With a whiskey-making robot, a cat crawl and the chance to own a Keith Haring portrait made by Shepard Fairey, we’d say May definitely rocks.

Pittsburgh Wine Festival
Courtesy Pittsburgh Wine Festival.

1. Pittsburgh Wine Festival at Heinz Field: May 4

Move over Steelers, it’s time for the vintners to take over Heinz Field. Celebrating its 15th anniversary, the Pittsburgh Wine Festival is back with exciting changes and expanded programming. Amateur oenologists, sommeliers and viticulturists will be awed by the staggering variety of 530 wines from around the globe. Discover the age-old artistry of winemaking, sample top-of-the-line brands and enjoy delectable vino and food pairings. A who’s who of worldwide wine luminaries, this year’s roster features Château Montelena, Silver Oak and Heitz, along with industry standouts like Gaja, Antinori and Cakebread. Can’t tell a Beaujolais from a Tempranillo? No worries, because after a brief hiatus, the festival is reviving its lively “Taste Great Wines” seminars. Named one of the country’s Top 10 wine shows, the great grape gathering includes a VIP session from 5 to 7 p.m. and a main “Grand Tasting” event from 7 to 9 p.m. New to the event? Check out a festival guide to start planning your wine adventures now. Buy tickets.

Wigle Whiskey
Photo by John Tarasi, Wigle Whiskey.

2. Season Opening Party at Wigle Whiskey Barrelhouse & Garden: May 5

Robots can explore Mars, drive cars and even help fight cancer, but have you ever seen a robot that can make whiskey? Innovations in distilling and tech will make history, the barrels will roll and the malt will flow when Wigle unveils its new robotic assistant. Kicking off the season of al fresco libations and serving as a release party for its newest maltmalt whiskey, the Barrelhouse Opening & Release Party will feature Millieʼs Homemade Ice Cream milkshakes, live music by the Mixus Brothers, bites from Baby Loves Tacos and more from 6:30 to 9 p.m. Watch the bot demonstrate a traditional floor-malting process during tours, learn about Pittsburgh’s pre-Prohibition whiskeys and distillery owners, and sample the delicious new spirit. Developed in collaboration with Spoonwood Brewery, the distinctive release is distilled from four different malts, boasts a smoky characteristic and creamy mouthfeel, and sports a label designed by Jen Joyce. The malty mayhem begins at 5 p.m. with the not-to-miss “Barrel Roll,” featuring floats traveling from Wigleʼs Strip District distillery to its Spring Garden barrelhouse. Buy tickets.

Photo by Jae Roberto.

3. Pittonkatonk at the Vietnam Veteran’s Pavilion in Schenley Park: May 6, 1-11 p.m.

Seven touring bands, six events, eight school programs, and an infinite labor of love: Pittonkatonk is about much more than honking horns. Back with its biggest festival yet, this year’s brasstastic happening has something for everyone. The staunchly populist celebration kicks off May 5 with PRINTonkatonk at Artists Image Resource, where you can design your own posters and t-shirts and enjoy performances by May Day Marching Band. Pittonkatonk’s signature May Day Brass BBQ heats up May 6 with a free, all-ages potluck-style music festival. The roster of brass band luminaries features everyone from Providence’s What Cheer Brigade and Oakland-based La Misa Negra to the Motor City’s Detroit Party Marching Band. It’s an out in nature, energy-fueled, communal, dancing and stomping love-fest you have to experience to understand. Providing free music in public spaces, Pittonkatonk promotes community engagement, connects attendees with national and local musicians, and blurs boundaries between performers, spectators, entertainment and activism. Pittonkatonk also includes a “Music, Labor and Resistance” roundtable and “Pretonkatonk” dance parties at James Street Gastropub and Brillobox. Get involved by donating to the Indiegogo campaign or volunteering.

Food Truck-a-Palooza
Courtesy Food Truck-a-Palooza.

4. Food Truck-a-Palooza at the Pump House: May 6, 1-7 p.m.

Arrive with a huge appetite at this granddaddy of all food truck festivals. Boasting 30 regional trucks (and counting) on the mouth-watering mobile menu, this fun foodie affair has a taste for every palate— from spicy Indian entrees and trendy tacos to savory crepes. Back with even more meals on wheels for its third installment, Food Truck-a-Palooza will set up shop at the storied and scenic Pump House. A trailhead along the Great Allegheny Passage, the Waterfront landmark played a pivotal role during the 1892 Homestead Strike—one of the most significant events in American labor history. Open to all ages, the festival will also feature hands-on children’s activities, live music by Joel Lindsey, broadcasts by BOB FM 96.9 and a VIP session. Don’t leave without casting your “Pittsburgh’s Choice” vote for the event’s best food truck. Buy tickets.

Keith Haring
Portraits of Keith Haring by Shepard Fairey (L) and Herb Ritts (R).

5. Art for Change at Westin Convention Center: May 8, 6-11 p.m.

A silkscreened portrait of Keith Haring made by Shepard Fairey. A fantastical porcelain sculpture of a giant moose head. Paintings of Pittsburgh landmarks. If you think these objects are only bound for museum walls, think again. These are just a few of the 200 outstanding works of art you can bid on for a worthy cause at PERSAD Center’s 29th annual benefit bash and auction. Debuting at a new Downtown venue, the highly anticipated auction boasts everything from photography and furniture to jewelry and travel packages. Don’t be shy with those bids, because 100 percent of auction proceeds will support PERSAD’s Free Care Fund and counseling services for the LGBTQ community and people affected by HIV/AIDS. Bid on one-of-a-kind art during verbal and silent auctions—including arresting black-and-white work by famed fashion photographer Herb Ritts, vibrant painting by former Steeler Baron Batch and distinctive pottery by Edward Eberle. Make the rounds to gourmet dinner and dessert stations and learn about PERSAD’s vital work in the community. Buy tickets.

Jennifer BaronArts & Entertainment / Jobs Editor

Jennifer has worked at the Mattress Factory, Brooklyn Museum of Art and Dahesh Museum of Art and is co-author of Pittsburgh Signs Project: 250 Signs of Western Pennsylvania. She also is co-coordinator of Handmade Arcade. Musically, she is in a band called The Garment District and is a founding member of Brooklyn's The Ladybug Transistor.