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

Things to Do in Pittsburgh in September

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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!


Allegheny Observatory

The Allegheny observatory may be small by some standards, but it has made big contributions to the field of astronomy since being founded in 1859 by a group of telescope enthusiasts.

Currently the observatory is on the search for extrasolar planets, something we can all say is pretty cool. On Friday nights in the summer months the observatory opens up for public tours that are well worth checking out!

After looking for alien life, head down to a North Side brewery for a drink!

Tour Wigle in the Strip District

Wigle Whiskey

Wigle Whiskey is perhaps Pittsburgh's biggest success story in the spirits business, and those who have tasted their creations do not need to be told why that is.

If you love Wigle as much as we do, taking a tour of their distillery in the Strip District on this Saturday is an absolute must.

If you want to make a day of it in the Strip District, grab a meal at Penn Ave Fish Company or grab a glass of wine at Pittsburgh Winery.

South Park

South Park

South Park in South Park Township is one of those places that has something for everyone.

This park has numerous picnic areas scattered about, a wave pool, activities for visitors of all ages, and many other unique attractions throughout its 2,000 acres. Get a group together, pack up a big lunch, and plan to spend the day enjoying one of the county's largest and most beautiful parks.

North Side Farmer's Market


Most farmer's markets in the Pittsburgh occur on week days at times when it is quite hard to venture out to experience them.

The North Side's farmer's market runs throughout the summer on Fridays, meaning you can make it over to this one to gather everything you need for the weekend. We love this one as it is always home to an abundance of vendors, several of which you cannot find at any other market in the city.

Want to grab a quick meal in the North Side on your way home? Check out El Burro or call ahead for Wilson's Bar-B-Q!

Gateway Clipper


When the temperature starts to cool off in mid-September, it is time to get out on the water. One tour that is unlike no other is the Gateway Clipper, and their hour-long sightseeing tours will give you an appreciation for the city the way it was meant to be experienced- by the river.

After taking a cruise on the Gateway Clipper, take the Duquesne Incline up to Grandview for the city views or head down to South Side for a meal at La Palapa or Thai Me Up or a coffee at Delaney's Coffee!

La Casa Narcisi Winery

Casa Narcisi Winery

If there is any winery featured within this guide that is meant to show up and stay for a while, it is La Casa Narcisi.

This one has put incredible time, effort, and money into building one of the most beautiful estates of any winery in the region, and their outdoor patios and concert venue areas are designed for you to come out, pick up a few bottles of wine, and relax the day away. Perfect for a Sunday!

Science Center 21+ Night

Pittsburgh's Science Center

Throughout the year, Pittsburgh's Science Center hosts a 21+ Night- an adults only event that takes on special themes ranging from robotics to the science of beer and more!

If you've always wanted to visit this one but were looking to enjoy it away from kids (or with a drink in hand), a visit to enjoy one of the monthly 21+ nights is an absolute must.

Kayaking on the Three Rivers

Kayak with Venture Outdoors

Venture Outdoors is the premier outdoor activity organization in Pittsburgh and operates numerous events and activities in the city to encourage you to get out and exercise.

One of our favorites is found along the banks of the North Shore River Trail by PNC Park- their kayak rentals! Pick up a rental on a beautiful Saturday to explore the rivers with you, a few friends, and a paddle.

After paddling on the rivers, walk over to Local Brewhouse or Beerhead Bar to grab a beer or two!

Beechwood Farms

Beechwood Farms

Beechwood Farms is a 100+ acre private nature reserve in Fox Chapel that is designed to let you experience the serenity of nature. The numerous hiking trails wind their way through various habitats and lookouts, and there are always great options for bird watching and wildlife spotting here!

Wigle Barrel House

Wigle Whiskey Barrel House

Just because late September means the long summer days are coming to an end, doesn't mean that all the fun has to stop, too!

Wigle's Barrel House, located in the North Side, finishes up their year in early fall but still hosts a number of weekly events, live music performances, and more amidst the perfect ambiance- aging whiskey barrels!

Looking for more in the North Side? If it is not too late drive over to Allegheny Commons for Gus & Yia Yia's shaved ice (seasonal).

Oktoberfest at Penn Brewery

Oktoberfest at Penn Brewery

One fall event that we absolutely love is Oktoberfest, the annual Bavarian festival that has taken the world by storm for its celebration of all things beer.

In Pittsburgh there is no bigger Oktoberfest than at Penn Brewery, the city's oldest craft brewery.

Get here early as they fill up fast!

Klavon's Ice Cream

Klavons Ice Cream Parlor

Old time ice cream parlors seem to be few and far between these days, but if any in Pittsburgh are worthy of such a throwback, it would be Klavon's Ice Cream in the Strip District.

Head down to this one of their dozen indulgent sundaes or an old-fashioned ice cream soda to finish out your weekend!

Looking for more in the Strip District? Grab a meal at Smallman Galley or a coffee at Prestogeorge.

Insurrection AleWorks

Insurrection Aleworks

If you're driving through Heidelberg, located just south of the city, and are not paying attention you may not notice Insurrection AleWorks at all.

This small brewery is a local favorite with several unique beers on tap (try the Pink Yoga Pants if it is available- a pink sea salt and coriander gose) and a solid food menu including wood-fire oven pizzas, wings, and a charcuterie selection that would put most restaurants to shame.

Apple Picking at Norman's Orchard

Norman's Orchard

Norman's Orchard in Tarentum is one of the city's premier apple picking spots and has many varieties of apples ready to be plucked during the fall.

But be warned, the secrets of Norman's is out and the crowds descend upon this one during prime apple season!

If you come back into town later in the day, grab a Pittsburgh craft beer at Strange Roots in Millvale, Dancing Gnome Brewery in Sharpsburg, or a glass of wine at Wooden Door Winery near New Kensington!

Chatham Village

Chatham Village

Out of all of the neighborhoods in Pittsburgh, the small enclave of Chatham Village on Mount Washington is one of the most beautiful.

This historical neighborhood features homes built in Georgian Colonial Revival style that are absolutely gorgeous. So when the leaves begin to change head up to this one for a quiet stroll around this stunning collection of houses!

If you're able to spend more time on Mount Washington, take a hike around Emerald View Park's trails or grab a meal at Shiloh Grill or the Uzbeki restaurant Kavsar!

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