Summer Guide (Mid to Late Season) 2023: Festivals, Fairs, and Fun Activities

The vintage race cars come screaming along a curve on the road through Schenley Park's golf course.

The vintage race cars come screaming through a curve on the road through the Schenley Park golf course during a Pittsburgh Vintage Grand Prix race. (photo: Rick Handler)

Summertime is undoubtedly the fastest time of year. It goes by much faster than, say, January, February, and March. We are now in the back half of summer. The peaches are ripening nicely and the summer season is at it’s peak. Maybe you’ve been enjoying summer fun since the start, maybe you’ve been tied up with work and other activities. Well, either way, it’s time to squeeze every last bit of juice out of the summer season. Before we know it, pumpkin spice will soon be appearing everywhere. You may have your own list of summer faves. We have also put together a curated list of some of the Pittsburgh region’s longtime stalwart summer events, plus a few more unique events. We also live in a beautiful natural region and have included several picks in that realm too.

Our EC Summer Guide (Mid-to-Late Season) categories include four basic summer-fun groups: Festivals and Fairs, Outdoor Music and More, Active Outdoor Recreation … and that perennial favorite, Miscellaneous. You can also check the EC Summer Guide (Early-to-Mid Season), which includes several attractions that run all summer long. Now let’s get started.

Rick Handler (R.H.) also contributed to this Guide.


Picklesburgh—July 21 – 23. Boulevard of the Allies (Downtown)

What would Picklesburgh be without a pickle juice drinking contest. Whoever drinks their quart of juice the fastest is named the Mayor of Picklesburgh. (photo: Renee Rosensteel for the Pittsburgh Downtown Partnership)

What would Picklesburgh be without a pickle juice drinking contest? Whoever drinks their quart of juice the fastest is named the Mayor of Picklesburgh. (photo: Renee Rosensteel for the Pittsburgh Downtown Partnership)

Sauerkraut. Kimchi. Dill-flavored popcorn. Deep-fried pickles. Pickle cocktails! It’s Picklesburgh. The ninth-annual, three-day, free event is now holding court in a new location on Boulevard of the Allies. If you can’t find it, look for the giant inflatable Heinz pickle (this year there are now two huge pickle inflatables), which resembles the company’s famous pickle pin. The festival recalls the city’s pickling history, which dates back to the 1800s, while also looking forward to our revitalized riverfronts and internationally recognized food scene. Enjoy free samples from area farms and restaurants, all of them offering their own take on pickled foods, before making the pickling purchase that’s right for you. Other “pickled” merchandise includes balloons and books. Chefs demonstrate how to pickle and can, and local musicians provide a pleasant soundtrack to your culinary wanderings. There’s a Lil Gherkins Activity Area for children. And, yes, the pickle juice drinking contest returns. Picklesburgh was three-times voted the No. 1 Best Specialty Food Festival in America in a USA Today readers choice contest. The Pittsburgh Downtown Partnership organizes the event with the help of numerous sponsors including Kraft Heinz. Noon – 10 p.m. Friday and Saturday. Noon – 6 p.m. Sunday. Downtown. (C.M., R.H.)

Pittsburgh Vintage Grand Prix Race Weekend—July 22 -23. Schenley Park

Drivers will start their engines and fans will lower their tailgates for the Pittsburgh Vintage Grand Prix race weekend in Schenley Park. The event is one of America’s largest vintage race events. Saturday will see race qualifying heats with over 150 vintage racers, and Sunday is the main race day. Both days’ action goes from 8:30 a.m. to 5 p.m. Other highlights include car shows featuring international, Italian, and British cars, a vendors marketplace, vintage racer ride-along, and various food and beverage offerings, Ferrari is the Pittsburgh Vintage Grand Prix’s Marque of the Year 2023. The race will also be hosting the Shelby convention. Qualifying race heats are on Saturday and the featured race is on Sunday. Look for Vintage Grand Prix events throughout Pittsburgh in the run up to the race. Charities benefiting from race proceeds are Autism Pittsburgh and the Merakey Allegheny Valley School. $5 charitable contribution admission charge. (R.H.)

Two older vintage, open-wheel racers jockey for position.

Two older, vintage, open-wheel racers jockey for position. (Photo: Rick Handler)

BLOOMFIELD LITTLE ITALY DAYS—August 17 – 20, Bloomfield.  

Bring your main squeeze or just have a good time solo at Little Italy Days in Bloomfield.

Bring your main squeeze or just have a good time solo at Little Italy Days in Bloomfield.

Ah, Bloomfield. Only in Bloomfield does a summer festival begin with a free concert and a celebrity bocce tournament with local celebrities. This East End neighborhood is known for many things. Long ago, it was home to native people affiliated with the Lenni Lenape. Johnny Unitas played quarterback for the semipro Bloomfield Rams before his storied career in the NFL. In springtime, runners laboring through mile 22 of the Pittsburgh Marathon get an astounding energy blast when they find Bloomfield’s main street lined with screaming spectators and blazing rock bands. And in mid-August the blast is called Bloomfield Little Italy Days. Immigrants from Italy’s Abruzzo region began to arrive around 1900. Their descendants have given Bloomfield great Italian food markets, an active Catholic parish … and a locale that’s now blooming with modern art galleries, eateries of multiple ethnicities, and more. Musical acts at Little Italy Days include Italian singers, rock, oldies, and soul. There’s also accordionist Hank Edwardo; celebratory urban street life scenes; and bocce balls being bowled. And did we mention the food? There are numerous food booths on the Liberty Avenue promenade. 5 to 9 p.m. Aug. 17; noon to 9 p.m. Aug. 18 – 19; and noon to 5 p.m. Aug. 20. Along Liberty Ave. and elsewhere in Bloomfield. (M.V.)

THE ART FESTIVAL ON WALNUT STREET— August 26 – 27, Shadyside.

August is a great month for strolling the tree lined streets of Shadyside and enjoying the fine arts and crafts during the Art Festival on Walnut. (Photo: Rick Handler)

August is a great month for strolling the tree-lined streets of Shadyside and enjoying the fine arts and crafts during the Art Festival on Walnut Street. (Photo: Rick Handler)

“Hip”—as in “Get hip,” rather than “Get a hip replacement”—is one of the oldest American slang terms still in wide use, and Shadyside’s Walnut Street is perhaps the longest-running hip district in Pittsburgh. Incredibly, it gets even hipper during the Art Festival on Walnut Street in late August. The Festival is popular, in part, because there’s so much art. The Walnut biz district is closed to motor vehicles and packed with booths where artists and craft people display paintings, prints, ceramics, handmade jewelry, and so forth ad infinitum. In addition: Some Walnut Street merchants bring out selected goods for sidewalk sales. Exotic food vendors descend. Established restaurants, coffee shops, and night spots operate in peak mode. And, music being the food of love and other good things, musicians play on. Official hours for the art and craft booths are 10 a.m. – 5 p.m. August 26 and 27, but you can bet that on Saturday the 26th, merrymaking will continue into the night. Walnut St. between S. Aiken and Ivy Streets with further activities adjacent, Shadyside. (M.V.)

A FAIR IN THE PARK—September 8 -10, Mellon Park

Beautiful glass art are among the works that can be scene at The Fair in the Park.

The annual A Fair in the Park will happen again this year in Shadyside’s Mellon Park. Promoted as a contemporary fine crafts and arts show and sale, it includes art and craft demonstrations, performances, music, food, and children’s activities. The fair is presented by the Craftsmen’s Guild of Pittsburgh and Citiparks. Food trucks and local vendors will be on hand including Pitaland, PGH Crepes, The Pickled Chef, The Coop Chicken and Waffles, and Revival Chili. Fair hours are: Friday, 1 – 7 p.m.; Saturday, 10 a.m. – 7 p.m., Sunday, 10 a.m. – 5 p.m. Fifth and Shady Aves., Shadyside/Point Breeze/Squirrel Hill. (R.H.)

PITTSBURGH IRISH FESTIVAL—September 8 – 10. Carrie Blast Furnaces.

We Banjo 3 and performers from other groups jamming together at 2015 Pittsburgh Irish Festival. (photo: Rick Handler)

We Banjo 3 and performers from other groups jamming together at 2015 Pittsburgh Irish Festival. (photo: Rick Handler)

Two rules of Irishness: (1) You do not have to be Irish to enjoy Irish things. (2) You might be more Irish than you think. This year’s Pittsburgh Irish Festival is the city’s 32nd annual celebration of Celtic culture—and since scholars say the ancient Celts populated lands from Austria to Portugal, this takes in everybody from Sigmund Freud to Cristiano Ronaldo. They’d both have a blast at the Festival. Irish and Irish-ish musical acts perform constantly through the weekend. The entertainment lineup includes Gaelic Storm, Bastard Bearded Irishmen, Screaming Orphans, Cahal Dunne, and The Low Kings.  There’s sure to be at least three pipe bands (there is no such thing as too much bagpipes). In addition to music and dancing, the Pittsburgh Irish Festival has storytelling, arts and crafts, experts on Irish/Celtic culture and genealogy, etc., along with Irish foods, Irish whiskey, stout, and mead. The festival is Irishness writ as large as it can be writ. Come one, come all. 4 – 11 p.m. Friday; 11 a.m.-11 p.m. Saturday; 9 a.m.-5 p.m. Sunday. 801 Carrie Furnace Blvd., Rankin. (M.V.)      


ALLEGHENY COUNTY FREE CONCERTS—Friday & Sunday eves, South Park and Hartwood Acres Amphitheaters.

As we’ve said before, crowds don’t lie. When people start bringing their lawn chairs in broad daylight to stake out spots for evening outdoor concerts, it’s because the music is free and the music is good. Such is the case with the Allegheny County Summer Concert Series, staged summer-long at two locations: Friday evenings, 7:30 p.m. at South Park Amphitheater, and Sunday evenings, 7:30 p.m. at Hartwood Acres Park Amphitheater. The lineup for the second half of this summer includes big-name acts in several genres. South Park has the Dazz Band (July 21), Fastball (July 28), Edwin McCain and Bill Deasy (August 18), and Punchline (September 1). Highlights at Hartwood include, Fitz and the Tantrums (July 23), Pittsburgh Ballet Theatre (August 20), and John Scofield (August 27).  3700 Farmshow Dr., South Park Twp., and 4070 Middle Rd., Allison Park.

Closing the Allegheny County summer season is a special 5 p.m. concert at Hartwood Acres on September 3, the evening before Labor Day. The 23rd Annual Allegheny County Music Festival features Men Without Hats, The Re-52s, and the Affordable Floors. Allegheny County is asking a $20 per vehicle requested donation for this one which benefits the Allegheny County Music Fund. (R.H.)

Concerts and More in the Great Outdoors — Through September, Various locations.

During our more temperate summer months, there are many entertainment opportunities in parks, shopping districts, and outdoor music venues. Most are free, some are not. Here are several Pittsburgh-area organizations and links to their summer offerings:

Pittsburgh Citiparks – concerts, line dancing, movies, farmers’ markets, foot races.

Jams on Walnut – concerts on Walnut Street in Shadyside with food and drinks.

Market Square Night Market and Concert Series – music, crafts, art, food, drinks, vendors.

Squirrel Hill Night Markets – music, food trucks, art, crafts, activities.

SouthSide Works Music on the Mon – local and national performers.

Narcisi Winery – wine, music, food.

Vinoski Winery – wine, music, food.

Baja Bar & Grill – indoor/outdoor bands, food, drinks, and DJs.

Carnegie Museum of Art – Inside Out events with local artists and arts organizations, art-making, DJs, food trucks, local brews, and kid-friendly treats.

The Pavilion at Star Lake – national touring music acts and local openers. (R.H.)


Free Outdoor Movies    

The City of Pittsburgh is screening a free series of films officially called Dollar Bank Cinema in the Park. Upcoming films include Back to the Future, Batman, Sonic the Hedgehog, and The Super Mario Bros. Movie.

Meanwhile, Allegheny County offers movie viewing locations in several county parks. This summer the movies are mainly family-oriented, animated films like Disney’s Turning Red and Strange World. (R.H.)


Moraine State Park Regatta — August 5 – 6, Moraine State Park, South Shore.

Kayakers enjoying the Regatta at Lake Arthur.

Kayakers enjoying the Regatta at Lake Arthur.

Pittsburghers used to have two regattas to choose from during the first weekend in August. These past few years if you gotta regatta, you gotta head north to Moraine State Park. The Moraine State Park Regatta—without powerboat races, and featuring a wide range of participatory events—takes place in Moraine State Park. Lake Arthur is about six miles long and over a half-mile wide in places, with several coves branching off. It’s popular for sailing and paddling, two of the many activities in which the Regatta offers try-it and learn-it sessions. The Moraine Sailing Club takes visitors on sailboat and catamaran rides around the lake. Other groups lead hands-on (and in some cases, feet-on) intros to kayaking, standup paddleboarding, fishing and fly casting, archery, nature walks, and even yoga. There’s also children’s activities and a butterfly release. Spectator events include paddle sport races, a 5k race, and a classic car cruise. Fireworks top things off Saturday night at 9 p.m. 

All but a couple of attractions are free. And, while all the gear you’ll need is provided, the Regatta at Lake Arthur is also a fine time to bring your own kayaks, hiking shoes, or whatever and explore Moraine State Park. 8:30 a.m. – 10 p.m. Saturday, and 10 a.m. – 6 p.m. Sunday. Also Crescent Bay Marina at Moraine State Park offers various types of boat rentals. 225 Pleasant Valley Rd., Portersville. (M.V.)

PedalPGH (group bike rides, other activities)—August 27, South Side and beyond

PedalPGH has group rides for all ages, fitness levels, and senses of humor.

PedalPGH has group rides for all ages, fitness levels, and senses of humor. (Photo: Murphy Moschetta)

Pittsburgh, always likable, is growing ever more bikable. New bike lanes and trails keep being added, cyclists and motorists keep learning to coexist, and new riders are finding that hills aren’t a drawback; they’re fun. The nonprofit organization Bike Pittsburgh (stylized BikePGH) does a lot to move the evolution along—one part of which is putting on the big annual bike-a-palooza called PedalPGH. This is the day with mega-multiple group rides, from a 7-mile “local loop” to a 62-miler that goes all around the region. It’s the day when you see people on bikes freakin’ everywhere. PedalPGH is sponsored by UPMC Health Plan. This year marks the event’s 29th anniversary, and although biking at any time is free, registering officially for PedalPGH buys you a ton of perks. You’re in on the group ride of your choice, with “amazing snacks” at rest stops. There’s a t-shirt and merch; there’s a festival at the start/finish line. Above all, your fee helps BikePGH continue its work in bicycle advocacy and education. Registered riders can start at any point on their route. The start/finish line will soon be announced. (M.V.)


Carrie Furnaces, Amazing Former Industrial Site, Open for Tours.

At Carrie Furnaces, modern urban art may mingle with majestic remains of industrial history.

At Carrie Furnaces, modern urban art may mingle with majestic remains of industrial history.

Archaeologists are excited to find well-preserved ruins of former times. Pittsburgh has such a treasure in plain view. The Carrie Furnaces site—twin blast furnaces towering above the Monongahela River, with auxiliary structures close by—is rare on a global scale, and astounding to visit. Not many old industrial facilities stay intact when they close. These immense furnaces, which boiled iron ore down to molten iron for U.S. Steel’s Homestead Works for nearly a century, were judged too much trouble to demolish after shutting in 1978.  And the sheer size of all that is left testifies to the brute-force nature of Pittsburgh’s historic industry. Just random details, such as massive heat pipes held together by bolts as big as human heads, can trigger awestruck imaginings of what it was like to build the furnaces—and to work there. The Carrie Furnaces site is open for public tours May through October under management of the Rivers of Steel National Heritage Area. Advance reservations are required, so make them at the web link above. Carrie Furnace Boulevard, Rankin. (M.V.)

COTRAIC 44th ANNUAL POW WOW—Sept. 23 – 24, Council of Three Rivers American Indian Center. Dorseyville.

At summer’s end, in late September, comes the lovely time known as Indian Summer. And with it comes the spectacular Annual Pow Wow held by the Council of Three Rivers American Indian Center. The Council doesn’t represent a particular American Indian nation or tribal group; it’s a service and cultural organization for everyone in our region whose ancestors arrived in America long before any Europeans did. The Pow wow reflects this diversity and is open to everyone, period. Major attractions are the music and dancing, which begin with the “grand entry” of dancers, then continues through the day. There are drum contests and dance contests. Also on tap are traditional American foods, plus arts and crafts (with items such as handmade jewelry, clothing, and ceramics for sale), and children’s activities. Although most dancing is done by experts skilled in the authentic styles, there are dances which all guests are invited to join. And, as at any pow wow, just plain socializing is a big part of the experience. Noon to 9 p.m. Sept. 23 and noon to 7 p.m. Sept. 24. 120 Charles St., Dorseyville. (M.V.)

For more summer events and activities see the EC Summer Guide (Early-to-Mid Season).

Photos not credited are provided courtesy of the individual organizations.

Mike Vargo is a Pittsburgh-based writer who covers theater, art, and other topics for Entertainment Central.

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