Concierge

10 Things to Do in Pittsburgh This Week · October 15–18, 2026

Top Picks This Week

★ Coffee & Chocolate Festival

A festival of coffee and chocolate tastings and treats at the Monroeville Convention Center.

Saturday, October 17, 2026 · Monroeville Convention Center, Monroeville

★ Oakmont Fall Festival

A fall festival along Allegheny River Boulevard in Oakmont.

Saturday, October 17, 2026 · Allegheny River Boulevard, Oakmont

★ Chris Botti at City Winery

Jazz trumpeter Chris Botti plays early and late shows at City Winery's seated Strip District venue, with dinner service available.

Monday, October 19 & Tuesday, October 20, 2026 Early and Late Shows · City Winery Pittsburgh, Strip District

Music & Nightlife

Women Who Rock Benefit Concert Starring Taylor Dayne

A benefit concert for Magee-Womens Research Institute featuring Taylor Dayne, with special guests DJ Coachelly, Malina Moye & The Vindys, presented by Gibson Gives.

Saturday, October 17, 2026 6:30 PM doors · Stage AE, Pittsburgh

PromoWest – Stage AE

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Chris Botti at City Winery

Jazz trumpeter Chris Botti plays early and late shows at City Winery's seated Strip District venue, with dinner service available.

Monday, October 19 & Tuesday, October 20, 2026 Early and Late Shows · City Winery Pittsburgh, Strip District

City Winery Pittsburgh

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TJC Halloween Fest II

A Halloween show with live performances by a lineup of Pittsburgh-area artists at The Forge Urban Winery.

Saturday, October 24, 2026 · The Forge Urban Winery

@pgh.events

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Lawrenceville Halloween Bar Crawl

The 2026 PGH Social Club Halloween bar crawl through Lawrenceville, with 10 bars, drink deals, and costumes.

Saturday, October 24, 2026 Check-in 3:00 - 5:00pm; crawl 5:00 - 10:00pm · Lawrenceville

@pghsocialclub

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Date Night

Longturn Season Finale on the Finch Rooftop

The final open-air rooftop party of the season marks Longturn's 9-year anniversary, with fire performers and skyline views over downtown Pittsburgh; costumes or skeleton-themed attire encouraged.

Sunday, October 25, 2026 · Finch rooftop (@finchpgh), Pittsburgh

@longturnmusic

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Arts & Culture

Romantic Rachmaninoff

A Pittsburgh Symphony Orchestra concert at Heinz Hall celebrating Rachmaninoff.

Friday, October 16 - Sunday, October 18, 2026 · Heinz Hall, Pittsburgh

Pittsburgh Cultural District – Trust Arts Calendar

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Family-Friendly

Ringling Bros. and Barnum & Bailey Circus

The Ringling Bros. and Barnum & Bailey Circus takes over PPG Paints Arena for a multi-day run.