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City Cast Pittsburgh

Francesca Dabecco

It’s music festival season! Whether you’re into jazz, rock, punk, or folk, Pittsburgh has an event for you. Mark your calendar ⬇️

Groove to the sounds of brass bands and global street music at 

 in Schenley Park. This music fest has all of the best vibes of a community picnic or block party but with top notch tunes. It’s free and volunteer-run. Give a donation if you can!

Over 350 musical acts are set to perform across 32 stages at 

. The event is free and within a walkable .6 miles. Plus, there’s other entertainment like comedians and street performers. Check out acts at venues big and small, from Mr. Smalls to Grist House Brewery.

 with performances by six artists, food trucks, and vendors at 222 Ormsby Ave. in Mt. Oliver. All proceeds go toward the main event in September — a 

 dedicated to mental health and suicide prevention.

In addition to hundreds of arts and crafts vendors, you can enjoy live music at the 

 — now at a new location at Arts Landing in the Cultural District. At no charge, enjoy a mix of local and touring artist performances, from rock to alternative hip hop to pop-folk.

Pride Month just got even more fun! Shop from craft vendors and hear music from 

 at Allegheny City Brewing in East Allegheny. It will be a day of good vibes, fresh brews, and community camaraderie. All admission proceeds benefit Hugh Lane Wellness Foundation.

 at South Park Amphitheater and Hartwood Acres Park Amphitheater, from jazz and rock to soul and funk. The first concert is June 5 at South Park. Hear some tunes, and grab a drink from on-site food trucks like Black Dog Winery or Hop Farm Brewing Company.

 always includes cultural events, small business vendors, and performances celebrating the history and heritage of Black music in America. Mark your calendar to see 

 will rock out along the creek in Frick Park Hollow. Look forward to local artists, tasty food, environmental activities, guided walks, and more. The event, hosted by WQED icon Rick Sebak, celebrates Upstream Pittsburgh’s 25th anniversary. (Learn how Upstream takes care of our waterways and 

Grab your lawn chair! You’ll want to snag a spot in Schenley Plaza for WYEP’s Summer Music Festival. This free, outdoor concert is a fun day for the whole family. 

 of indie, pop rock, and alternative artists ready to jam out in Oakland.

From emerging local talent to regional headliners, the 

 brings together community and good tunes for a free, three-day celebration. Check out music, food, artists, and more in Pittsburgh’s historic East Allegheny neighborhood. Stay tuned for the lineup.

What’s better than enjoying a crisp beer and good music? 

 — a two-day event at Pittsburgh Brewing Co. in Creighton — will feature dozens of artists in genres like blues, rock, Americana, country, and jazz. It all benefits Autism Pittsburgh and Band Together Pittsburgh.

Forbes Avenue and Market Square will be filled with good vibes at 

. It’s less of a concert and more of a block party. Check out art, food, drink vendors, and music from legendary groups and up-and-coming artists.

The August Wilson African American Cultural Center brings world-renowned artists to Pittsburgh’s stage every year at the 

. The multi-day event is a great way to honor our city’s impressive 

 on June 23 at a fundraiser for the festival.

Punk returns to Pittsburgh! Four Chord Musical Festival will 

 on the South Side. The independent music fest — a haven for alternative, punk rock, and pop-punk fans — hasn’t been hosted in the city proper since 2019. The lineup drops today.

This charming South Pittsburgh borough knows how to throw a party. Get in a groove with live music across three stages, local food, unique vendors, a brew garden, and family-friendly 

It’s music festival season! Whether you’re into jazz, rock, punk, or folk, Pittsburgh has an event for you.

Your 2026 Summer Music Festival Lineup in Pittsburgh 

15 Pittsburgh Music Festivals for Good Tunes and Community

Find the best of everything that Pittsburgh has to offer.

Pittsburgh’s Best

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Live life in full bloom this month with vendor markets, live music, art shows, creative festivals, and more 🌼

1. Celebrate Workers’ Rights on May Day

May Day (May 1) is also known as International Workers Day, and our union town is a great place to celebrate. March in the 

 on May 2 featuring a costume parade, live music from the May Day Marching Band, and a potluck in West Penn Park.

Plus, Pullproof Studio in Garfield is showing a 

 where you’ll find screen-printed artwork exploring different themes associated with the word "mayday." The gallery’s opening reception is during 

One of Pittsburgh’s best alfresco experiences is back at Allegheny RiverTrail Park in Aspinwall 

. Grab beer from Trace Brewing and grub from a rotating lineup of food trucks to enjoy along the Allegheny River. It’s so peaceful and relaxing on the swings by the water, plus there’s a serene trail for walking or biking and a launch spot for kayaks.

Did you know that Pittsburgh is home to the longest-running exhibition of international art in North America? Don’t miss the 

, opening May 2 at the Carnegie Museum of Art. The exhibition features a wide range of art forms, like painting, photography, sculpture, video, and theater. Don’t stress — you’ll have the rest of the year to see it. But there are some fun opening events, like “

,” where visitors can swap unique arts and crafts.

You don’t have to be vegan to enjoy a plant-packed meal. Order specials during 

, May 11-17. Dig into sesame noodles at Con Alma, pineapple fried rice at Senyai Thai Kitchen, tofu chimichanga at El Sabor Latin Kitchen, and spaghetti and seitan balls at Spirit. Mark your calendar for 

Celebrate Vintage Store Day on May 16 with deals and steals at 

. There’s something for everyone, from stylish clothes to retro home decor. Be sure to stop in my favorite store, 

; every corner is filled with a different small business selling handmade and secondhand goods.

Got a green thumb? Find unique plants, gardening accessories, lawn decor and more at 

, May 8-9. (It’s a lovely Mother’s Day weekend outing.) Not a garden expert? That’s okay! Horticulturalists and sellers from local nurseries can give you tips — and there’s other fun items for sale like candles and jewelry. 

It’s music festival season! Groove to the sounds of brass bands and global street music at 

 in Schenley Park, May 8-9. It has all of the best vibes of a community picnic or block party but with top notch tunes. It’s free and volunteer-run.

 will fill the borough with beats on the following weekend, May 15-16. Over 350 musical acts are set to perform across 31 stages (indoor and outdoor) — all free and within a walkable .6 miles. Plus, there’s other entertainment like comedians and street performers.

8. Check Out Clay Art at Mother of All Pottery Sales

 at the Union Project in Highland Park on May 9. The market features more than 40 ceramic artists selling mugs, plates, bowls, vases, and more. It’s a good excuse to check out the church-turned-ceramics-studio and their 

9. Hang Out at a Neighborhood Block Party

Pittsburgh’s Greenfield neighborhood knows how to have some fun. Visit the 

 on May 16 for a local vendor market, live music, crafts led by Pittsburgh Center for Creative Reuse, and tacos from La Palapa food truck. It’s organized by 

, a charming plant store and cidery, and 

, a studio and shop with cool sci-fi-inspired art.

10. Skip Through Riverlife’s Chalk Fest

The North Shore will soon be covered with color at 

, a free two-day festival May 30-31. Take a stroll through Isabella Street and Allegheny Landing to see professional artists creating large-scale 3D chalk murals. It’s a great way to spend some time on the riverfront during Memorial Day weekend.

May in Pittsburgh: May Day celebrations, Pittonkatonk and Millvale Music Festival, Phipps’ May Market, Food Truck Fridays, Chalk Fest, and more.

The Best Pittsburgh Events in May 20206

10 Things To Do in Pittsburgh in May 2026

Many of Pittsburgh’s best food and craft markets are returning this month. Celebrate the season with vendors selling plants, vintage clothing, homemade wares, small-batch food, and more.

If you love Handmade Arcade’s annual holiday market at the Convention Center, check out their new springtime shopping event. 

 celebrates contemporary craft makers and artists from around the country. Browse over 100 vendors selling furniture, glass, basketry, ceramics, fiber arts, jewelry, metal, and more.

. Bring your own seeds, bulbs, plants, and pots to swap with neighbors at Velum Fermentation. Don’t have any? There will be plenty to purchase. Plus, you can check out other eco-minded vendors and workshops.

Step into an antique-lover's dream at the 

 at Heinz History Center. The fair features more than 50 local makers selling one-of-a-kind clothing, accessories, home decor, vinyl records, and more.

Any season can be spooky season if you want it to be! Head to Allegheny Commons Park (the section near the National Aviary) to shop for oddities, art, jewelry, and more at 

Construction Junction is a reuse superstore that sells all sorts of affordable items for construction projects — and they also hold 

. Swing by for retro toys, comics, books, vintage glassware, home goods, clothing, furniture, records, and more.

 and DIY workshops at two venues in Wilkinsburg. Check out vendors, a plant sale, and activities at their warehouse on Pennwood Avenue, then grab a free shuttle to the Wilkinsburg Train Station for a Sustainable Fair featuring repurposed goods, environmentally-friendly businesses, and more.

 with the City Cast Pittsburgh team at Southern Tier Brewing Co. on the North Shore. We’ll have a photo booth, live DJ, special beer on tap, and some very yinzer-ific vendors with a market hosted by 

They just don’t make ‘em like they used to. Shop from over 30 vintage curators and craft makers at the 

 at Velum Fermentation. Expect to find clothing, antiques, jewelry, and art — plus tiny tattoos and food and drinks.

 at Nova Place. There will be live music and trivia, games, local vendors, food trucks, and more — right near all of the football fun on the North Shore.

This little borough is packed with great businesses, and it's time to show them off! Head to 

 to find vendors set up all over the borough’s .5-mile shopping district: farmers, bakers, artists, crafters, and much more.

Shop from curated collections of plants, books, and locally-made crafts at 

 in Mellon Park in Shadyside. It’s the perfect way to get your garden started with native perennials, edible shrubs and trees, cooking herbs, and more.

After the plant sale, stop by the Pittsburgh Center for Arts & Media (also in Shadyside) for their 

 featuring glass works, woven bags, wooden cutting boards, art prints, ceramic items, and more. 

 food truck and Jackworth Ginger Beer will keep you refreshed with food and drinks.

Unblurred first Fridays just got even better! 

 is back on N. Pacific Avenue during the monthly art crawl in Bloomfield and Garfield. Shop for homemade goods, hear live music, and celebrate the creative energy in the neighborhood until the sun goes down.

Handmade soap, art prints, bespoke jewelry, sourdough bread, and locally-harvested honey — those are just a handful of things you can find at the 

. I’m a big fan of their sun catchers and Pittsburgh stickers.

Every Saturday through November, starting May 2

 is coming back to Liberty Avenue. Get everything you need for the week ahead, like locally-grown produce, coffee, meat, cheese, and more — plus lots of hot and cold food ready to eat. Don’t leave without a bouquet from Sol Patch Garden or treats from Jak’s Bakery.

. It’s a lovely Mother’s Day weekend outing. Not a garden expert? That’s okay! Horticulturalists and sellers from local nurseries are always so helpful and can give you tips — and there’s other fun items for sale like candles and jewelry.

 at the Union Project in Highland Park. The market features more than 40 ceramic artists selling mugs, plates, bowls, vases, and more. It’s a good excuse to check out the church-turned-ceramics-studio and their 

Head to SouthSide Works for the return of this popular 

. You’ll find local vendors selling food, vintage clothing, handmade goods, art prints, and more. It runs monthly on Sundays from May to October, with special events in Schenley Plaza. (Every time I’m there, I 

 is a must-visit this spring. Stop by Velem Fermentation on Sundays through September to shop for fresh-pressed juice, homemade pies, and handcrafted wares. It runs until 2 p.m., so go ahead and grab a beer while you’re there!

Sewickley’s Sweetwater Center for the Arts is celebrating its 50th anniversary, making it the perfect time to check out their 

 with artists, makers, food vendors, and more. Don’t leave without some delicious local treats and a bouquet of fresh flowers.

Celebrate Vintage Store Day with deals and steals at 

. There’s something for everyone, from stylish clothes to retro home decor. Visit my favorite store, Boheme Shops; every corner is filled with a different small business selling handmade and secondhand goods.

Shop from 30+ local vendors specializing in vintage clothing, hand-crafted goods, upcycled fashion, art, and artisan gifts at 

 at Spirit. They often have unique market additions like flash tattoos and photo booths. Tip: Swing around back for a slice from 

Enjoy food and music while you shop secondhand gems at the 

 in Troy Hill. Tip: Fuel your adventure with coffee and a breakfast sandwich from De Fer Coffee & Tea on Rialto Street.

Support women, nonbinary, and queer-owned businesses at 

 on the last Sunday of every month at Allegheny Commons on the North Side. The new, larger event space means there’s more room for vendors, a live DJ, food trucks, and coffee pop-ups.

Find vintage clothes and home decor, plants and seedlings, handmade goods, and more at these spring Pittsburgh pop-up markets.

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City Cast Pittsburgh Staff

Want to try some of the best bites and bevs in the Burgh? Save room for these spring food and drink events, from food truck festivals to taste test contests.

📍St. Nicholas Greek Orthodox Cathedral, Oakland

Celebrate this 64-year tradition with music, dancing, and of course, 

 like gyros, spanakopita, baklava, and moussaka. (

Stop into businesses along Forbes and Murray Avenues to try 15 different wines at this 

. You can stroll (and sip) at your own pace!

Join Humane Action Pennsylvania to explore our city’s 

. All week long, participating restaurants will offer discounts and specials. (I’m keeping my eyes peeled for what Chef Michael Godlewski is cooking up at 

, contestants compete to see who can make the best strawberry pretzel-inspired treat while raising money for a nonprofit of their choice. Tickets are $15 to taste test and vote on your favorites.

Enjoy brews and bites with proceeds benefiting nine parks through the Allegheny County Parks Foundation. There will be a kids fun zone, raffle baskets, live local music, and more at this 10th annual celebration. 

 while tasting specialty cheeses and desserts, browsing craft vendors, and grooving to live acoustic sets. The $27 ticket gets you a festival-branded glass and all the wine you can drink.

📍 Hollywood Casino at the Meadows, Washington

Head about 25 miles south of Pittsburgh to dig into grub from 

, take in live entertainment, cheers with craft beer and wine, and shop from regional artisans and vendors.

Celebrate craft and creativity at the first annual 

. It’s part culinary competition, part block party. Enjoy live music and get slices from Pittsburgh favorites like Badamo’s, Driftwood Oven, Spak, 77 Club, Slice on Broadway, Rockaway, and more.

📍 South Hills Village Mall, Bethel Park

Try gourmet dishes and sweet treats from 

, and shop from dozens of artisans showcasing handmade jewelry, art, and crafts. It’s free and family-friendly!

 with an iconic industrial backdrop. Live tunes, a roundup of food trucks, and arts and craft vendors will keep you busy while you tour the site. Not into drinking? Buy the cheaper designated driver ticket, and sip on nonalcoholic bevs.

Mark your calendar for Vegan Restaurant Week, Strawberry Pretzel Standoff, Pittsburgh Pizza Olympics, and more.

Pittsburgh’s Best Spring Food and Drink Festivals 2026

10 Food and Drink Festivals in Pittsburgh This Spring

The latest on the best and newest restaurants and bars in Pittsburgh. We'll help you find where to eat, drink, and socialize.

Pittsburgh Food & Drink

Food & Drink

Hundreds of thousands of people are headed for the Burgh to attend NFL Draft festivities, April 23-25. But the party isn’t just on the North Shore draft stage — there are celebrations all throughout the city!

All of that fun inspired local influencer and coder 

) where you can find events all in one place. 

 on the City Cast Pittsburgh podcast, then scroll for some draft weekend highlights ⬇️

. It’s your one-stop shop for check-ins, event schedules, maps, ticket management, transportation information, and accessing exclusive fan experiences.

Kick off festivities the day before the draft with a concert from hip-hop superstar Nelly at 

 — then return on the weekend for performances by ground-breaking EDM DJ Steve Aoki and Grammy-winning hip-hop artist 2 Chainz. The new outdoor entertainment space is right across from PNC Park and features a fast-casual restaurant, SugarBird, serving fried chicken, donuts, and soft serve ice cream.

Celebrate Pittsburgh’s culinary heritage and diversity with celebrity chef Andrew Zimmerman and more than 20 beloved local chefs at the Tower at PNC Plaza in Downtown. 

 tickets are pricey, but the proceeds help to bring healthy food to PA schools. Plus, word is that some Steelers and NFL Legends will be there!

Local businesses and restaurants are hosting local performers for 

. Kick it off with the grand reopening of Market Square and music by DJ Arie Cole, NASH.VILL, and Big Jus & Steeltown Horns. Then march through Downtown to enjoy R&B and funk at August Wilson Center and jazz at Con Alma. Or venture to other neighborhoods for indie punk at The Government Center, reggae at Club Cafe, and pop rock at City Winery.

The new four-acre civic space in the Cultural District will make its debut with a 

free party for Pitt fans and football lovers

. There will be food trucks, bars, a stage for live music, a gaming tent, vendors, and more — right along Fort Duquesne Boulevard with stunning views of the Allegheny River.

 all three days of the NFL Draft. Check out the 

, an immersive fan cave modeled after a 1970s Pittsburgh basement, photo opportunities with the Vince Lombardi Trophy, oversized replicas of the team’s six Super Bowl rings, and a custom art installation honoring the Terrible Towel.

Spread the love to small businesses! Head to the Pitt Building on Third Avenue to shop from some of Pittsburgh’s best Black artists and creators at a 

. It’s a collaboration between the Greenwood Plan and 

 will be spinning high-energy hip hop, R&B, and trap at Roxian Theater from 8 p.m. to 2 a.m. Come to dance with Arie Cole, DJ Shay, Solo Dolo, and Icy Pisces. The event is 21+, and a VIP package is available.

Take in the action with one of the best rooftop bar views in the city. 

 on the South Side will have a draft livestream, a special themed menu, and draft tracking sheets so you can follow along. Have a group? Reserve a table to get a complimentary bottle of a ready-to-drink cocktail and a commemorative event item.

Nothing says “iconic Pittsburgh" like a day in the Strip District. Close out NFL Draft festivities with 

. Shop local, grab a Parma Sausage sandwich, dig into a football-shaped pizza, cool off with Millie’s Ice Cream, sip on an East End Brewing beer, and more. Plus, if you spend $50 or more in the gift shop, love, Pittsburgh will buy you a drink!

On the last day of the draft, locals and visitors can run or walk through the North Shore and Downtown in a 

. The route will take racers across our iconic bridges and right into the heart of the action.

This is the easiest way to avoid traffic headaches and high parking costs. PRT is expanding service to include 

 all weekend with the $25 Draft Pass on the 

 If you must drive, know that several streets in Downtown and on the North Shore will be closed to vehicle traffic. There are 

Party for the NFL Draft in Pittsburgh with a music crawl, free fan festival in Point State Park, Slappers N Bangers dance party, Pitt Block Party at Arts Landing, and more.

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