Matthew Obernauer was 12 when his grandfather opened a built-in hallway cabinet in a New York City apartment and showed him an unopened bottle of H. Obernauer whiskey. The label dated to 1887, two years after Herman Obernauer founded his Pittsburgh business, according to the Pittsburgh Post-Gazette. The company stopped operating in 1915 at its storefront at Fifth Avenue and Stevenson Street in Uptown. Now Obernauer, Herman's great-great-grandson, is bringing the name back with a tasting room at 2613 Smallman Street. That building was Kingfly Spirits' home until this year.
A few blocks inbound, Isaly's is working toward its own return at 2111 Penn Avenue. The Strip's next arrivals are Pittsburgh names older than the Strip as most people know it, and they are moving onto blocks where businesses from the last decade have left or are on their way out.
Two Old Names, Two Rooms That Opened Up
The Kingfly building shows the pattern most clearly. Obernauer bought the Civil War-era former horse stables this spring after Kingfly closed. He told the Post-Gazette that what drew him was "its character as an older building that had been beautifully repurposed," and that "we had to move fast." The space is 6,000 square feet over two stories.
Isaly's tells the same story on Penn Avenue. In September, USA Today reported that Bass & Bennett Trading Co., a longtime furniture and home goods retailer on Penn, was preparing to close and discounting its remaining stock. The same piece noted that Isaly's was getting ready to open "just a few storefronts away."
Both comebacks are coming from a long way back. Isaly's says the Strip shop will be its first new store in decades. H. Obernauer has been gone for more than a century. Neither one has announced an opening day.
Isaly's at 2111 Penn: Hiring, but No Date Yet
The Isaly's store page describes a 3,500-square-foot shop with a deli counter, chipped chopped ham, homemade Isaly's bars, Skyscraper scoops, old-fashioned candy bars and breakfast all day. USA Today reported seating for 50 to 70 people. The Conroy family has owned the brand since 2015.
The original target was summer 2026. USA Today reported that the opening was delayed and that company officials had not announced a new date. On October 6, Patch reported that Isaly's was hiring for the Strip location, which usually means a store is getting close. In its October 12 update, The Pittsburgh Wire said the store page still read "Opening Soon" alongside "Arriving in 2026," with no confirmed day.
In the meantime, Patch reported a limited-time "Grandma Isaly's Pizza" at participating Caliente Pizza & Drafthouse locations. It has a Grandma-style crust, White American cheese, chipped chopped ham, Isaly's BBQ sauce, pickles, onions and cheddar. Call your nearest Caliente to make sure it's still on the menu before you go.
H. Obernauer at 2613 Smallman: Barrels Ready, Label Still in Design
The tasting room will pour three spirits: an American whiskey, a bourbon and a modern take on historic Pennsylvania rye. Herman Obernauer was a rectifier, which means he bought spirits from other distillers and blended them himself. The revived company works the same way. Other distillers make the spirits, and H. Obernauer blends and bottles them at its warehouse in Lawrenceville.
As of early August, the label was still being designed and nothing had been bottled. The barrels were ready, and the goal was 1,000 cases in the first year. Obernauer gave the Post-Gazette an open-ended timeline: "We're shooting for the fall, which I like to tell people ends on Dec. 20. So it could be later."
His plans also connect to a whiskey business that's already in the Strip. He named Wigle Whiskey among the craft distillers he hopes the tasting room will lead people to try.
| Business | Address | What it will be | Status as of late October 2026 |
|---|---|---|---|
| Isaly's | 2111 Penn Ave. | Deli, ice cream, all-day breakfast | Hiring; summer target missed; no opening day announced |
| H. Obernauer & Co. | 2613 Smallman St. | Whiskey tasting room in the former Kingfly building | Owner's target is "fall," possibly later |
| Social Status | 2623 Penn Ave. | Flagship location | Grand opening event advertised for Aug. 20, 2026 |
| Flo Yoga Studio | The Hive, 139 28th St. | Hot yoga, Pilates, sculpt classes | Strip location listed on its site |
What Penn Avenue Lost This Year
Bass & Bennett's announced closing would follow an earlier Penn Avenue loss this year. The Original Pittsburgh Winery at 2809 Penn Ave. closed for good on Aug. 15 after 15 years, and its last nights were live music shows. Co-owner Tim Gaber told NEXTpittsburgh that rising costs, fewer drinkers and thin support for local music all played a part. He also pointed to confusion over lanes and parking after the city's plan to take Penn Avenue down to one inbound lane.
That street plan is still in progress. The City's Penn Avenue rightsizing page describes a revised design with one inbound lane, an inbound bike lane, loading zones and two lanes of on-street parking. It says any parking changes are on hold until the Strip District Parking Study is done and won't happen before 2027. Strip District Neighbors' State of the Strip 2026 report says design continues through 2027, with construction targeted for 2028.
So Isaly's is opening a daytime deli and breakfast counter on a stretch of Penn whose layout won't be final for a couple of years.
Where the Past Year's Openings Landed
The same report counts 16 new Strip businesses from July 2025 through June 2026, up from 13 the year before. That's the most since 2022. The report calls many of them "experiential destinations" and names Archive, Tapville Social, Sea Monkey, 1930 Cigar Bar, Bub's Lounge and The Roaming Bean's first permanent location. National retail also arrived with Sephora and Design Within Reach.
Many of these openings landed on Smallman and Railroad, and many are evening spots:
- Railroad Street. Juniper Grill, Atria's and 1930 Cigar Bar held grand openings together, and WPXI reported all three open on April 3.
- Sea Monkey, 2305 Smallman St. A Mediterranean-Asian restaurant with a late-night lounge and Vieux Carré, a speakeasy inside that you book separately. Dinner runs Wednesday through Saturday, 5 to 10 p.m.
- Tapville Social, 1447 Smallman St. Has a patio, takes reservations and offers pickup.
H. Obernauer's tasting room will add to that Smallman cluster. Isaly's will open on Penn as a deli, breakfast and ice cream counter.
The Strip Between Now and Dec. 20
The Saturday Markets at the Terminal ran every Saturday from May through October, and the season's last market was scheduled for Oct. 31. Walnut Capital took over managing the Terminal effective May 15. As of late October, the Terminal's Happenings calendar showed weekly events into early November, including the Wednesday 6 p.m. Magic: The Gathering cube draft at Aslin Beer, with no holiday market listed. These dated events are on the calendar:
- Nov. 11 and Nov. 18, 6 p.m. Game of Thrones "Winter Is Coming" cocktail classes at Wigle Whiskey, 2401 Smallman St.
- Nov. 21. Light Up Night tree lighting Downtown at the City-County Building and along Grant Street, per the City of Pittsburgh.
- Nov. 27 to 29, and Dec. 5, 6, 12, 19 and 20. Santa at the Senator John Heinz History Center.
- Dec. 9 and Dec. 16, 6 p.m. Classic Christmas Movies cocktail classes at Wigle.
- Dec. 20. Obernauer's own outer limit for "fall." If his tasting room opens on time, it'll open in the last stretch of the holiday season.
Isaly's has kept its timeline to "Arriving in 2026," which gives it until Dec. 31. For updates, the official Retro Isaly's Store page is the place to check.
I keep up with turnover like this because the business mix on a block changes how buyers and sellers see it. If you're thinking about a condo, loft or townhome in or near the Strip and want to know how this year's openings and closings fit into pricing, Nate Nieland is happy to walk through it with you. Book an appointment and we'll go over the specific blocks you have in mind.
