Top 10 Places for Happy Hour Drinks in Shadyside

The Pittsburgh neighborhood of Shadyside is a great place to live, work, and play.

It boasts of some of the best shopping in the city-- as well as some of the best dining options. There is a cosy, neighborly feel-- and you can walk or take the the bus almost anywhere. Its centralized location has made it a great place to start a business as well. When the day of work-- or class-- is done, many people stick around to enjoy the lively happy hour scene in Shadyside. Whether you prefer a handcrafted cocktail-- or would rather have a local brew-- you are sure to find what you’re looking for at any of these top spots-- ready for your happy hour enjoyment.

The best kind of happy hour starts with a GiftYa electronic gift card. It’s the best way to start the evening off right-- especially if you were the recipient of such a thoughtful gift! They are accepted at all the Shadyside locations listed below-- as well as many more throughout Pittsburgh. Surprise your favorite Shadyside local with a gift to any of these fantastic happy hour locations below!

1. Tipsy Cow

A great place to grab happy hour drinks and bites


salad at the tipsy cow
Image courtesy of Tipsy Cow. This spot is a great place to slow down after a long work week.

5741 Ellsworth Ave.

Pittsburgh, PA 15232

412-404-8409

Mon-Fri 4pm-2am

Sat-Sun 11am-2am


The Tipsy Cow is one of the best places in Shadyside to grab a relaxing drink after work. They have daily specials in addition to their daily half off menu at happy hour.

Thursday nights the sangria is also half off! Make sure to check this place out the next time you’re craving a burger-- which the locals agree are delicious-- and a cold drink.

“Nice little hometown bar and restaurant..The beer selection is nice and the wait staff is always polite.” -Yelp Review

2. Shady Grove

A nice, low key place to do happy hour


shady grove
Image courtesy of Shady Grove. If you’re looking for a solid happy hour, look no further than Shady Grove.

5500 Walnut St.

Pittsburgh, PA 15232

412-697-0909

Mon-Sun 11am-2am


Shady Grove is a popular spot in Shadyside-- one that is right in the main business district-- which makes it easy to get to. They also offer daily specials-- in addition to their regular happy hour-- for those patrons who just need a place to unwind after work. If you’re up for it on the weekends-- they also offer a fantastic brunch!

“Shady Grove is always a good stop when in Shadyside. The food is excellent, the wait staff is fast and friendly, and the atmosphere is amazing.” -Yelp Review

3. Steel Cactus

A great option for margaritas at happy hour


steel cactus
Image courtesy of Steel Cactus. The margaritas are the popular drink with the locals at this Shadyside staple.

5505 Walnut St.

Pittsburgh, PA 15232

412-709-6444

Mon-Thurs 4pm-12am

Fri 11am-2pm

Sat 10am-2am

Sun 10am-12am


If you just can’t seem to get enough margaritas, then you’ll definitely want to check out the Steel Cactus. Although there are locations all across Pittsburgh, the Shadyside location remains one of the most popular spots.

You’ll find locals hanging out here any day of the week-- and with their specials it’s easy to see why. The $5 appetizers and $10 pitchers of margaritas-- in any flavor-- keep them coming back for more.

“I have been here twice with friends and family. Staff are always nice and work hard...Happy hour and daily specials are a fantastic deal! There are food and drink specials.” -Yelp Review

4. Stack’d Shadyside

Burgers and drinks at this spot make a perfect happy hour


stack'd shadyside
Image courtesy of Stack’d Shadyside. A burger and a beer are a great way to relax at happy hour.

728 Copeland St.

Pittsburgh, PA 15232

412-682-3354

Mon-Wed 4pm-12am

Thurs-Fri 4pm-1am

Sat 11am-1am

Sun 11am-12pm


If custom burgers and craft brews are more your happy hour style, think of stopping by Stack’d Shadyside over on Copeland St.

Here you can create your own burger-- with any toppings you’d like-- and wash it all down with any of their amazing local and craft beers on draft. Most people come to happy hour for drinks and some food-- but if you’d prefer it-- there is a nice selection of milkshakes (and boozy milkshakes!) that are also readily available.

Make sure to stay for the late night happy hour on Fridays!

“Stack'd burgers is an awesome place for a good burger. We went when apps were 50% off which is a nice surprise.” -Yelp Review

5. Muddy Waters Oyster Bar

Put a little New Orleans into your next happy hour


muddy waters oyster bar
Image courtesy of Muddy Waters Oyster Bar. Some of the best oysters and cocktails in Shadyside!

130 S. Highland Ave.

Pittsburgh, PA 15206

412-361-0555

Tues-Thurs 4:30pm-12am

Fri 4:30pm-1am

Sat 10:30am-1am

Sun 10:30am-11pm


If you’d prefer more seafood with your happy hour, consider checking out Muddy Waters Oyster Bar. Their oysters are said to be some of the best in Pittsburgh, and are on special for this spot’s happy hour every day.

There is also an additional happy hour available Saturday afternoon-- just in case you weren’t able to get your cajun food fix!

Great casual atmosphere mixed with sophisticated fare. They have great happy hour oysters...Drinks were good with a full bar and signature cocktails and dessert cocktails.” - Yelp Review

6. Whitfield

This spot is nestled into the Ace Hotel


whitfield sandwich and chips
Image courtesy of Whitfield. Make sure to check out this spot in the unique Ace Hotel.

120 S. Whitfield St.

Pittsburgh, PA 15206

412-626-3090

Mon-Thurs 7am-3pm, 5pm-10pm

Fri 7am-3pm, 5pm-12am

Sat 7am-2pm, 5pm-12am

Sun 7am-2pm, 5pm-10pm


For a more sophisticated-- but not too upscale-- happy hour experience check out the Whitfield. This spot is located in the trendy Ace Hotel, and has quickly become a favorite amongst the locals and tourists alike. Their happy hour menu includes a couple choices of delicious finger foods-- as well as specials on beer, wine, and house cocktails.

“The decor and ambience of this restaurant allow for an enjoyable experience, with high ceilings, lots of greenery, and plenty of natural light.” -Yelp Review

7. The Urban Tap

A great place to relax with friends for happy hour


taps at the urban tap
Image courtesy of the Urban Tap. When you mix great beer with great food-- you get a great happy hour.

216 S. Highland Ave.

Pittsburgh, PA 15206

412-404-7723

Mon-Thurs 11am-11pm

Fri-Sat 11am-12am

Sun 10am-11pm


The Urban Tap is one of the first gastropubs to appear in Pittsburgh-- and it continues to show why it’s still one of the best.

The beers are always rotating according to season-- so there’s always sure to be a great selection of local and craft beer. Their pub food is the perfect accompaniment to the beer as well-- traditional American food done with a little creative twist.

“This was my first time here at this lovely establishment.  I was greeted with a very welcoming staff and must say my experience from start to finish was fantastic.” -Yelp Review

8. William Penn Tavern

The perfect place to get a happy hour drink after a long day


william penn tavern mural
Image courtesy of William Penn Tavern. You’ll definitely find a draft beer you like at this local sports pub.

739 Bellefont St.

Pittsburgh, PA 15232

412-621-1000

Mon-Sat 11am-2am

Sun 12pm-2am


William Penn Tavern is Shadyside’s favorite sports bar-- and home to some of the best happy hour specials around. With a different beer on special each night-- and wings on special four nights a week-- you’ll find yourself wanting to stop by often. There is also some great pub food and plenty of TVs to catch the game on-- you’re sure to have a great time!

“If you want excellent wings and a nice friendly environment to hang out around the shadyside area come here, you won’t be disappointed.” -Yelp Review

9. Casbah

Check this place out for a unique happy hour experience


casbah
Image courtesy of Casbah. A bit of the Mediterranean right in the middle of Pittsburgh.

229 S. Highland Ave.

Pittsburgh, PA 15206

412-661-5656

Mon-Thurs 11:30am-2:30pm, 5pm-10pm

Fri 11:30am-2:30pm, 5pm-11pm

Sat 11am-2pm, 5pm-11pm

Sun 11am-2pm, 5pm-9pm


If you’re looking for a different type of vibe for happy hour, why not check out Casbah? The atmosphere here is very chill-- and all kinds of people find themselves drawn to its welcoming lounge.

There is even a year round garden patio-- which adds to the unique ambiance of this place. Pittsburghers know this is a great place to unwind and have a happy hour that moves at a slower pace.

“Casbah's food is fantastic! If you want fresh, Mediterranean flavors that are still innovative, this is the place you need to come.” -Yelp Review

10. Harris Grill

A tried and true favorite of Pittsburghers for happy hour


harris grill
Image courtesy of Harris Grill. The friendly staff here keeps customers coming back for more.

5747 Ellsworth Ave.

Pittsburgh, PA 15232

Mon-Sat 11:30am-12am

Sun 10am-12am


The Harris Grill in Shadyside is a favorite amongst the locals-- so much so that they opened two other locations in downtown and Mt. Washington. It’s easy to see why-- this spot offers a great place to slow down and take it easy at the end of the day.

There are always craft and local beers on tap, and their appetizers just hit the spot for happy hour. This place can get packed for happy hour-- which is due to the friendly nature of the staff and the welcoming atmosphere that this place exudes.

“Harris Grill is an awesome spot for a just beer or a full meal. I've been coming here for years and it never fails to provide a laugh or a delicious dish.” -Yelp Review

Everyone likes to relax and unwind after a long day of work. The Pittsburgh neighborhood of Shadyside offers some stellar options for doing just that. Stop into any of these spots after work and get your happy hour started right-- with a GiftYa personalized gift card! Do you have a favorite Shadyside spot for happy hour? Let us know what it is in the comments!






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