26 cool things to do this weekend in Pittsburgh

Jennifer Baron

Published September 24, 2019


Wrap up an active September and welcome autumn at these must-do events.

Friday, September 27: Burgh Food Tour & Fundraiser at the PA Market
2-4:30 p.m.
We all love shopping in the bustling Strip District. Now you can enjoy a rare behind-the-counter look at the eateries that give this historic market district its authentic character. Discover local history as you eat your way through iconic establishments peppered along Penn, while raising funds for Women’s Center & Shelter of Greater Pittsburgh.

Friday, September 27: Governor’s Awards for the Arts Block Party at the August Wilson African American Cultural Center
4-7 p.m.
Pre-game the Governor’s Awards for the Arts ceremony (see below) at this free block party outside the August Wilson Center, where DJ Nate Tha Barber, the Funky Fly Project and Hill Dance Academy Theatre will keep things festive.

Gallery Crawl

Photo courtesy of the Pittsburgh Cultural Trust.

Friday, September 27: Gallery Crawl in the Cultural District
5-10 p.m.
Turn over a new leaf in the Cultural District. The fall edition of the Gallery Crawl is bursting with all kinds of art. Pop into 30 Crawl stops at indoor and outdoor venues to experience public art, exhibition openings, U.S. premieres, international multimedia projects, live music, theater and dance performances, film screenings and more. Continue your artsy adventures at the Crawl After Dark events starting at 10 p.m.

Friday, September 27: World Square in Market Square
5-10 p.m.
Celebrate the finale of this new series showcasing international and immigrant communities. Enjoy live music by Hugo Cruz & the Caminos, Purple Lotus Guzheng and Timbeleza, see performances by Nandanik Dance Troupe and Pittsburgh Samba and shop for hand-crafted goods.

Friday, September 27: Factory Installed Open Reception at the Mattress Factory
6-8 p.m.
Be there when the Mattress Factory unveils new room-sized installations and large-scale multimedia projects during this free opening reception featuring nine acclaimed artists. The museum will also debut never-before-seen selections from its Greer Lankton Archive.

Mattress Factory

Laboratory for Other Worlds, Patte Loper. Photo courtesy of the Mattress Factory.

Friday, September 27: Pittsburgh Abides Garden Party at 25 Carrick Avenue
6-11 p.m.
Pay homage to all things Dude. This Big Lebowski-themed happy hour will feature a live film soundtrack by the Sweaty Already String Band, trivia contests, wacky games and more. Naturally, there will be White Russians, brews and burgers, and Dude merch.

Friday, September 27: An Evening with Lisa Congdon at the Ace Hotel
6:45-10 p.m.
Ready to embrace your artistic voice? Internationally acclaimed artist, author and educator Lisa Congdon will share candid insights about turning her artistic practice into a successful full-time career and will empower audiences to develop their own distinctive voice. Known for her colorful drawings and hand lettering, Congdon works for global clients including MoMA, Comme des Garçons, Facebook and many others.

Lisa Congdon

Lisa Congdon.

Friday, September 27: Governor’s Awards for the Arts at the August Wilson African American Cultural Center
7-8:30 p.m.
For the first time since 1997, the Governor’s Awards for the Arts will be hosted in Pittsburgh. Be there for the free celebration when Gov. Tom Wolf presents awards honoring the significant contributions of five outstanding Pennsylvania artists, arts organizations and cultural leaders. Don’t miss the Awards After-Party in the lobby and cafe featuring DJDBO, a cash bar and an iconic Pittsburgh cookie table.

Friday, September 27: Survival: After Hours at Carnegie Library of Pittsburgh
7-10 p.m.
Calling all citizens for an epic night of survival where you can support the library you love and channel your inner Katniss Everdeen. While Big Brother sleeps, “Hunger Games” fans can prepare for the apocalypse by mastering first aid skills, learning to preserve food and trying on outdoor gear. Participate in silk-screening and raft building activities, join a library scavenger hunt and much more.

Carnegie Library of Pittsburgh

Photo courtesy of Carnegie Library of Pittsburgh.

Friday, September 27: Jazz Poetry Festival at Alphabet City
7 p.m.
With a unique premiere every night, the dynamic Jazz Poetry Festival continues with The Possible 4. Performing new compositions featuring different combinations of musicians, the jazz ensemble will be joined by poets Margaret Ross, Christine Stroud and Kim Sousa.

Friday, September 27 through Sunday, September 29: Oktoberfest at Penn Brewery
Various times
Don’t miss Pittsburgh’s granddaddy of all Oktoberfest celebrations on the North Side. The Penn Oktoberfest brew will flow, along with the brewery’s complete lineup of classic German beers. Taste German culinary specialties like wursts, pretzels and roasted chickens and dance the night away to live oompah music.

Saturday, September 28: Tropical 5K Classic at Hartwood Acres
8 a.m.-12 p.m.
Fall may be here but the tropical fun awaits at this charity race. Crawl, climb and bounce your way through this Hawaiian-themed obstacle course to raise funds for blood cancer research and patient services. After competing, celebrate at a luau complete with Hawaiian refreshments, awards and steel drum music.

ASCEND Pittsburgh

Photo courtesy of ASCEND Pittsburgh.

Saturday, September 28: Regional Climbing Competition at ASCEND Pittsburgh
9 a.m.-9 p.m.
Calling all climbers to ASCEND Pittsburgh’s South Side HQ. The state-of-the-art climbing gym is hosting the 5th biannual Steel Town Throw Down — a regional climbing competition showcasing the mad skills of adult and youth competitors from five different states.

September 28: RADical Day and Farewell Party at Contemporary Craft
10 a.m.- 5p.m.
Help Contemporary Craft bid a fond farewell to its long-time Strip District HQ before it moves to a fabulous new space in Lawrencville. Their last public event in the Produce Terminal is a free RADical Days celebration where you can add a message to the gallery walls, salvage objects in a garage sale, make woven paper coasters using postcards and more.

Saturday, September 28: Dollar Bank Junior Great Race at Point State Park
11 a.m.
Calling all runners 12 years old and younger to the annual Junior Great Race! The highly anticipated day of fun and fitness will also include a Family Fun Run, Tot Trot and Diaper Dash.​ Don’t miss the pre- and post-race activities in Point State Park.

Junior Great Race

Junior Great Race. Photo courtesy of P3R.

Saturday, September 28: Steel City Big Pour at Construction Junction
1-4 p.m. & 6-9 p.m.
Celebrate SeptemBEER at this long-time mecca for craft brews. Within Construction Junction’s sprawling warehouse, you can sample craft beer, cider and mead from 70 top purveyors, fuel up with fantastic food vendors, bid on handmade “kegerators” and more.

Saturday, September 28: Rivers of Steel’s Festival of Combustion at the Carrie Blast Furnaces
1-10 p.m.
The fun will sizzle, crackle and pop at this unique festival showcasing the creativity and innovation our region’s artists, makers and builders. Watch blacksmithing, welding and iron casting demonstrations, be dazzled by fire spinners and flame performers and join hands-on workshops. The fiery festivities will also feature live music, iron pours, a Second Shift Crafters market and more.

Festival of Combustion

Festival of Combustion. Photo by William C. Miller.

Saturday, September 28: Home Sweet Home at the Union Project
4-7 p.m.
What could be sweeter than buying homemade baked goods from local refugee communities? At Hello Neighbor’s inaugural fundraiser, you can support nonprofit’s vital work and taste delicious baked goods from Afghanistan, Bhutan, Democratic Republic of the Congo, Iraq, Myanmar and Syria made by refugee home chefs and local bakeries.

Hello Neighbor

Photo courtesy of Hello Neighbor.

Saturday, September 28: Hispanic Heritage Gala at the Westin Convention Center Hotel
6-11:30 p.m.
Celebrate National Hispanic Heritage Month at this gala benefitting the Pittsburgh Metropolitan Area Hispanic Chamber of Commerce Foundation Educational Fund. Hosted by Second Lady of PA Gisele Fetterman, the festivities will feature a presentation by keynote speaker Allen Gutierrez, a Latin inspired dinner, live Latin music, casino games and an extensive silent auction.

Saturday, September 28: Allentown Night Market along East Warrington Avenue
7-11 p.m.
See why Allentown rocks at this vibrant fall event featuring three artisan markets packed with eclectic independent businesses, wicked entertainment by Pittsburgh Circus Arts, Trundle Manor and Kabarett Vulgare Sideshow, pumpkin carving contests and lots more.

Saturday, September 28: Jazz Poetry Festival at Alphabet City
7 p.m.
The 15th Annual Jazz Poetry Festival will close out the month with a performance by the multinational jazz quartet, The Possible 4. Playing all new compositions, the musicians will perform alongside award-winning poets Ilya Kaminsky, Tarfia Faizullah, Franny Choi and Bewketu Seyoum.

Don Flemons

Don Flemons.

Saturday, September 28: Dom Flemons at Shady Side Academy Senior School
7:30 p.m
The Hillman Performing Arts Series kicks off its new season with a solo acoustic performance by Grammy Award-winning multi-instrumentalist Dom Flemons, co-founder of the Carolina Chocolate Drops. Dubbed “The American Songster” Flemons’ vast repertoire spans 100 years of American musical folklore.

Sunday, September 29: The Great Race
8 a.m.
Start your engines for the biggest 10K in Pennsylvania! The course begins in Frick Park at Beechwood Blvd. and finishes in Point State Park. A beloved Pittsburgh institution, The Great Race donates $1 from every registration to the Richard S. Caliguiri Amyloidosis Fund. The 43rd annual event also includes a 5K run/walk, a running clinic, the Great Race Expo and more. More than 12,000 participants from 30 states plus Canada and the U.K. are expected to take part.

The Great Race

The Great Race. Photo courtesy of P3R.

Sunday, September 29: Pittsburgh Latino Festival at 24th in the Strip District
11 a.m.-4 p.m.
The first annual Pittsburgh Latino Festival will fill 24th St. between Smallman and Penn with family-friendly festivities. Try cuisine from Colombia, Venezuela, Mexico, Argentina and more from 16 food trucks, shop for  everything from peppers and coffee, to desserts and clothing in the vendor market, enjoy music by DJ Sondido Azteca and more.

Sunday, September 29: Riverview Park Day on the North Side
11 a.m.
Friends of Riverview Park, the Northside Leadership Conference, and Pittsburgh Parks Conservancy are teaming up to host this day packed with free activities including guided hikes, bike tours, live music and food.

Sunday, September 29: Western PA Lamb Cook-off in the Strip District
2-6 p.m.
Back with expanded offerings and new open-air format in the Strip, the Western PA Lambfest will showcase an all-female chef team. Keyla Cook, Veda Sankaran, Leila Khalil and Itha Cao will combine the flavors from Brazilian, Indian, Mediterranean, and Chinese to highlight Elysian Fields Farm lamb and side dishes.

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