The Best Fall Festivals and Oktoberfests in Pittsburgh

As soon as you feel a chill in the air, it’s time to start planning autumn activities. We have you covered with apple and pumpkin picking, Oktoberfests, community farm celebrations, and more.

Sept. 14

Take part in an urban agricultural celebration of handmade, homegrown, and fermented fun at Allegheny Commons Park West on the North Side.

Sept. 14

Celebrate OCA Pittsburgh’s 50th anniversary with fall equinox with art, food, and performances in Pittsburgh’s historic Chinatown on Third Avenue, Downtown.

Weekends, Sept. 14 – Oct. 27

Go for a tractor ride with an cider slushie, pick apples and pumpkins, and dig into market food every Saturday and Sunday in Wexford.

Weekends, Sept. 20 - Oct. 6

Dance in the Troy Hill biergarten to music by Polkamaniacs 4 with a drink from the new Munich-style firkin-keg. Plus, there’s a VIP party! Pro-tip: don’t skip the beer caves.

Sept. 20 - Oct. 6

Celebrate with the ceremonial tapping of this year’s batch of beer at the Homestead Brewery — and get a commemorative boot glass for $25 (with beer)!

Sept. 21

Sample local pours, get tasty grub from food trucks like Brisketburgh and Taquitos, and jam out to live performances in SouthSide Works.

Sept. 21 - Oct. 6

Enjoy Bavarian food while sipping on the “Ordinary Things” fest lager or “Cinnamon Ghoul” pumpkin ale at Spoonwood Brewing Company in Bethel Park.

Sept. 21

Keep the festive fun going with steinholding competitions, classic food, and live music at the Highline.

Sept. 21, 27 & 28 and Oct. 4 & 5

Find Festbier, pretzels, games, and music at Lawrenceville taproom when it transforms into a festive German village.

Sept. 21

Enjoy wine tastings, food trucks, local artisan vendors, and music on Broad Street. Dogs are welcome!

Sept. 27-28

Cheers with live music, German dancing, a corn hole tournament, and more in Creighton — and don’t forget to snag your ticket now to get a complementary stein and one free lager.

Weekends, Sept. 28 – Oct. 27

Pile in for family fun, food trucks, and pumpkin picking every weekend in Finleyville.

Sept. 28

Take your pick from six sour slushies in flavors like apple cider and watermelon rancher at the McKees Rocks taproom.

Sept. 28

Head to the Highline on the South Side for beer specials, a pop-up market, Bavarian food, crafts, and a cookie table at Burghers Brewing.

Sept. 29

Bring your own blanket for a scenic sunset picnic at Kimpton Hotel Monaco's Rooftop, Downtown — complete with a personal charcuterie board and two fall-themed cocktails per person.

Sept. 29

Shop for art and all things spooky, watch live music and cultural dance performances, participate in a skeeball competition, and dig into vegan treats at Velem Fermentation in the South Side.

Oct. 3

Dust off your lederhosen for a best-dressed competition, dance to live music, make flower crowns, and drink German brews Cinderlands in Lawrenceville.

Oct. 3-13

Revel in 11 days of live music, food vendors, family activities, and a 60–foot Ferris wheel on the Roberto Clemente Bridge when the karneval and biergarten take over Downtown.

Oct. 5

Drink Pennsylvania-brewed Oktoberfest-style beers with fresh pretzels from Allegro Bakery and more munchies from Black Cat Pizza and Red Eye Bar-B-Q at Old Thunder Brewing Company in Blawnox.

Oct. 5

Savor an apple dumpling while you browse local vendors and groove to live music at the annual event in Butler County.

Oct. 5

Celebrate 17 years of Braddock Farms’ mission to provide organic local produce to the neighborhood with farm games, harvest activities, demos, and seasonal bites.

Oct. 6

Head to Armful of Flowers on Mt. Washington for a pumpkin patch, local vendor market, bouquet bar, and mini golf course. Then skip right next door to Bigham Tavern for a hot wing competition, an ax-throwing tournament, stein hoisting, and a dog costume parade.

Oct. 12

Go out for an evening of local appetizers, drinks, and art at Tree Pittsburgh’s beautiful riverside venue.

Oct. 5-27

See captivating chrysanthemum displays alongside different genres of music at Phipps’ Rhythm and Blooms event, and pick up an autumnal treat in the cafe or gift shop.

Oct. 19-20

Take a gander at gigantic pumpkins (with record weights over 2,500 pounds!), enjoy lots of activities for the kiddos, and be amazed by the colossal pumpkin drop at 3 Crossings in the Strip District.

Oct. 20

Dress up for craft beer, cocktails, NA drinks, food trucks, and fabulous drag performances at Velem Fermentation on the South Side.