens so you can play along wherever you are.

Find more November events at BKSQ here.

October

Around the City:

Autumn Serenade Luncheon Cruise and Tour
October 1, 4, 15 & 18 | Gateway Clipper
Join in for an autumn cruise on the Gateway Clipper! Enjoy a buffet lunch, a full-service bar, photo ops, and live entertainment by Drew Sipos.

Oktoberfest Pittsburgh
October 2 - 12 | Ft. Duquesne Blvd & Sixth Street Bridge in Downtown Pittsburgh
Oktoberfest is back in the 412! Join in on the fun October 2 through 12 in Downtown Pittsburgh and drink all the beer you can handle! Plus, listen to live music and cheer on the competition in the annual Stein Holding contest.

Spritz & Stroll
October 4 | 5438 Walnut Street, Shadyside
Take a stroll through Shadyside while sipping on your new favorite cocktails. Plus, shop autumn vendors, custom fall bouquets, play cornhole, and so much more! And make sure to grab a bite to eat at Cousins Maine Lobster Truck.

Fall Flower Show: Visions of Japan
October 4 - 26 | Phipps Botanical Gardens
Visit Phipps for a whole new experience surrounding chrysanthemums in Japan! The new exhibit is meant to highlight the connection between humans and the nature that surrounds them. Be sure to attend before the show is over!

Monster Murder Mystery
October 10 | Kamin Science Center
Looking for a spooky evening? Kamin Science Center is hosting a Monster Murder Mystery for guests 21 and up using real forensic techniques all while sipping on a cocktail!

Pittsburgh Coffee & Chocolate Festival
October 25 & 26 | Monroeville Convention Center
The Pittsburgh Coffee & Chocolate Festival is here! This event is meant to expand your knowledge of both coffee and chocolate (all while you have the pleasure of enjoying them both). Explore local coffee shops, roasters, bakeries, and more!

At Bakery Square:

Yoga in the Portal
Every Saturday | The Portal
Join us for a serene escape at The Portal in Bakery Square every Saturday. Find your inner peace and rejuvenate with our weekly yoga session. Namaste!

Oktoberfest at Bakery Square at City Kitchen
October 3 & 4 | City Kitchen
Grab your steins, savor delicious Bavarian bites, and groove to the oompah tunes at Bakery Square's Oktoberfest! Join us at City Kitchen for a two-day long Oktoberfest celebration. Come in your best lederhosen and celebrate German tradition in style!

Page Turners Book Club
October 5 | Conservatory
Discover, discuss, and connect with fellow book lovers at the Page Turners Book Club hosted by @pghgoodreads! Munch on delicious food while chatting about your favorite reads. Enjoy awesome vendors and fun activities each month!

Modern Calligraphy & Pumpkin Lettering for Beginners with Sip & Script
October 12 | The Conservatory
Join us in the Conservatory for pretty lettering by Sip & Script! Whether you're a stationery nerd, DIY Bride-to-be, or just a crafty individual, you'll be introduced to modern calligraphy with a pointed dip pen and ink in this workshop.

The Assembly: A Vintage Makers Market
October 19 | The Portal at BKSQ
Discover unique handcrafted goods and timeless treasures from local artisans and vintage vendors in The Portal at Bakery Square.

Takos & Trivia
Every Tuesday | tako torta
Grab a marg and take a seat because trivia is getting SPICY! Trivia is hosted by the amazing minds at Buzzworthy Pub Trivia. Join from the bar, the jungle, the lounge, anywhere in the restaurant! All questions are posted on the big screens so you can play along wherever you are.

Find more October events at BKSQ here.

September

Around the City:

Pittsburgh Irish Festival
September 5 - 7 | Carrie Blast Furnaces National Historic Landmark
A festival raising awareness to Irish and Irish-American culture, Pittsburgh Irish Festival is BACK for another great year! Created in 1991, the festival is celebrating its 25th year at Carrie Blast Furnaces from September 5 through 7 with authentic food, music, and more!

The Original Pittsburgh Taco Festival
September 6 | The Stacks at 3 Crossings
Like its name suggests, The Original Pittsburgh Taco Festival is back again bringing the tastiest tacos to the Pittsburgh area! There will also be face painting for the littles, as well as various activities. The festival is ticket entry only, and they should be purchased in advance.

Steelers’ Home Opener
September 14 | Acrisure Stadium
Steelers’ are ready for yet another winning season! Watch the Steelers’ in action at the home opener on September 14th against the Seattle Seahawks.

International Jazz Festival
September 16 - 18 | Liberty Ave.
The 15th annual Pittsburgh International Jazz Festival is here! Join the city for free outdoor concerts on Liberty Ave. Ticket purchase is necessary for all other events, including the Jazz Train, George Benson Tribute Concert, and Taste of Jazz.

Adam Sandler’s You’re My Best Friend Tour
September 20 | PPG Paints Arena
Just recently starring in Happy Gilmore 2, Adam Sandler is coming to Pittsburgh to perform his comedy! This event is strictly for audience members aged 16 and older, and will truly be a night you won’t forget.

At Bakery Square:

Yoga in the Portal
Every Saturday | The Portal
Join us for a serene escape at The Portal in Bakery Square every Saturday. Find your inner peace and rejuvenate with our weekly yoga session. Namaste!

Page Turners Book Club
September 14 | Conservatory
Discover, discuss, and connect with fellow book lovers at the Page Turners Book Club hosted by @pghgoodreads! Munch on delicious food while chatting about your favorite reads. Enjoy awesome vendors and fun activities each month!

Outdoor Movie Nights
September 7, 21 | Lawn
Join us in the Bakery Square courtyard for a movie night! On September 7th, watch Beauty and the Beast with us and on the 21st Twilight! Grab some complimentary popcorn, and snuggle up with a blanket on the lawn to watch the movies on the big screen. The movies begin at 7:30 pm.

Live Music on the Lawn
Every Saturday | The Lawn
Enjoy music in the Courtyard from some of the best local artists in Pittsburgh, presented by Dollar Bank!

The Assembly: A Vintage Makers Market
September 21 | The Portal at BKSQ
Discover unique handcrafted goods and timeless treasures from local artisans and vintage vendors in The Portal at Bakery Square.

Takos & Trivia
Every Tuesday | tako torta
Grab a marg and take a seat because trivia is getting SPICY! Trivia is hosted by the amazing minds at Buzzworthy Pub Trivia. Join from the bar, the jungle, the lounge, anywhere in the restaurant! All questions are posted on the big screens so you can play along wherever you are.

Find more August events at BKSQ here.