“If you don’t play, you don’t stay!”

Cheerily announced by Randy Gilson as he hugged and took selfies with visitors, that’s the sovereign rule for experiencing Randyland, his wonderland home and garden in the resurgent Mexican War Streets district of Pittsburgh’s Northside.  

Amid toys and visual delights such as mural-splashed building sides, plastic flamingos and welcome signs in dozens of languages hand-painted by visitors, joy animates this free-admission folk art landmark.

In 1982, Randy founded the Old Allegheny Garden Society to return beauty to his then blighted community. Creating “pop-up nature reserves” of flower-filled whiskey barrels, his concepts of turning “waste into wonder” and “people projects by people” attracted a following. Over time, the Society has produced some 800 barrels, 50 vegetable gardens, eight parks, trees and more.

Randy, also welcoming guests as a waiter at the Westin Convention Center hotel, is emblematic of the attention-getters, past and present, who give Pittsburgh its resilient energy and unique visitor appeal.

The story continues throughout Western Pennsylvania, including the Frank Lloyd Wright country of the nearby Laurel Highlands and beyond.

Open Canvas

Art and culture remain integral to Pittsburgh’s ongoing turnaround from now distant Smoky City days. Post-industrial decline halved the population from its 700,000-citizen heyday, leaving behind a vast urban infrastructure ripe for artistic takeover.   

Randyland, about a mile from downtown, is one Northside treat for groups. Another nearby is the acclaimed Mattress Factory. Formerly a Stearns & Foster mattress warehouse, artist

Barbara Luderowski’s boundary-pushing center of installation art features provocative works along with flexible event spaces.

Housed in an industrial park by the Pittsburgh-to-D.C. bike trail in the Chateau district, Bicycle Heaven is the world’s largest bicycle museum and sales/repair shop. Founder Craig Morrow’s nearly 4,000-piece collection ranges from rare antiques to bicycles from Hollywood films. Amid bicycles, Beatles and Elvis memorabilia, bobbleheads and much more, the upstairs can accommodate events for up to 500 people.

Next door is Johnny Angel’s Ginchy Stuff & Music Museum. Lead singer of The Halos—founded in 1966 and still going strong—Angel is one “ginchy” (’50s slang for cool) dude often on hand to share stories amid his Doo Wop, soul, pop and rock memorabilia.

Staying on the North Shore, the Andy Warhol Museum features the definitive collection of the Pittsburgh-born Pop Artist’s works on seven floors and an underground area. Versatile function spaces for 20 to 300 people are complemented by gallery access, tours and activities such as making Warhol-style art or starring in a Warhol-esque “Screen Test.”

The Warhol is one of Pittsburgh’s four Carnegie Museums, along with the nearby river-facing Carnegie Science Center; the other two are in Oakland, Pa. Imagination also takes flight at the National Aviary, home to some 600 rare and exotic birds.

Crossing into downtown’s Central Business District, my first check-in was at the Kimpton Monaco Pittsburgh. Following the brand’s adaptive reuse model, this artful update of a 1903 Beaux-Arts building features 248 guest rooms, 13 suites and 11,300 square feet of meeting space.

With black steel columns and etched glasswork accentuating the industrial chic atmosphere, the 120-seat The Commoner restaurant commands the hotel’s cavernous basement. Raised in Pennsylvania’s Amish Country, Executive Chef Wyatt Lash delivers farm-fresh American fare, with whimsical cocktails from youthful lead bartender Alex Dando. Herbs and vegetables grow on the ninth-floor rooftop, adjacent to the outdoor Biergarten.

Art in Motion

Hats off to the engineers who conquered Pittsburgh’s mountain-bounded valleys and hills, creating a beguiling connective weave of tunnels, viaducts and, most famously, 446 bridges for the city’s 90 neighborhoods and districts.

Circling back to the North Shore, I passed by the event-capable Penn Brewery and H.J. Heinz plant smokestacks before ascending historic Troy Hill, where guided tours of Saint Anthony Cathedral reveal the world’s largest collection of public Christian relics outside of the Vatican.

Edging down Rialto Street’s 24 percent grade (Pittsburgh has some of the nation’s steepest streets) onto the landmark 31st Street Bridge, I wound into Polish Hill and Lower Lawrenceville, where Church Brew Works is the brewpub update of a 1902 church.