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10 Things To Do in Pittsburgh in May 2026

Posted on April 29
Francesca Dabecco

Francesca Dabecco

screen printed art for May Day

Pullproof Studio’s Mayday! exhibit features work from the Pittsburgh Print Group. (Courtesy of Pullproof Studio)

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 May Day rally in Downtown on May 1. Or check out Polish Hill’s annual celebration 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 new Mayday! exhibit where you’ll find screen-printed artwork exploring different themes associated with the word "mayday." The gallery’s opening reception is during Unblurred’s first Friday art crawl on Penn Avenue.

view of Allegheny River from Allegheny RiverTrail Park

Look for more events at the park like skate night and RiverTrail RecDay. (Francesca Dabecco / City Cast Pittsburgh)

2. Eat Riverside at Food Truck Fridays

One of Pittsburgh’s best alfresco experiences is back at Allegheny RiverTrail Park in Aspinwall starting May 15. 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.

“Ghost Kingdom” by Claudia Martínez Garay at Carnegie International.

“Ghost Kingdom” by Claudia Martínez Garay at Carnegie International. (Courtesy of Carnegie Museum of Art)

3. Admire Art at Carnegie International

Did you know that Pittsburgh is home to the longest-running exhibition of international art in North America? Don’t miss the 59th Carnegie International, 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 “Barter in Pittsburgh,” where visitors can swap unique arts and crafts.

table of food at Con Alma

I’m still dreaming about the fried tofu and live jazz at Con Alma in Downtown. (Francesca Dabecco / City Cast Pittsburgh)

4. Dine Out During Vegan Restaurant Week

You don’t have to be vegan to enjoy a plant-packed meal. Order specials during Vegan Restaurant Week, 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 more spring food festivals.

vintage home items

Treasure hunt for your kitchen or closet at Boheme Shops in Lawrenceville. (Francesca Dabecco / City Cast Pittsburgh)

5. Find Gems on a Vintage Store Crawl

Celebrate Vintage Store Day on May 16 with deals and steals at more than 15 shops in Lawrenceville. There’s something for everyone, from stylish clothes to retro home decor. Be sure to stop in my favorite store, Boheme Shops; every corner is filled with a different small business selling handmade and secondhand goods.

tulips at Phipps Conservatory

Phipps Conservatory’s new flower show, Alice’s Adventures in Wonderland, opens May 16. (Francesca Dabecco / City Cast Pittsburgh)

6. Buy Plants at Phipps’ May Market

Got a green thumb? Find unique plants, gardening accessories, lawn decor and more at Phipps' 90th annual May Market, 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. Find more May markets here.

concert stage at Pittonkatonk

Pittonkatonk takes over the Vietnam Veterans Pavilion in Oakland’s Schenley Park. (Courtesy of Pittonkatonk)

7. Jam at Local Music Festivals

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

Millvale Music Festival 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.

Ceramics from local artist Reiko Yamamoto.

Ceramics from local artist Reiko Yamamoto. (Francesca Dabecco / City Cast Pittsburgh)

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

Celebrate all things clay with a pottery sale 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 recently-renovated class space.

Block party in Greenfield

Blooming Local Block Party at Greenhouse Co-op is free and family-friendly. (Courtesy of Alternate Histories)

9. Hang Out at a Neighborhood Block Party

Pittsburgh’s Greenfield neighborhood knows how to have some fun. Visit the Blooming Local Block Party 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 Greenhouse Co-op, a charming plant store and cidery, and Alternate Histories, a studio and shop with cool sci-fi-inspired art.

Chalk Fest on the North Shore

Chalk Fest includes interactive spots where kids can participate. (Courtesy of Riverlife)

10. Skip Through Riverlife’s Chalk Fest

The North Shore will soon be covered with color at Riverlife’s annual Chalk Fest, 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.

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