It’s easy to get into a groove with your weekend plans — Friday happy hour at your favorite downtown spot, dinner at that cozy Italian restaurant you love, then wake up late for brunch at the place around the corner. But when you have family or friends in town or you’re just looking to try something new, it’s like you need to reinvent the weekend.

Instead of spending hours in a group text debating where to go for dinner or what to do with those days off work, consider this your Urbanist-approved guide for food, drinks and fun this holiday season.

Ace Hotel 

You likely knew this would be at the top of the list, but for good reason. Ace has it all when it comes to impressing out-of-towners: the brand recognition that shows off Pittsburgh’s cool factor, the ambiance that’s sure to elicit a few “Oohs” and “Ahhs“, and the multipurpose space that’s just as great for an early morning breakfast as it is for a late night game of tipsy ping pong (or even a mid-day coffee if all that exploring gets to be too much).

20/20 // @thecmoa x @studiomuseum should be mandatory for all PGHers

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The Carnegie Museum of Art 

You only have until the end of December to check out the renowned 20/20 exhibit at the CMOA, and you’ll definitely kick yourself if you miss this one. This collaboration with the Studio Museum in Harlem has been garnering praise from some of the biggest publications in the world, and its commentary on sociopolitical issues in America makes for an interesting afternoon that’s a whole lot more memorable than a trip to the movies. Finish up your gallery visit with a trip to the newly renovated Cafe Carnegie for a discussion over coffee or a glass of rosé.

Federal Galley

Is Smallman Galley your go-to spot to eat with a group? The chef incubator’s food hall style of dining makes it easy for everyone to find something they like, and Federal Galley, the brand new sister spot on the North Side, offers up the same perks in a totally different style of space. Head here for tacos, vegan sandwiches, deep dish pizza and more, all in a wide open room in the Nova Place building complete with the building’s original bank vault.


If you’re on the hunt for last-minute holiday gifts, skip the mall and head downtown to the Vignette pop-up shop. This collaborative shop features goods from Pittsburgh style heavy hitters Moop, Toll Gate Revival, Pavement and Vestis, so you’re sure to find lots of holiday gift ideas (or impress guests) with some of the best shops and makers that the city has to offer.  Hurry, they close their cute little doors this Friday.

The Schenley Park Skating Rink 

Want to go all out with the old-fashioned holiday fun? Then you have to go ice skating — and the rink at Schenley is just the spot. Sure, you could head downtown to the PPG Place rink, but there’s just something charming about skating outdoors while surrounded by the park’s snow-covered trees. Once you’re done, head over to the cafe at Phipps to warm up with a glass of wine or a local beer.

‘Tis the season… 🎄✨🥃

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Miracle on Market 

Get in the holiday spirit in a no-pressure setting by getting a little buzz on at this over-the-top holiday pop-up bar. This is Miracle on Market’s second year in Pittsburgh, and it promises the same crazy holiday decor, Santas slinging boozy shots and in-demand feel as last year’s pop-up. Get there early or be prepared to wait!

Snack Around

There are some many new spots to check out it’s hard to devote the time for full on dining (especially while impressing out of towners).  Our answer, a snack crawl.  This might be a progressive friend event with some additions/losses throughout the day or a dedicated group to make a good of it.  Here is where we’d hit.

x Morning: Bagels from Pigon  (housed at Work Shop in Garfield which is also cute) or donuts from Bitter Ends Lunchonette in Bloomfield.  Both have yummy coffee but if you are looking for an extra caffeine boost head to stand by favorites 4121.

x Lunch: Head to Ki Pollo for an empanada and maybe a single piece of their Korean fried chicken.  But remember, it’s a snack tour so don’t fill up! If you are looking for something a little lighter, grab a salad or smoothie from Reed & Co and stroll the streets of Lawrenceville.

x Snack: Merchant Oyster for a cup of chowder and a beer.  Now I know its crazy to think that chowder could be a snack but after you have had the light variety of chowders here you will understand.  If another beer is in order head down the street to the newly opened Cinderlands Beer Co.

x Dinner: We’d start with a cocktail at Fl. 2 and then head over Or, The Whale for bar snacks like radish with whipped foie gras butter and wood-fired octopus with chimichurri.  Sweet tooth?  Head to Millie’s off of Market Square for a hot chocolate or an ice cream.

x Cocktails: After fancying it up, head back up Penn for a perfectly lovely $7 classic cocktail at Tina’s.  And if you still are snacking, grab a popcorn.  And maybe continue on to Apetka for one more cocktail…it is the holidays after all.