156 Things to Do in Pittsburgh to Stay Busy Every Month of the Year


Things to Do in Pittsburgh in May

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Our ultimate weekend guide contains 156 unique recommendations of things to do in Pittsburgh in order to help you explore the city every Friday, Saturday, and Sunday of the year (one for each day). With each recommendation, we've also hand selected nearby restaurants, bars, cafes, and shops you may wish to visit while you're in the neighborhood if you have more time!

As always, please keep in mind that our weekend recommendations may vary based on season and typical event schedules. Exact dates and operating hours should be confirmed prior to any visit.

For more information on all recommendations, click through to our full articles or the businesses' websites for more information!

Riverhounds Game

Riverhounds Stadium in Pittsburgh

As a sports-crazed city, Pittsburgh has just about everything for those looking to cheer on a local team.

Our resident soccer team is the Riverhounds, and their stadium is perfectly located in Station Square, just across from the city. Check out their schedule and visit for a Friday night game in May to cheer them on!

Want to explore before or after the game? Consider a ride on the Gateway Clipper or Monongahela Incline, or head down to La Palapa in South Side for some amazing Mexican tacos.

Sewickley Park

Sewickley Park

Have a furry friend? Sewickley Park is as much for humans as it is for their favorite pooches!

This 1,000+ acre forest includes many blazed trails where dogs are allowed to visit off-leash with their humans. The trails here are not well marked, so you may want to order a park map in advance (most trails seem to end up at a main path, however, so it is easy to navigate with some intuition).

After visiting Sewickley Park, grab a gluten-free beer at Auroch's or a Turkish pizza at Ephesus.

Point State Park

Point State Park at Sunset

Point State Park has numerous activities to partake in on a Sunday, be it just hanging out around the fountain watching the boats go by, exploring the remnants of the old forts, or taking a stroll on one of the river trails outlining downtown on both sides.

You can do a lot here, but we highly recommend taking the trail on the south side of the park and heading down to the Mon Wharf during this visit to check out one of the most architecturally interesting sides of downtown Pittsburgh that most seem to miss!

While exploring downtown, why not grab a drink at The Commoner or a bite to eat at tako!

Pirates Game

PNC Park - Pittsburgh, PA

Raise the Jolly Roger! Head down to PNC Park for a Friday night game in May to cheer on the Buccos.

May is the perfect time for a Friday night game as the weather is still mild, the crowd is ready to ring in the weekend, and, depending on the year, the Buccos still have a shot at a winning season.

While at PNC Park, be sure to grab a piece of NY pizza at Slice and a beer from Rivertowne Brewing!

Pittsburgh Botanic Gardens

Pittsburgh Botanic Gardens

When you think of botanical gardens in Pittsburgh, your first thought is likely about Phipps Conservatory in Oakland.

But did you know that the city is home to a second botanic gardens in Oakdale (near Robinson Township)? This 460-acre property is a lovely outdoor garden that is perfect for a Saturday afternoon stroll while the late spring flowers are still out.

After visiting Pittsburgh Botanic Gardens, make a reservation for an incredible (and fancy) dinner out at Hyeholde.

Randyland

Randyland

If you are feeling down about yet another Sunday in the Burgh, head to Randyland, a place that is aptly called Pittsburgh's most colorful spot.

This attraction is the brainchild of Randy, a local artisan who wanted to bring color and happiness to the North Side in the mid-90s when the neighborhood desperately needed it.

His project grew, and grew, and is now a neighborhood icon that you have to see to believe.

Want to spend more time in the Mexican War Streets? Head up the staircase on Arch Street for an amazing Pittsburgh view, or walk through the City of Asylum's art pieces on Sampsonia Way on your way to Commonplace Coffee!

South Side Bar Crawl

Are you 21 (or maybe 21 several times over) and looking for an epic bar crawl? Pittsburgh's South Side is calling for you.

With bars of all sizes, qualities, and offerings on just about every corner, this neighborhood is the perfect spot for those wanting a night out that lasts well into the following morning.

Looking for a few quick stops for food? Why not try the Pub Chip Shop, Fatheads, or, if you have a bit more time, Streets on Carson?

Raccoon State Park

Raccoon Creek State Park

Located about 30 minutes west of Pittsburgh, Raccoon Creek State Park is a 7,500-acre forest which includes a massive lake and even a wildflower reserve.

Add in the fact that there are over 40 miles of hiking trails and very few visitors, this is one spot where you can get out and experience nature almost entirely alone!

On your way back into Pittsburgh stop in Westwood/Greentree to visit Antney's for some delicious ice cream.

North Park

North Park Lake in Pittsburgh

It is rare for us to recommend two of the same kind of activities in any given weekend in this guide, but in early spring we can't help but want to be outside as much as possible.

If the weather is nice, head up to North Park on Sunday to take a long walk around the lake, or possibly head up into one of the main trails in the forest before having lunch at the OTB Bicycle Cafe along the shores of the lake.

Want a glass of wine after your hike? Drive over to Gibsonia to visit the impressive Casa Narcisi winery.

West End Lookout

West End Lookout

While Grandview Avenue is the most iconic place for skyline views in the city, the West End Lookout is perhaps the second most popular spot to see the city we all love.

This tiny park located in the West End is home to an incredible view of the city that is beautiful day or night (and is one of our preferred spots to check out the city's many fireworks shows!).

Kennywood

Kennywood

The end of May marks one very important date in Pittsburgh- opening day of Kennywood!

Head down to this one in the late spring before the crowds pickup and the lines get long. We can already smell the potato patch fries now.

If you leave Kennywood early, check out Brew Gentlemen in Braddock for of our favorite beer in the region, or head over to Blue Dust in Homestead for sandwiches with house-smoked meat.

St John's Cemetery Views

St. John's Cemetery Views

If the skyline views on Friday inspire you to find more, head over to Spring Garden on Sunday to check out an angle of the city you've likely never seen before- from St. John's Cemetery!

This spot is often considered to be one of the best kept secrets in the North Side, and although we are suggesting you should visit, keep in mind this is a cemetery and to be respectful at all times.

After checking out the view why not head over to Troy Hill for a meal at Scratch or visit Perry Hilltop for a hike around Riverview park?

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