10 Reasons to Visit Pittsburgh in May – Enjoy that Weather

Published by Jeremy. Last Updated on April 28, 2023.

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Pittsburgh in May is when we truly feel like it is spring. The frosts end, temperatures warm, and all we want to do is be outside as much as we can before the (sometimes oppressive) summer heat rolls in.

So for this one, we wanted to share several great activities that are coming up for the month that you can enjoy outdoors, as well as many festivals (often libation focused) that take place in May!

Pittsburgh Marathon

Looking down the Warhol Bridge

Fancy a long-distance run in Pittsburgh? Or maybe you want to cheer on those who are going for a new personal record? The acclaimed Pittsburgh Marathon is returning for another year on May 7th, 2023, and will take runners on a gorgeous run throughout the city (so watch out for street closures!).

In addition to the 26.2-mile marathon, this race also includes a half marathon, relay, and 5k- so all skill levels can find something to enjoy on race day!

Go for a Bike Ride

Ride a Bike on the Butler-Freeport Trail

Don't fancy yourself a runner? How about going on a bike ride around the city instead! There are many great Pittsburgh bike trails to enjoy including some of our personal favorites like the Great Allegheny Passage, the Butler-Freeport Community Trail, and if you're willing to drive a bit further, the Ghost Town Trail (our absolute favorite)!

You can even plan your outing to end around some breweries near bike trails. A post-ride beer never tasted so good, we're not going to lie.

Millvale Music Festival

Millvale Music Festival

The borough of Millvale, just north of Pittsburgh, is a hub for great restaurants, breweries, and seasonal events. Arguably, none is larger than the annual Millvale Music Festival, taking place on May 19th and 20th in 2023.

This festival features an array of acts at stages spread throughout the borough- some indoors, some outdoors, some at dedicated venues, and others at rather obscure places- like in the community garden (our favorite from a visit in 2022)!

Just be warned if you visit this one- parking can be a bit tight in the borough, so it is best to either Uber in or use one of the dedicated shuttles (if available) from nearby parking areas for the best experience.

Drone Skylight Show at PNC Park

Pirates Fireworks Nights are always a hit, but in recent years PNC Park has hosted a new kind of event in a similar style- a post-game drone show!

May 19th's show is poised to be a treat with music, art, and designs from the Marvel Universe being featured. So head to the ballpark for a game or pop over to the North Shore to check out this unique feature once the game wraps up!

Go on a Walking Tour of Pittsburgh

Pittsburgh Bridges

We love exploring Pittsburgh in May as the temperatures are rising, the flowers are blooming, and, when its not raining at least, the city is looking gorgeous.

So how about going on our five-mile self-guided walking tour of the city? This Pittsburgh walking tour hits the North Shore, Downtown, Mount Washington (with both Inclines), and more!

Hit the Road During OpenStreets

Open Streets with the West End Bridge

Whenever we travel, we love it when cities shut down main roads for pedestrian enjoyment be it walking, running, biking, and more. While Pittsburgh doesn't do this nearly as much as we would like, we do get three amazing events each year from the OpenStreets program, and the first returns in May!

May's route will take place on Sunday, May 28th and will connect the North Shore to South Side via Market Square, Forbes, the Armstrong Tunnel, the 10th Street Bridge, and East Carson Street!

In the past we've been able to bike through South Side, the Strip District, the West End, East Liberty, and more all without having to compete with traffic. So choose your preferred method of exploring and hit the open streets this May!


Looking for a fun event in the Strip District? One of our favorite restaurants, Kaya, hostes their annual street festival, aptly named KayaFest, with music, drinks, and a whole lot of delicious food on Sunday May 28th in 2023!

Pittsburgh Magazine's Wine & Spirits Festival

If you're sensing a theme that May's activities are all about enjoying some libations or getting out for some exercise, well, you're not wrong. Our last event to highlight for this month is Pittsburgh Magazine's Wine & Spirits Festival– a new event for 2023 taking place on May 20th at Rivers Casino!

We know that Pittsburgh Magazine always throws a great party (their Best Restaurant Party is always one of our favorites to attend each year) and we are excited to check out over 200 wine and spirit samples from vendors both local, domestic, and international! Going beyond tastings, there will be meet & greets with winemakers and distillers, bottle signings, and even an on-site popup store from Fine Wine & Good Spirits!

Sports in May

PNC Park Fireworks

The Pirates are back for another season at PNC Park with a number of great games in May. They take on the Blue Jays May 5th-7th, the Rockies May 8th-10th, the Diamondbacks on the 19th-21st, and the Rangers on the 22nd to 24th. Pick up tickets on Ticketmaster or Stubhub here!

The Riverhounds season is in full swing in May with two home games Highmark Stadium- May 13th against the Birmingham Legion FC and May 20th against the Las Vegas Lights FC. Pick up tickets on Ticketmaster or Stubhub.

Shows in May

Pittsburgh Symphony

Finally, there are a number of great shows in the Cultural District in downtown Pittsburgh in May. 

The Pittsburgh Symphony is having a Schooltime: Meet the Orchestra event from May 3rd to 10th, they are performing The Rite of Spring May 19th and 21st, and a unique take, Riot: Stravinsky's Rite of Spring in between on May 20th at Heinz Hall.

The PNC Broadway series is back in May with a limited run of Dear Evan Hansen from May 2nd to 7th, The Pittsburgh Ballet is performing The Sleeping Beauty at the Benedum Center from May 19th to 21st, and the Pittsburgh Opera is delighting with We Shall Not Be Moved on select dates from May 13th to 21st at the August Wilson Center to name a few!

Do you have a favorite Pittsburgh event in May to check out? Comment below to share!

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