Drinks Downtown & the Cultural District
The Speakeasy
A place for a drink in Downtown & the Cultural District, moderately priced ($$) and worth about an hour. Best time to go: After midnight.
Why go
Low-lit cocktail bar in the lower level of the William Penn, styled after the hotel's Prohibition years.
It is one of 7 curated places we feature in Downtown & the Cultural District, alongside 2 activities, 1 place to eat and 1 outdoor spot. 6 more of our picks sit within about half a mile in a straight line, so it pairs easily with Omni William Penn Hotel and Original Oyster House.
- Type
- Drinks · Nightlife
- Neighborhood
- Downtown
- Price
- $$
- Time needed
- 1 hr
- Best time
- After midnight
Nearby
The 6 closest curated picks in Downtown & the Cultural District, measured as straight-line distance.
- 1Omni William Penn Hotel
Grand 1916 hotel on Mellon Square, with a palm court lobby and a Prohibition-themed bar downstairs.
Stay · 0.0 mi straight-line - 2Original Oyster House
Pittsburgh's oldest bar and restaurant, open on Market Square since 1870, known for oversized fish sandwiches.
Food · 0.3 mi straight-line - 3Highmark First Night
Dec 31 arts festival across the Cultural District, with outdoor stages, a parade and an early fireworks show.
Activity · 0.3 mi straight-line - 4The Rink at PPG Place
Outdoor ice rink around a tall Christmas tree in the plaza of the glass PPG Place towers.
Activity · 0.4 mi straight-line - 5Future of Pittsburgh ball rise
At midnight the illuminated ball rises nearly 75 feet at Stanwix Street and Penn Avenue as fireworks go off.
Sight · 0.5 mi straight-line - 6Point State Park
Park at the tip of downtown where the Allegheny and Monongahela meet to form the Ohio.
Outdoors · 0.6 mi straight-line
On these curated routes
The Speakeasy is a stop on our Pittsburgh New Year's Eve route. Open it to see the full day-by-day plan.
When to go: weather by month, based on Mount Washington
Our climate figures for Downtown & the Cultural District come from nearby Mount Washington. Average daily highs in Mount Washington run from 34°F in January to 84°F in July; June is usually the wettest month. For The Speakeasy itself, we suggest: After midnight.
Modelled monthly averages for Mount Washington from NASA POWER, not a forecast. Mount Washington weather by month (covers Downtown & the Cultural District).
Getting there
Map links open a live search for The Speakeasy, so hours and directions come straight from the map app.
- Coordinates
- 40.44060, -79.99660
- Destination
- Downtown & the Cultural District, Pennsylvania
The Speakeasy: quick answers
How much time do you need at The Speakeasy?
Plan on about an hour at The Speakeasy. That is our curated estimate for a typical visit; groups that linger will want more.
When is the best time to visit The Speakeasy?
Our pick: After midnight. Insider tip: Stop in for a drink after midnight, away from the street crowds.
Which TripsCircle routes include The Speakeasy?
The Speakeasy appears on Pittsburgh New Year's Eve, a curated route you can open on TripsCircle and plan with your group.
Add The Speakeasy to your crew's plan
Save it to a shared TripsCircle itinerary, settle the timing with a quick poll, and split the costs with everyone going to Downtown & the Cultural District.
Plan Downtown & the Cultural District
Lists & regions
Curated recommendation, not live listing data. Confirm hours, prices, bookings and access before you go.