May Events in Pittsburgh

Pittsburgh Wine Festival 2019

Wednesday, May 1 | 5-9PM | Heinz Field
500+ wines and dozens of the finest winemakers on Earth, the Pittsburgh Wine Festival is truly a world-class wine tasting event. Explore the world of wine (comfortably from the banks of the North Shore) at the 17th Annual Pittsburgh Wine Festival – Wednesday, May 1st, 2019 at Heinz Field. The Grand Tasting is 7-9pm. The VIP Tasting, two additional hours, begins at 5pm.

Garfield Night Market

Friday, May 3 | 6-10PM | 113 N. Pacific Ave.
Food, crafts, and fun for families on N. Pacific Avenue! The Garfield Night Market has four goals: to foster Garfield’s entrepreneurs, to give families a place to spend a Friday night together, to highlight Garfield’s creativity and energy, and to increase Garfield’s visibility to the rest of Pittsburgh by building a bridge between Garfield and Penn Avenue Unblurred.

Pittsburgh Tacos & Margs Crawl

Saturday, May 4 | 4-10PM | Carson City Saloon
Cinco de Mayo weekend is bringing a tequila-inspired bar crawl to the best South Side bars. Lots of tacos & margs, plus check in at each stop with the app to win prizes!

The Pgh Flea

Sunday, May 5 | 11AM-4PM | 242 51st St.
The PGH Flea is a free, all ages, indoor flea market. You can find great gifts and cool stuff from local vendors: clothes, art, jewelry, records, oddities, vintage, pop culture, books, handmade….and lots more! Drinks will be available upstairs as well! And you can still get that sweet, sweet brunch downstairs.

2019 Northside Sandwich Sampler

Thursday, May 9 | 6-9PM | Priory Hotel
Pittsburgh’s Grand Hall at the Priory is delighted to host, for the fifth year, the North Side Sandwich Sampler on Thursday, May 9 from 6:00 p.m. – 9:00 p.m! This event features food stations with samples of the best sandwiches from the North Side’s best restaurants and dives! Your admission allows you to vote on the best, gets you access to the fabulous food, entertainment from the Red Beans and Rice Combo, and a complimentary beer ticket. Cash bar is available! Tickets are $35

ZooBrew: Spring Hops

Friday, May 10 | 6-9:30PM | Pittsburgh Zoo
Party animals of the human kind (who are 21+) are invited to enjoy 45+ craft beer samples and a variety of bites while strolling through three outdoor locations including the Village, the Garden Tent and PNC Pavilion! **New for this year, Designated Driver tickets will be available for a limited time, April 11-18.

Uncover Squirrel Hill Mother’s Day Wine Walk

Saturday, May 11 | 4-8PM | Forbes & Murray
Join Uncover Squirrel Hill for their Annual Mother’s Day Wine Walk: self-paced wine tasting experience. The Wine Walk will take place in the Squirrel Hill Business District located on Forbes and Murray Aves in the heart of Squirrel Hill. Enjoy approximately 15 different wines, food samples and exclusive discounts at participating host Merchants.

Millvale Music Festival

Saturday, May 11 | 10AM-11:59PM | Millvale
The Millvale Music Festival is back for its 3rd season! This free music event will support and showcase local musical acts of all genres while showcasing Millvale’s venues and businesses. There will be 24 venues and 200 acts to enjoy!

Big Free Yoga

Saturday, May 11 | 8-9:30AM | ASCEND
Each month, ASCEND hosts a large-scale, community yoga class in the main climbing area called Big Free Yoga (BFY). The energy is truly inspiring and there’s no better way to start your weekend! All you need to bring is a mat and a friend.

Pittsburgh Dog Mom’s Day

Saturday, May 11 | 12-4PM | Mellon Park
Celebrate the 6th Anniversary of Wear Wag Repeat on Dog Mom’s Day. All the Pittsburgh pups and their mamas are invited! This takes place in the area of Mellon Park between the playground and the baseball field, look for the picnic shelter : )
This free event will include 3 amazing art installation photo areas so you can fill your camera roll with the cutest photos of you and your pup. Professional photographers will also be on hand to capture the dog joy. They’ll have food trucks for people and pets and plenty of grassy spots to hang out or roll around.

Butler Street Wish Crawl

Saturday, May 11 | 1-6PM | Lawrenceville
Head to Lawrenceville on Saturday, May 11th to enjoy some tasty beers and support Make-A-Wish! Tickets are $30 and include 5 beer tickets, light appetizers and exclusive food specials.

Bigham Tavern Mother’s Day Brunch Buffet

Sunday, May 12 | 10AM-3PM | Bigham Tavern
The annual Mother’s Day brunch buffet includes a complimentary mimosa for all the moms! The buffet will be available from 10am-3pm with their regular menu becoming available at 2pm. The price of the buffet is $16.95 and kids eat at 1/2 price!

Workshop PGH Mothers Day DIY Party

Sunday, May 12 | 2-5PM | Ace Hotel
A fun day for Moms to hang out, for you to bring your Mom or just come have fun and make some fun things while you leave the kids, plant babies, fur kids/ pets at home. A fun day for Moms of all kinds! For the DIY activities you can make all items at your leisure over the event including your choice of 3 of 4 activities offered.

Neighborhood Flea

Sunday, May 12 | 10AM-3PM | 26th St. & Smallman St.
Shop, eat, workshop, treasure hunt, and grab delicious goodies to go! The Neighborhood Flea takes place at 26th and Railroad Streets in Pittsburgh’s Strip District. Parking at The Hub at 27th and Railroad is only $3 for Flea days!

Market Square Farmers Market Opening Day

Thursday, May 16 | 10AM-2PM | Market Square
Downtown’s showcase Farmers Market returns to celebrate another season with fresh produce and goods from local vendors! Enjoy a unique and convenient shopping experience that enlivens the city. The Market runs every Thursday from May 16 – October 31, 10:00 a.m. – 2:00 p.m.

Lawrenceville Art Crawl

Saturday, May 18 | 3PM-11:55PM | 4413 Butler St.
Produced by Redfishbowl, The Lawrenceville Art Crawl is designed to generate community-wide interest in local artists, musicians, performers, and small businesses. This free event lines Butler Street with unique performances & vibrant culture.

Lawrenceville Farmers Market Pre-Season Happy Hour

Thursday, May 23 | 5:30-7:30PM | 250 40th St.
It’s time to kick off another season of the Lawrenceville Farmers Market, but this year? There’s even MORE to celebrate. They’ve changed days (you can now shop on Tuesday evenings) and formed a new partnership with Pittsburgh’s largest market, the Bloomfield Saturday Market. They’ve also welcomed several new vendors to their already great lineup. More produce, more local eats, more baked goods, jams, jellies, and more. Come celebrate the start of the market season during this Pre-Season Happy Hour at Cinderlands Beer Co. in Lawrenceville. From 5:30-7:30 p.m., a portion of food and drink sales will benefit the market’s 2019 season.

Open Streets PGH

Saturday, May 25 | 9AM-1PM | East Liberty
Grab your walking shoes and come play on car-free streets of Homewood, Larimer, East Liberty, Shadyside, and North Point Breeze on Saturday, May 25th! Explore the longest OpenStreetsPGH route ever with 4.4 mile loop traveling through the East End. OpenStreetsPGH is a free, all-ages event that’s building healthier, more connected communities. OpenStreetsPGH invites the community to get outside and be active, providing an opportunity to reimagine our streets as places for people, not just cars.

Crawl of Thrones

Saturday, May 25 | 2-10PM | East Carson St.
Winter is coming to Southside Flats! Choose your house and pay the iron price in trivia for honorable prizes. The night is dark and full of terrors, but the wine and ale washes them all away!

Pittsburgh Water Lantern Festival

Saturday, May 25 | 5:30-10:30PM | Allegheny Commons Park
Water Lantern Festival is an amazing experience where you’ll witness the magic of the lanterns as they light up the water. Get your tickets at before they sell out!

Yoga in the Square

Sunday, May 26 | 10-11AM | Market Square
Pittsburgh’s favorite free yoga series is back for 2019 and bringing two free one-hour yoga classes to Market Square with some of the city’s best yoga instructors! Hosted by the Pittsburgh Downtown Partnership, Yoga in the Square occurs weekly on Sunday mornings and Wednesday evenings May 26 – September 29. Make sure you arrive early to secure your spot. Yoga in the Square is free, but be sure to BYOM (bring your own mat)!

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