LGBTQIA+ Long Weekend Itinerary

Experience the welcoming Pittsburgh at these LGBTQIA+ owned or affiliated stops

Pittsburgh's welcoming 90 neighborhoods are full of LGBTQIA+ hotspots, and it would take way more than a weekend to see them all. Use our three-day itinerary as your guide to everything from fitness and outdoor rec to restaurants and late night fun.

And here's the best part: ALL of the organizations listed are LGBTQIA+-owned or affiliated!

Thanks to our friends at QBurgh for helping us develop this itinerary in partnership with their great organization.

Day One: Flowers & Fitness

You'd think this itinerary begins with bacon and eggs, but we're going to make you earn them! Start your LGBTQIA+ itinerary with a workout class at Pittsburgh Fit, where the incredible meets you at your ability level for an unmatched gym workout in the East End.

Now that you've worked up an appetite, it's breakfast time at Square Cafe! The corned beef benedict and bananas foster waffles are crowd-pleasers, but their very vegan brussels sprout hash is what keeps me coming back. While you're there, be sure to say hi to Sheree, Square Cafe's owner who ensures their commitment to providing community and support to non-profits remains at the forefront of their mission.

Your afternoon takes you from the most tech-forward part of the city into possibly our most scenic. Explore Schenley Park and you'll forget you're in the city as 456 acres of trails and woodlands surround you accompanied by beautiful views of the Downtown skyline in the distance.

See that gigantic glass structure? That's Phipps Conservatory & Botanical Gardens, a 14-room glasshouse featuring 23 distinct gardens with ever-changing seasonal flower shows. If you've worked up an appetite on your afternoon trek, grab something from Schenley Park Cafe and have your own picnic overlooking the city.

Finish your afternoon and treat yourself as you shop along Lincoln Avenue in Bellevue – named as one of the top 10 charming main streets in US. P Square Scents should be a must on this shopping spree; you can walk in any time and make your own candles and other custom-scented products.

That was a full day of experiencing Pittsburgh. Now, it's time to party. Start with dinner and drinks at Harold’s Haunt, Pittsburgh’s very own THEY-bar. Tell ‘em QBurgh sent ya as you fill up on their fun menu of Power-Ups, Potions and Elixirs with events like watch parties, trivia or open mics happening almost every night.

Feeling good? Bring those good vibes to the party at Blue Moon, and say hey to Andy behind the bar. Named one of the best gay bars in the U.S. and renowned for their drag shows, Blue Moon has produced two winners of RuPaul’s Drag Race.

Day Two: Bike & Burn the Midnight Oil

We hope you got a good night's sleep, because today we're going hard from the morning until the wee hours of the next. Let's begin by getting active! Pedal with Flying Colors, an LGBTQIA+ Bicycling Group with rides throughout the year, or explore with Venture Outdoors, which hosts a variety of inclusive events like woman and genderqueer mountain biking, Pride hikes and much more!

Breakfast at Pigeon Bagels is your reward for sweatin' it out. Grab any of their delicious, kosher bagels and check their Insta story for the (mostly) vegan pastry and breads offered that day at their Squirrel Hill location.

What sort of itinerary would this be without a stop at The Andy Warhol Museum? You'll traverse seven floors of the largest collection of Warhol art and archives in the world in his birthplace of Pittsburgh!

In the afternoon, explore Lawrenceville, one of Pittsburgh's trendiest neighborhoods with a chic coffee shop, boutique shopping, vintage finds, delicious food and buzzworthy breweries every step of the way. Make sure your shopping spree includes Trim Pittsburgh with a curated collection of menswear and unique brands you won't find anywhere else.

Take a nap if you need to, because tonight we're going out until the sun comes up. Start with before dinner drinks at Love, Katie Distilling, one of the newest distillers in Pittsburgh situated in a stunning black-and-white speakeasy where classic sitcoms play on the television as you sip seasonal cocktails. Grab a sandiwch from the Bridge City Brinery food truck (those pickle tots are an absolute must) and dessert Leona’s Ice Cream. They use real dairy that's 100% lactose free so anyone can enjoy!

Time to hit the party and the afterparty. We recommend starting old-school at Lucky’s with DJs, dancers and dancing on the second floor – note: cash only, smoking allowed. Marvel as Lucky's still stands with a changing Pittsburgh around it. (Need a smoke-free alternative? Check out P Town and the Baum Shelter instead)

Still going? We aren't stopping until you do. Finish your night at Hot Mass with an outstanding lineup of awesome local and visiting DJs every weekend, that goes well past 2 a.m.

Day Three: Live Like Royalty

Legs tired? Head aching? We've got the cure on day three of this itinerary. Start your final morning in Pittsburgh at the Ladies Who Drag Brunch at 5801 Video Lounge, a free drag show that includes new performers each week along with a rotating menu of fab food and cocktails.

Cap off your late start to the morning with some leisurely shopping in our Shadyside and East Liberty neighborhoods. Vintage clothing and accessories shop Eons Fashion Antique is a must-stop! This boutique is the go-to for costuming local Hollywood productions, and owner Richard is the Grand Marshal of the 2024 Pittsburgh Pride Parade.

Before we say goodbye, end on a high note with a Sunday Tea Dance with Kierra Darshell at Brewer’s, the oldest standing Gay Bar in Pittsburgh.

More to Explore: