How to Spend 24 hours in this Western Pennsylvania Hallmark Town this Season
This little city in Pennsylvania’s Laurel Highlands is packed with charm, and what it lacks in size, it makes up for 10 times over in fun things to do! So if you’re looking to plan a winter trip to Greensburg, Pennsylvania, that’s filled with art, the great outdoors, and delicious food (paired with local craft beer, of course), you’re in the right place. Read on for our roundup of fun things to do on your next Greensburg getaway.
We’ve visited the Laurel Highlands on several occasions over the last few years and have fallen more in love with the area each time. Our most recent trip was hosted by Go Laurel Highlands, and we explored alongside some of our fellow content creator friends.
We also got some local, insider insights from two of them. Our friends Sarah, of @SarahLovesYinz, and Kim, of @KimHikedIt, are sharing their recommendations for exploring some family-friendly spots to round out the list below, so keep reading. But first…
Getting to & Around Greensburg, PA
Nestled in Pennsylvania’s Allegheny Mountains, and serving as the county seat for Westmoreland, Greensburg is less than an hour’s drive from Pittsburgh, PA, and just over three hours from both Washington, DC, and Baltimore, MD. There is also an AMTRAK station right in town, making it easily accessible from any of these cities and so many others across the Mid-Atlantic!
Warm up with Coffee + Waffles at Sundawg Cafe
As soon as you get into town, pop into Sun Dawg Cafe and sit down for some coffee, or chai tea in Seth’s case, and breakfast to fuel your day. We had the most festive holiday waffles, complete with whipped cream and red and green sprinkles on top. Like, c’mon, how cute is that presentation?
With breakfast all day, as well as more lunch-oriented items and a full bar, this cafe isn’t just a morning stop. We were so tempted to come back in for a late lunch and one of their delicious cocktails that we had heard so much about.
Take a Stroll Around Town
Now that you’re awake, get your footing and familiarize yourself with the area by taking a stroll around town. One of our favorite ways to explore new places is by taking ourselves on a little art walk, and if you’re like us, you won’t want to miss Art in the Alley. The town’s courthouse is also a sight to be seen! A trip around the nearby Saint Claire park is also worth a visit if you’re looking for some time among the trees right inside the little city.
Immerse yourself in Wintery Art Scenes at The Westmoreland Museum of American Art
This museum is free to visit and boasts several immersive installations and exhibits. Their Winter Tales immersive installation, which is on through January, transports you into winter scenes from their collection that have been animated and brought to life through 2700 projection, wintery effects, and surreal, dreamy surround sound. Artists featured include William Coventry Wall, Charles W. (Bud) Gibbons, Henry Koerner, and Ron Donoughe, and you can see some of their original winter works throughout the museum as well.
The museum prioritizes collecting works from underrepresented artists, and has deemed 2025 The Year of Women Artists. We particularly loved the Brynn Hurlstone: Resonance installation, which is an interactive piece that illustrates the pervasive, and often unseen, issue of domestic violence. We thoroughly enjoyed the Fountain of Forms gallery (pictured above), highlighting works by women sculptors as well.
Enjoy Lunch at J. Corks
When lunchtime rolled around, we walked a few blocks over to J. Corks. This Greensburg staple serves a variety of high-end American fare, and their beautiful dining room, complete with a cozy fireplace, was the perfect spot for our group. We’re looking forward to visiting in warmer weather, so we can experience their patio seating and sample even more things from their impressive (and extensive) menu.
Our server recommended the calamari, which was dressed with a sweet and spicy Thai chili sauce, and the truffle fries; both were 10/10. We then went on to enjoy a grilled chicken, beet, and goat cheese salad as well as a mushroom and swiss burger that was cooked perfectly. Everything was so good, but we were too stuffed for dessert, so we’ll need to fix that next time around as well.
Check Into The Grandeur Estate
The Grandeur Estate is without a doubt the town’s most elevated luxury accommodation, and it certainly lives up to its name. This 120-year-old mansion first served as the home of a local coal baron, was later sold and turned into an insurance office (with 120 employees!), and has now been returned once again to its former glory. And this time around, it’s not a private home; and everyone is welcome. The property now operates as a Bed & Breakfast and also doubles as an event space for small weddings and celebrations.
We had the pleasure of staying here for two nights, and from the moment we pulled into the parking lot, we were greeted with nothing but warmth and hospitality. The Estate is owned by a husband and wife team who’ve completely restored it and made it their own with old-world charm and opulence in mind. We were given a tour upon checking in and could see instantly how much heart went into making the Estate what it is today.
We promise you, you will not find kinder, more thoughtful hosts, and a stay at The Grandeur Estate is worth the trip to Greensburg alone. Breakfast was impeccable, our room was beyond cozy, and we’re pretty sure no request was off the table should we ask, but of course, we wanted for nothing; they had already thought of everything.
Enjoy Locally-Brewed Beer
The region is home to over two dozen breweries, and even more wineries, cideries, and distilleries, so you won’t have any trouble finding a place to enjoy a local craft beverage. If you happen to need an incentive beyond supporting local brewers to visit these establishments, you can pick up a Laurel Highlands Pour Tour Passport (or download one digitally) and earn prizes as you sip and savor. This program runs January through December each year. We had the chance to try out two breweries on our most recent trip; both of which are worth adding to your list.
Yellow Bridge Brewing‘s mission is to bring top-notch beer to Western Pennsylvania, and that they do! This family-run establishment is open Wednesdays-Sundays and serves up some delicious pizza (of both the circular and rectangular varieties) in addition to craft beer. We both opted to order their seasonal pours, mainly because of their fun names like Reinbeer Games and Midnight Gingerbread.
Dine in an Igloo at El Diablo Brewing Co.
Speaking of breweries (and pizza), El Diablo Brewing Co is another must-stop. We were told by no less than seven people that we needed to order their Gojoujang Califlower, and it definitely lived up to all the hype. In addition to the best cauliflower we’ve ever tasted, we split one of their wood-fired pizzas (also delicious). Aside from that, they have a full menu with a variety of tacos, sandwiches, and proper entrees. This place is a local favorite, so definitely make a reservation if you want to sit down for a meal or reserve one of their festive, outdoor igloos.
Catch a Show at The Palace Theatre
Celebrating its 100th birthday in 2026, experiencing a performance at this historic theatre makes for a wonderful addition to any Greensburg itinerary. We enjoyed a performance by the River City Brass Band entitled “Christmas Brasstacular” and were captivated the entire time.
Maestro James Gourlay was energetic and quite funny, and his love for his work was undeniable. Santa even made an appearance! We highly recommend catching a show here, if you get the chance while you’re in town.
Enjoy Breakfast and a Slow Morning at The Graudeur Estate
Breakfast is the main event here, and should be savored. We enjoyed freshly made, warm, cheesy bacon egg bites, avocado toast, and an assortment of fruit, pastries, and coffee and tea to start our day. Breakfast is served B&B style, so you will likely be seated with other guests of the Grandeur. Use this opportunity to chat and connect with your fellow human beings you share this space rock with, who knows, you may even learn a thing or two.
Take a Stroll around Twin Lakes
After check-out, take the opportunity to soak in the beautiful, snowglobe-esque local scenery one more time before heading home. Sarah, of @SarahLovesYinz says…”I think that sometimes Twin Lakes is really underrated and underappreciated for what it truly is, and it’s a really great park in all seasons. If you want to get outside on roads that are likely maintained enough, this is a great spot. Mix it up by heading off the lake paths and onto the trails.
You can always treat yourself after with a visit to one of the many coffee or tea spots we have! In no particular order (she recommends): White Rabbit, Dv8 Espresso Bar & Gallery, Steep Mountain Tea Company, The Trendy Bunny Event Cafe, Caleese, Cutie’s, & Caffe Barista.“
Looking for More Fun Things to do for the Whole Family?
Our friend, Kim, of @KimHikedIt is an avid hiker and local mom of five and has plenty of recommendations for active families visiting Greensburg. She says…
“Winter in Greensburg doesn’t slow us down. We stay active with walks or runs on the Five Star Trail, (one of the only trails in the state that operates next to an active railroad), often followed by a stop at Pizza Siena, a family favorite.
When we’re looking for indoor fun, we head to Main Bowl for bowling, the Kirk S. Nevin Arena for ice skating, or 60 Minute Missions for an escape room. No matter the season, there’s always something to do in Greensburg.“
Western Pennsylvania is filled with hidden gems, and Greenburg is no exception. As Kim said, this little city has no lack of fun things to do, no matter the season! We hope this list can help inspire your next trip, and that you have just as much fun in this charming region as we did!
