October Events in Pittsburgh

Party in the Tropics: Oktoberfest

Friday, October 4 | 7-10PM | Phipps
Bring out your bier steins! Dust off those lederhosens! Get ready to “prost!” to a night of spirited revelry in Phipps tropical paradise.  Gather your friends and head to Phipps Conservatory and Botanical Gardens for a healthy dose of revelry and rejuvenation as their Tropical Forest Conservatory transforms into one of the city’s most unique nightspots. At this reoccurring party, you can make their paradise your own as you indulge in sweet and savory morsels, taste unique cocktails and seasonal beer selections, dance to the beats of a live DJ, and unwind amidst lush greenery and rushing waterfalls. You won’t find a venue like this anywhere else in the ‘Burgh!

Stroll the Strip

Saturday, October 5 | 1-9PM | Osteria 2350
Strip District Neighbors invites guests from all over the region to the Strip on Saturday, October 5th to taste, sip, and stroll their way through one of Pittsburgh’s most cherished neighborhoods. The event will feature live entertainment, food and drink samples, family-friendly activities, and signature After Parties.

Hartwood Fest

Saturday, October 12 | 5:30-10PM | Hartwood Acres
Head to Hartwood Acres for the 11th Annual Hartwood Fest, a night filled with food, friends, and fun! Hartwood Fest is the annual fall fundraiser to benefit the Hartwood Acres stables. All attendees must have a ticket.

Best Bites Pittsburgh Downtown Restaurant Crawl

Saturday, October 12 | 2-6PM | Downtown Pittsburgh
The Best Bites Pittsburgh Restaurant Crawl is your chance to sample some of Pittsburgh’s best restaurants in one delicious afternoon. Enjoy tastings of each restaurant’s signature dish – or Best Bite – at 20 locations, have fun exploring Downtown Pittsburgh’s exciting restaurant scene, sample specialty cocktails, craft beer and drink pairings along the way, then head back to the Renaissance Pittsburgh Hotel for the Best Bites Awards After-Party.

Threadbare Fall Fest

Saturday, October 12 | 11AM-3PM | Threadbare Cider
Head to Threadbare on Saturday, October 12th for our 2nd annual family- friendly Fall Festival. Pay as you go activities include a pumpkin patch, pumpkin decorating, pumpkin and apple pastry sales from Mezza Luna Cafe, and build your own caramel apples. There will be games for kids and cider for adults! Pre-registration includes a free sample of their Fall Spice Cider!

Made & Found Fall Market

Sunday, October 13 | 10AM-4PM | Ace Hotel
Made & Found returns to the Ace Hotel Pittsburgh with a fall market featuring 25+ of the rust belt’s best vintage shops, makers, and artists. Brunch, coffee, and cocktails will be available for purchase. Admission is FREE. This is a family friendly event – you can even bring your dog!

Taste of Lawrenceville: Harvest Fest

Sunday, October 13 | 12-5PM | Bay 41
Head to Bay41 for Taste of Lawrenceville: Harvest Fest – a celebration of all things Lawrenceville to celebrate the fall season! Tickets are free, just register via Eventbrite and pay for what you wish to try at each vendor booth. Don’t miss this fun event filled with breweries, restaurants, live music and more!

Pittsburgh Boutique Fall Crawl

Friday, October 18 & Saturday, October 19 | 10AM-8PM | Pittsburgh
It’s time to Crawl Into Fall with the first annual Boutique Crawl! Featuring Vintage Grace Boutique, Whiskey Moon Boutique, Posh Local, Lynn & Barrett, and Wallflower Vagabond! Invite your girlfriends for some shopping, drinks, and fun!

Boo & Brew Bash 2019

Saturday, October 19 | 6-11PM | Downtown Pittsburgh
Eat, Drink and be Scary! Calling all Make-A-Wish supporters 21 and over… tour some of Downtown Pittsburgh’s best bars at the 9th Annual Boo & Brew Bash on Saturday, October 19, 2019. This Halloween-themed bar crawl offers classic brews and signature cocktails from the participating venues, culminating in an official After Party featuring late-night bites.

2nd Annual Pittsburgh Monster Pumpkins Festival

Saturday, October 19 & Sunday, October 20 | 6PM | North Shore
At this event, the North Shore Riverwalk and Great Lawn will turn into a pumpkin patch of prodigious proportions—with fruits weighing from 1,000 to over 2,000 pounds! They’ll drop them, carve them and, in one of the most “pumpkin-sanity” activities ever…create the silliest seascape possible with “The Great Gourd Race”—humongous pumpkin boats paddling the Allegheny River…competing in Pittsburgh’s fruitiest regatta!


October 19 – 20 & October 26 – 27 | Pittsburgh Zoo
Creep on over to ZooBoo at the Pittsburgh Zoo & PPG Aquarium for a Zoo-wide Halloween party! Come dressed in your favorite costume for the all-new, not-so-scary Trick-Or-Treat Trail sponsored by Allegheny Health Network. Or head into the Pumpkin Patch Pavilion for the Monster Mash Dance Off. Rain or shine, it’s a ghoulishly good time! Plus, the animals will be celebrating with their own Halloween-themed treats too.

Pittsburgh Magazine’s Whiskey & Fine Spirits Festival

Wednesday, october 23 | 5-9PM | Rivers Casino
Pittsburgh Magazine’s 2019 Whiskey and Fine Spirits Festival is scheduled for Wednesday, October 23 at the Rivers Casino Event Center. The Grand Tasting will feature over 250 premium distilled spirits from around the world including whiskey, scotch, bourbon, tequila, gin, rum, vodka, cordials and handcrafted cocktails. Guests can converse with industry representatives, experience interactive spirit lounges and enjoy dinner at the Grandview Buffet inside the Rivers Casino.

Halloween Happenings

Friday, October 25 | 4-8PM | Phipps
Bring little ghouls and ghosts to the gardens for family-friendly Halloween fun!
When you feel a chill in the air and see pumpkins everywhere, you know it’s almost Halloween — and Phipps’ spook-tacular gardens are the perfect place for your family to celebrate! Little ghosts and goblins can come to the conservatory in costume for a day of festive activities, all free with regular admission. Guests will enjoy face painting, play special Halloween games, delight at carved pumpkins, pot their very own creepy plants, sink their teeth into delicious, healthy snacks and more.

Halloween Bar Crawl

Saturday, October 26 | 4PM-12AM | Pittsburgh
Don’t miss the biggest Halloween Event of the year! Tickets include 2 free drinks, drink specials at each bar, food specials, professional photographers, and more!

Nightmare on Carson Street

Saturday, October 26 | 2-10PM | Pittsburgh
Bust out your best costume and get ready for a spooktacular party like no other this season. The official Nightmare on Carson Street event celebrates the scariest time of the year with thousands of your closest friends on Saturday, October 26th! Are you READY for Pittsburgh’s LARGEST Halloween event!?

BBQ & Brews

Saturday, October 26 | 1-5PM | Bay 41
BBQ, beers & live music, is there any better way to warm up on a fall day? Head to Bay 41 for BBQ & Brews, a celebration of some of the city’s best barbecue and breweries. Your ticket includes one 5 oz sample from each vendor, and all drinks are pay-as-you-go. Still hungry? Grab some sides and dishes from the vendors to fill your belly. Grab a punch card as you enter to make sure you stop at every booth, and don’t forget to put in your vote for your favorite BBQ in various categories.

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